Podcast Ep.126 – When should you bring up things like marriage & kids when dating? – Pt. 1

I called in a guest host for this episode and the episode ended up being so good and so long, we had to split it in TWO. You may recognize my guest host from episode 114, Talk Poly to Me, Perhaps Perhaps, aka @PolyGalSeeks on Twitter. In this half of this two part episode, we took a larger question about the timing around bringing up marriage when you first start dating and tried to tackle it from every angle. We start small, by asking how soon you should bring up pets, and work our way up to marriage and kids. Wondering how soon you should bring up the fact that you don’t want kids, or your bad credit, or even whether or not you should move in together and where?

If you want our answers, Press Play:

If you enjoyed this episode you can subscribe to the podcast on iTunesStitcher, or Google Play Music.

Good Luck Out There.

Intro song: El Mariachi by The Freak Fandango Orchestra
Intermission song: Traffic Isle (ID 466) by Lobo Loco

There isn’t one reason dating isn’t working for you

Hey, it’s Demetrius, how’s it going? I hope you’re well. Listen, I keep hearing people asking why dating isn’t working for them, and I’m seeing a lot of different reasons why from people from all walks of life. Hell, if you ask me on any given day why dating doesn’t work, I’ll give you a different answer. “You aren’t putting yourself out there” or “You’re too hung up on an ex” or  “You’re not being realistic”. There’s always a reason that people will tell you why dating isn’t working. Especially dating “experts”.

There isn’t one reason dating isn’t working for you.There isn’t one specific thing holding you back from your dating goals, it’s a whole bunch of factors. No one, myself included, has the complete answer for why dating isn’t working for you. Anyone who speaks with absolutely certainty about why dating isn’t working for you is probably, by some strange coincidence, trying to sell you a product that addresses that specific issue. Funny how that works, right? Anyone who doesn’t know you personally is only guessing why dating isn’t working for you, and I’d be wary of anyone who tells everyone the same reason why dating isn’t working for them. “Dating isn’t working for millennial women because they intimidate men” is a common one I’m sure you’ve heard. Maybe you’ve even heard that dating doesn’t work for modern daters because online dating by its nature doesn’t work. Trust me when I say that I’ve heard all the reasons that dating isn’t working for people, and while some of the reasons can be true, rarely are any of the reasons universally true.

I write dating advice on a pretty frequent basis and I make no claims at all that I’m always right, or that there is always one right answer. Anyone who tells you that dating isn’t working because you’re not feminine enough, or too successful, or too educated, is just showing you their own dating biases. People who tell women they aren’t feminine enough are often the same people who benefit directly from telling women they aren’t feminine enough. People who tell men they aren’t skilled enough at picking people up in public are often the same people who sell them guides on picking people up in public place. You don’t intimidate men, you intimidate *some* men, but you have to ask yourself if you would you rather choose being single or date a man who doesn’t appreciate who you are. All women aren’t looking for guys with tree-trunk arms, a red room of pain, and a hipster haircut. Some are, and some aren’t, and you really aren’t missing out on dating someone who doesn’t want to date you.

There are some things you can fix that might be holding you back from succeeding at dating, but odds are good that they’re only a small part of why dating isn’t working for you. If you aren’t finding luck on dating sites, and your profile is sparse, fill it up with things that can lead to conversations. If you’re going on a lot of first dates that don’t lead to second dates, try to figure out why that might be and address it. It could be that your dating profile doesn’t accurately reflect your personality, your values, or how you look. If you’re not dating online, are you putting yourself in positions where you will meet new people? You’ll be single for the rest of your life if you’re never in a position to meet anyone, online or offline.

I brought this all up to tell you that you’re probably way too hard on yourself about something that is mostly out of your control. There might be someone out there that is perfect for you, but circumstances just haven’t brought you together yet. Oh, and it’s not just one person whose a good fit for you, there are tons of people out there that are perfect for you, you just haven’t crossed paths yet when you were both available. There are some things that are within your control in dating, so my advice is tackle what you can, but don’t stress out about the things outside of your control. You’re not single because you’re not ridiculously fit. You’re not single because you’re highly successful. You’re not single because you’re tall, or short, or slim, or curvy, or overweight. Some of those factors might be why specific people didn’t want to date you, but they aren’t an indicator of your worth as a person.

Being single isn’t an easy fix, because dating and relationships take work. And finding someone to even make dating work with is up to chance. You can be the best looking, most eligible single person in the world and if all you meet are married people, you’ll be single forever. Whatever you take away from this just know that if dating isn’t working for you, it’s not just because of one reason. More importantly, there’s nothing wrong with you if you’re single.

Good Luck Out There.

Do you have to be good at cold approaching women to succeed in dating?

Himalayan_Hillbilly asks:

So basically every piece of dating advice discusses how you need to get comfortable approaching women whenever and wherever in order to get good with women. However, I have a number of buddies who are really good with women, and I don’t think any of them would be comfortable with just walking up to a random person on the street and talking to them and asking them out. Is this really that important or are there other more important pieces? Continue reading

Podcast Ep.125 – Do you feel like a stepping stone for your Exes?


This week’s episode is a good one, and we hope it was worth the wait. Do you ever feel like you’re a stepping stone for your Exes to find someone better than you? Do you ever feel like the “starter” relationship?  Do you ever feel like you’re helping people find bigger and better things, while you get left behind?  If you’ve ever felt that way, trust us, we understand where you’re coming from. Let us talk it out with you, and see if we can change your perspective a bit.

Press Play:

If you enjoyed this episode you can subscribe to the podcast on iTunesStitcher, or Google Play Music.

Good Luck Out There.

Intro song: Drinks (4am rmx by Dominik Berlin) by Spiedkiks
Intermission song: Тоска by pavlove

Should I wait to see if this guy changes his mind about relationships?


aqua_not_capri asks:
I’ve known this guy for two months. I wasn’t expecting anything to happen but I fell for him. We’ve been talking and he likes me, but he hadn’t been looking for a relationship either and didn’t expect to like me this much. He doesn’t know where this is going to go and has just been enjoying it. As of right now we’re just hanging out and keeping things light.
I know that two months is a very short period of time so I’m not expecting a relationship right now. But as of right now he’s not sure if he wants one in the future. I’ve never been in this situation before. I want to stick around and wait because I have some strong feelings for him. At the same time I don’t want to waste time. I thought about meeting other people while keeping him around but I’m a one-person-at-a-time girl. I’m really stuck. Continue reading

These dating questions brought you here, so let’s answer them


Hey, it’s me, Demetrius. How’s it going in your part of the world? Listen, I’m going to level with you, writing 5 days a week can get a bit exhausting and at some point, I flat-out run out of things to write about. Luckily, that’s where you all come in. And by you all I mean people who use the internet to answer their dating questions.

Some of you are finding the blog in interesting ways, which I thought I’d address. Don’t worry, I can’t see who is searching the internet asking these questions and find my blog, but I know a bunch of you are. So let’s answer your burning questions: Continue reading

You’re recently single, now what?


Breakups, no matter the level of seriousness of the relationship that preceded it, are rarely fun. At some point, you wanted things to work out in your relationship, regardless how it ended. Whether it was a short relationship, friends with benefits, a marriage, or anything else that brought you here, welcome. You’re recently single, things have probably changed a bit since you were last single, and now you’re wondering what to do.

Okay, here goes. Something to keep in mind before you read any further, these are my tips. What they are not is gospel. Take what works for you, disregard what doesn’t. ✌🏼

First, let’s talk about Social Media:

I’m a big fan of purging your social media of any trace of your ex, and would encourage you to do the same. That might be easier for me than it is for you, but trust me, it is a big help in getting over the last person you were seeing. You probably use Facebook right? How awful is it going to be when, a month after a break up, they show you a memory from a year ago where you and your ex are being all affectionate with each other. Spoiler Warning: It’s going to suck so hard. Seriously, give it a shot. Delete them from your social media. Delete posts about them. Delete the pictures you have together. Out of sight, out of mind.

Next up, let’s talk about grieving:

I’m a big believer in taking a break from dating after a break up for a lot of reasons. First, you really should do a very clinical and dispassionate look at why things ended. Did they really end just because you drifted apart, or did you miss the warning signs all along that you just were never a good fit. Did you really break up because you just were fighting too much at the end, or were you fighting the entire time, and you finally had enough. There comes a point where you need to look at your relationship for what it was, warts and all. Next, take some time to really grieve for the loss of your relationship. Even if they were just the worst goddamned person in the world at the end, at some point you cared for them. If nothing else, grieve for the version of yourself that cared for them. Finally, and most important, take a break from dating. Give yourself time away from dating to just sort of center yourself again.

Next, let’s talk about whether or not to Date Online or Not:

Really quick, I want to address a conversation I see play out fairly often. There is this persistent belief among some people that dating online will inevitably end in failure, primarily because there are so many options, no one ever wants to settle down. The thing is, that might be true of some people, but it’s definitely not true for everyone. Almost every single person I’ve dated seriously is someone I met online. The last wedding I went to, want to know how they met? Online. Obviously it’s not true that every single person who dates online is always looking for the next match. One other thing to remember, if your thinking is that YOU wont date online because everyone is just too picky so they’ll never settle down…you know that doesn’t mean that the people you meet offline aren’t dating online, right? It’s not like there’s something stopping people who date online from meeting people offline, you know that right? Now, if you don’t want to date online because you’ve consistently had negative experiences doing it, by all means skip it, but don’t NOT date online because someone told you it was terrible.

If you’re looking to date, casually or otherwise, my advice is to use every single tool you can to your advantage. Date online, use a matchmaker if you can afford it, ask friends about their hot friends, approach people at singles bars/events, use everything at your disposal to meet someone who you feel comfortable doing. Don’t assume that you have to date online, and don’t assume that because you are dating online that you can’t find someone through friends or coworkers. Whoever you are, I think you should date online, or at the very least give it an honest try. You don’t have to dedicate yourself to ONLY dating online, that’d be silly, but why not try it. Most of the biggest and best sites and apps are free, and take about 5-15 minutes to sign up for, so what do you have to lose? If you end up not liking the experience, delete your account.

Last but not least, something to remember:

Being single isn’t an identity you need to associate yourself with if you don’t want to. You’re probably a halfway decent to pretty awesome person (which I feel safe in saying because my readers are wonderful), who just happens to be single now. It’s not an indication of your worth as a person. There’s nothing wrong with being single, and there’s nothing inherently wrong with you because you’re single. You’re worthy of love, of finding someone who is a fit for you, you just haven’t found them yet.

Good Luck Out There.

How do I know if I should settle?


As a man of the people, sometimes I like to crowd-source sex, dating, and relationship questions. One such question I asked for and received was from PolyGalSeeks, who you might remember from Episode 114 of the podcast, Talk Poly To Me. I asked for a dating question, and she delivered:


PolyGalSeeks asks:

What if I am dreaming too big? How do I know if I am throwing away something great and maybe I should settle instead?

Continue reading

What are some things to keep in mind when moving in with your partner?

So today, I had a bit of writer’s block today, so I asked Twitter for some help. Luckily, I have the good fortune to follow and be followed by some awesome people, like Jenn from the blog Jenn and the City, where she covers just dating, life, love, relationships and everything in between. And I do mean everything, her most recent posts are about dealing with depression and Valentine’s Day date ideas for whether you’re coupled up or solo.

Anyway, I asked for a dating question, and she gave me a few really good ones, one which I’m answering in this post.

Jenn asks:

What are some tips and tricks and things to keep in mind when moving in with your s/o? Continue reading

Anyone else feel like their exes use them as a stepping stone?


PathologicalFryer asks:

Every time I break up with someone, the next guy my ex-girlfriend dates is taller, more athletic, more attractive and smarter than I am. Why would anyone ever consider settling for me if it appears I’m just the bottom rung on the ladder to Prince Charming? I’m trying to work on myself a lot (making more money, working on physical appearance, health, etc.) but I fear even if I optimize myself it’s still never going to be enough to be worth anyone else’s time. Continue reading

Is it weird to mention that I’m looking for someone to share my hobbies in my dating profiles?


paulrobert89 asks:

Is it weird to mention running and looking for a running partner in my dating profiles?


So I’ve been a runner for most of my life and try and run 3 times a week or more. I’m only using the tinder app right now and haven’t really found anyone with a lot of my common interests. I figured I should change my profile so that mentions a hobby of mine : “Hey y’all recently returned from living in Europe and just on here looking to meet people and see where it goes. Oh and my favorite hobby is running! If anyone is looking for a running buddy let me know!”
I was just wondering if that seems like an ok thing to put in and not too weird. Thanks! Continue reading

Podcast Ep.124 – How should I Break-Up with my Girlfriend?


In this week’s episode we answer a question about breakup etiquette. What would you do if you wanted to breakup with your partner of 3 years, but the only way to do so in-person would require a 7 hr drive for one of you? Would you have them drive to you so you can break up with them, call them and breakup with them over the phone? Or would you do something completely different?

Want our answer?

Press Play:

If you enjoyed this episode you can subscribe to the podcast on iTunesStitcher, or Google Play Music.

Good Luck Out There.

Intro song: Where the Sunshine Goes by Yshwa
Intermission song: Solid Armada by Bouwakanja

How do I let a friend know it’s too hurtful to remain just friends?


duttyrage asks:

How do I let a friend know that it’s too hurtful to remain just friends after she friendzoned me?


I’ve developed genuine feelings for a friend. I’ve gradually escalated and expressed signs of interest and she reciprocates. We both flirt with each-other, I make her laugh and I’ve found surprisingly that she is extremely comfortable with me touching her, (especially in the thigh and knee area, and me resting my leg on her leg) which lead me to think that there may be something more between us. She eventually texts me “would you like to go out to the movies as friends” to which I agree too.
In short, we had a great time with all the physical touching, and flirting included. I text her letting her know I had a good time and she texts me “Hey I had fun today too fam. night bro, have a good one dude”. I have become really invested in our friendship, but it truly hurts to receive this text knowing what she meant by this. It’s become unhealthy where I over think and over-anaylze things too much ever since she reciprocated my signs of interest. I now however have a little over 10 days before I see her again which will help me get over her.
However, at this point I know the friendship will always remain unbalanced as I feel frustrated that she will only ever see me as a friend. Will giving her an ultimatum do anything for my favor, or will just letting her down gently in explaining why we can’t be friends be better? I want to make it very sincere that I do value our friendship, but would also want to let her know that I’m continually hurting. Continue reading

How do I “man up” and ask a girl I like out?


Askoutagirlthrowaway asks:

I’ve known a girl in my class for a few months now, we get along and I just want to ask her to do something with me. I tried doing it today but backed out just become I’m scared & a little awkward I know she likes me as a person (I can make her laugh), but I don’t know if she “likes” me. Any suggestions? Continue reading

Valentine’s Day is Just Another Day


Hey, it’s Demetrius. How are you doing? I hope you’re doing well, but its okay if you’re not. Especially if the reason you aren’t doing so well is because it’s the eve of Valentine’s Day, and you’re feeling a bit down about the day and all the baggage it brings. Maybe you’re feeling lonesome, maybe you’re angry, or maybe you’re still feeling resentful of the people you’ve dated in the past, and those feelings are all the more magnified because of the cultural significance of the day. I’m not here to tell you those feelings are invalid, I just want to remind you of something. Valentine’s Day is just another day.

Look, I understand how much weight Valentine’s Day holds, both positive and negative, but please believe me when I tell you that it’s just another day. There’s nothing wrong with being single on 2/13, and there’s nothing wrong with being single on 2/15, so if you’re feeling down because you’re single on 2/14, you’re buying into the hype of Valentine’s Day, and you should stop. Your relationship status on Valentine’s Day is not a measure of you as a person, or even as measure of your worth as a potential romantic partner. If you’re single on Valentine’s Day, it just means that you’re single on a specific day of the year, one that we’ve come to associate with romance. It holds no deeper meaning than that. Being single on Valentine’s Day is like being sober on St. Patrick’s Day. While it might feel like everybody else is in a different position than you, it doesn’t mean that there’s anything wrong with you.

Personally, I’ve always had conflicted feelings about Valentine’s Day. The marketing, the commercialization, the forced effort, but most of all, it’s a day of loss for me. It’s the day I buried my father, more than 20 years ago, so believe me when I say I’m not the hugest fan of the day in general. But you know what, it’s just a day, even for me. It’s the 45th day of the year, nothing more. It’s a day to celebrate the Christian martyr Saint Valentine of Terni, whose martyrdom has dick-all to do with love, romance, hearts, or Cupid. It’s a day that most likely came to be associated with romantic love because of Geoffrey Chaucer, because of the poem “Parlement of Foules”. It’s the day that Al Capone seized control of organized crime in Chicago. It’s the day that YouTube was launched in 2005 (as a dating app!).

The only significance that the day has is the significance that you allow it to have. You have every excuse to let the day get you down, or you can decide that you won’t let the day ruin your mood. You can let being single, or in a nebulous relationship status on Valentine’s Day ruin your day, or you can just focus on the happiness you do have. You can spend the day envious of your coworker who got a bouquet, or realize that getting the sex organs of dying plants is such a weird gift to begin with. You can spend the day lamenting the fact that no one got you chocolates, or find comfort in the fact that ALL VALENTINE’S DAY CANDY GOES ON SALE THE NEXT DAY. I could easily spend the day, every year, dwelling on the loss of my father, or I can enjoy the day for what it is, an excuse to blog.

The choice is yours. Just remember that Valentine’s Day is just another day. It’s a day that means whatever you want it to mean. It can mean a yearly reminder that you’re single, and a failure in your own eyes if you let it. Or, it can mean that you refused to settle on being with just any old warm body. It’s a day that can be filled with “what ifs”, or it can be a day filled with being at peace with being alone. It can be a day to lament being single, or a day that helps you put being single in perspective. It ain’t all bad, trust me. I spent years being single on Valentine’s Day and all I got out of it was the loyal readership of all you folks, and that’s worth way more than a dozen, 200% marked up, roses.

Whatever you decide, just remember: It’s just a day, and it’s okay if the day is hard for you. Just don’t let your relationship status get you down.

Good Luck Out There.

Podcast Ep.123 – How much should I disclose about my past affairs?


In this week’s post we answer a listener’s question about honesty, when it comes to his past infidelities. If you’ve cheated in the past, and that’s why your marriage ended, how honest do you have to be when you start dating again about your infidelities? How do you avoid losing someone because of your past, and how do you let it go?

Want our answers?

Press Play:


If you enjoyed this episode you can subscribe to the podcast on iTunesStitcher, or Google Play Music.

Good Luck Out There.

Intro song: LahLahLand by Ghryzly Atoms
Intermission song: humm ok by Gablé

Do I wait for him to ask me out on Valentine’s Day?


Throwuhway88 asks:

I’ve been dating this guy [28] for almost 3 months, and things are going well. Last night it was his birthday and planned something for us which he really appreciated and we had an awesome time. We kissed goodbye at the subway station and he held my hands and said he would see me when he gets back (he is going on a trip and coming back Mon. morning) and then we kissed again and he said “see you next week” and saw me off to my train. We sometimes make plans for a specific day for the next date, but not if one of us is traveling or we’re really busy, etc.

However – Tuesday is Valentine’s day, and I know that’s not even a real holiday, but I’ve never been dating someone during V day and think it would be kind of nice to do something. But I don’t know how to approach this. He’s flying out tonight and will be busy all weekend until he flies back Monday morning. So I could just wait until Monday to see if he asks me about V day but at the same time I don’t want it to see like I’m just sitting here waiting for him to ask when he probably won’t have time to think about it until Monday. Should I ask him or just leave it?

Continue reading

Podcast Ep.122 – 7 Things That Can Ruin A Relationship


In this week’s episode we discuss 7 things we think can ruin a relationship. Whether it’s incompatible sex drives, a lack of trust, or messy behavior on Instagram, of which I am guilty of because I like to stir the pot, there are plenty of ways that a relationship can be ruined, and we dive into them all.

Press Play:


If you enjoyed this episode you can subscribe to the podcast on iTunesStitcher, or Google Play Music.

Good Luck Out There.

Intro song: Lift Off by Jahzzar
Intermission song: Rio Bravo 1 (ID 427) by Lobo Loco

10 Dating Questions I Always Get Asked, Answered

Hi, I’m Demetrius. I’m  a Sex, Dating, and Relationship advice writer and podcaster. You might recognize my work from this very blog, or my contributions to other blogs and publications. If this is the first post you’re reading of mine, welcome! Don’t worry, you don’t have to read every single post I’ve written (there are well over 500 posts) or listen to every single podcast (there are 120+ episodes). That would be a hell of a lot of work to ask of you.

If you’ve come across my work randomly, you’ve probably got a few dating questions you’d like answered. I’m no expert, I just think I give solid, no-nonsense, objective advice, but believe me when I say that  I don’t have ALL the answers, and I’m not infallible. But, because I write (and podcast) so much, there’s a chance I’ve already answered a question you have, or covered it in some way. Rather then sending you to search depths of my archives, let’s assume that you’re like so many people, and you’ve come here to get the answer to one of these ten questions I always get asked: Continue reading

Can I ask out a guy I unintentionally ghosted a year ago?


atlisse asks:

We met online and agreed to meet for coffee. The date went amazing and we definitely had chemistry. We hung out for 6 hours as opposed to the 1 hour coffee chat we had planned. He texted me later asking me on another date, and I replied that I’d love too. Two days later I got into an accident and had to spend 2 months in the hospital, where I couldn’t use my phone or the internet. When I finally got out, I texted him telling him I was sorry for wasting his time, and if he wanted we could go out again. He said he’d met someone else in that time.

Fast forward a year to present day and I recently found a new hobby that he had mentioned during the date. I really like it, but it’s made me start thinking about him again. I found out he’s single and I’d really like to ask him out again, I think we had amazing chemistry, but not sure if that would be weird or if I’d scare him away…. I’d like some advice.

Thank you!

Continue reading

If they want to be friends before dating, should I still see them?


I’d heard from an early age that the best way to build a long and happy relationship was to establish a friendship first. I’m still on the fence. I’m of the mind that you should consider your partner a friend, but I don’t think that you have to go out of your way to be friends with someone first before jumping into a relationship.

But, I’m not infallible, so let’s look at both sides. Continue reading

7 things you can do when you’re “too busy” to date


I’m a pretty busy guy, and I’m guessing that you, like many modern daters, are pretty busy too. Between my day job, writing, and podcasting (you’d be surprised how long it takes to edit 15 minutes of audio), it’s hard for me to find time to go on dates. I’m guessing that you’ve probably got a lot on your plate too. So many of us are trying to balance working long hours, engaging in activities that keep us sane, and social demands that dating is often something that we’re “too busy” to do, or to do it well. But you know what, I think you can do it. But it’s gonna take some work. Here’s how to do it: Continue reading

Guest Post – 6 Ways Guys Ruin A First Date Before It Even Happens

For a woman in the online dating community, it’s easy to become discouraged with the numerous faux pas men are guilty of in the dating pool. Impressing a potential mate on a first date is imperative in the courting process, but there are a few ubiquitous acts of self‐sabotage you can commit before you even make it to your date. Here are six all‐too‐common mistakes that can be easily avoided to achieve a more positive first impression. Continue reading

Podcast Ep.121 – Why do some people rush into relationships?


This week we wanted to talk about rushing into relationships. What is it that makes people want to rush into a relationship? What drives people to decide after the first or second date that they need to dive headlong into a relationship? What sort of person wants to rush into a relationship? More importantly, why you should wait even if you are sure about someone after the first date.

Plus, insight into what it’s REALLY like to date Demetrius, why being perpetually in a relationship might be hurting how you view dating, and more.

Press Play:

If you enjoyed this episode you can subscribe to the podcast on iTunesStitcher, or Google Play Music.

Good Luck Out There.

Intro song: How Exciting by Revolution Void
Intermission song: Weekend Amnesia by Revolution Void

Here’s how to make your online life a little less stressful


Hey there, it’s me, Demetrius. How’s it going? I’m doing well, all things considered, but I’ll be honest with you. A lot of what I’m seeing online is stressing me out. I’m worried about people losing access to healthcare. I’m worried that children fleeing a war zone will find no succor nor safe harbor in the one place that should be a shining beacon of hope to the world, and I’m worried that none but those at the height of wealth and power will have their lives bettered over the next 4 years. How about you, feeling the same? I hear ya, trust me, it’s a stressful time. There are some realities you just cannot avoid, but what you can avoid is letting your online life stress you out. Full disclosure here, these are things that I do, so I’m not guaranteeing that they’ll work for everyone in equal measure. That said, here’s how to make your online life a little less stressful* (*results may vary, obviously) 

Continue reading

How do you move from matching on a dating app, to texting, to a first date?


Let’s take a little break from dating and relationship advice that deals with the tough issues, and let’s just talk about actually getting on a date after matching on a dating app. Chances are good that if you’re reading this, you’re on at least one dating app. Chances are also good that the whole online dating process doesn’t feel natural. Dating norms are incredibly varied to begin with, once you add in an online element, all bets are off. Just think about the way we communicate and get to know people on dating apps and how vastly different it is compared to meeting people in real life. There is no swipe right in the real world, at least not that I’m aware of, but even things like opening conversations look very differently when you compare online dating to offline dating. You’d never approach someone at a bar and ask them how their week was, you know?

It’s perfectly okay to not be knowledgeable about online dating customs, because if we’re being honest, they don’t really exist outside of basic norms around decency, which are largely ignored. If we ever do come to an accepted consensus on what’s an online dating norm, they’ll eventually grow and evolve in the same way that offline dating customs grow and evolve year after year. And that’s usually a good thing. Personally, I’m a big fan of the fact that I don’t need to provide oxen as a bride price, because I’d be at a loss as to where to even get live oxen in New York City. (I’m kidding, I’ve got a guy who works at a vivero that can get you live oxen if you give him a day or two heads up). In all seriousness, people’s unfamiliarity with how things should progress in dating is completely understandable, even more so with online dating. Which brings us to getting an offline date.

Most people on dating apps share a common goal: To go on a date. Sadly, many people are clueless about the best way to get your online crush on an offline date. Luckily, I know a thing or two about transition from a dating app, to texting, to a first date. It’s not rocket science, and honestly, the hardest part is getting people to even respond to you once you’ve matched. Once you’ve done that, it’s a lot easier than you might think to transition offline. So, here’s how I do it. I think this approach would work for you too:

Transitioning from the Dating app

This part of the post is going to make three assumptions. First, that anyone regardless of their gender or sexual orientation can and should initiate transitioning from a dating app or website to another mode of communication. Don’t wait for them to initiate because of some outdated (probably gendered) rule, fortune favors the bold. Second, let’s assume that you want to transition from a dating app to communicating by telephone prior to a date. If you don’t want to do that, the advice still applies for the most part, just do all the steps on the app itself. If you do want to transition from a dating app to, let’s say email, this advice applies too, just swap out “phone” for “email address”. Third, let’s assume that your goal here is to go on a date with a potential for future romance, and not a quick hookup or to make a new friend. Some of the advice might apply for both of these scenarios, but a lot of it won’t. If you want specific advice for transitioning offline when your goal is hooking up, making friends, or something else, you can always email me or DM me on Twitter.

With that out of the way, here’s how your transition from a dating app to communicating by phone:

  1. Establish attraction and screen them. In those first few messages, your goal should be to try to get a read on the person you’re messaging. If you get a bad read on a person, trust your instincts. Whatever initially attracted you to their profile and their pictures, now’s the time to confirm that attraction and build on it. Or, figure out if you read them completely wrong. You’ve probably got some immediate deal-breakers, so now is the time to figure out if they make the cut. Also, make sure that you clear their deal-breakers. I’ve been on a few dates with women who, only while on the date, revealed that something about me was a deal-breaker, whether that was religion, my ethnicity, education, or career. Besides that, just try to establish a basic comfort level when communicating with them. If they can’t hold a conversation with you over a dating app, odds are good that they won’t be able to have one with you over text*.
  2. Make sure your conversation is progressing. There are lots of people out there who will message you after matching, and keep responding to your messages, with no real desire to ever actually meet you. Take for example the bizarre exchange between Michael Che and Leah McSweeney. Opinions on his texting etiquette, or her saying that some men “look gay” as a pejorative aside, their conversations can tell you a lot. Che responds to McSweeney even though I’m sure that at least after the first exchange, he’d already decided that he wasn’t going to meet her. (Probably because she’s the sort of garbage human who uses “gay” as a pejorative). If your conversations on dating apps seem to have the same sort of feel as the conversation in that article, with lots of back and forth that doesn’t seem to progress, transitioning to texting might be pointless. If your conversation seems to build in a coherent way, consider transitioning to texting. If you’re unclear on what conversation progression looks like so here’s a basic idea of what a conversation that progresses looks like:  You mention a topic. You both talk about that topic using more than just one word answers. You ask about something related. You both talk about that topic using more than just one word answers. Rinse and repeat.
  3. Hint at a date, offer to exchange numbers. After you’ve done all the hard work, now it’s time to pull the trigger. Asking for someone’s number while also floating a very rough draft of a date idea is something that I’ve found works really well. It can be as simple as saying “Hey, remember when you mentioned that you love whiskey? Well I know a bar that has an awesome selection, and I’d love to take you. Want to plan a date over text?”. There is always the risk that whenever you ask, whether it’s after one day or one week of texting, they might consider it “too soon” to exchange numbers. As I mentioned before, no set dating norms for online dating means everyone has their own idea of what is “too soon”. If you feel like you’ve done a good job of screening someone, and think you want to move to date planning within the first day or two of messaging, go ahead and ask to exchange numbers. On average, it usually takes me somewhere between 2-5 days of messaging, or about 5-10 or so conversation smaller conversations to get to this point.If you’ve been messaging for a month without exchanging numbers, you should consider that a warning sign that they might not want to meet you. I’m not saying that you need to meet within a month, but in my experience someone who isn’t ready to even start the discussion on meeting within 30 days of messaging is likely to not be serious about meeting.

*There will be exceptions, because some folks are bad at texting. If they tell you this, your transition to the phone should probably be geared toward calling them. If they’re bad on the phone as well, they might just be bad at communicating with you.

Transitioning to meeting in person

Okay, so you’ve done your pre-screening, and you’ve decided, screw it, they seem fairly not murder-y, might as well exchange numbers. At this point your focus really should move toward date planning. Here’s how to do that:

  1. Preparation. At this point, build on the conversations you’ve already had, and the one where you floated a date idea and start figuring out when you’ll meet and what you’ll be doing. This is another area where people’s ideas of what’s a dating norm differ drastically. A lot of the time, you’re proposed date idea doesn’t actually work for your first date, and you may get push-back for the activity you suggest. I’ve had potential dates shot down because someone thought the idea of getting drinks on a date was too cliché, and I’ve also had people shoot down really cool and innovative date ideas. My advice is propose a date you’ll feel comfortable with, and if they don’t like the idea, have another idea ready, or ask for a suggestion. Personally, I’m of the mind that if I come up with an idea for a date, and someone doesn’t like it, they should collaborate with me to come up with an idea they’ll enjoy, and not keep sending me back to the drawing board with no feedback. But, I’m not one of those people who thinks it’s ALWAYS up to the straight man to do all the heavy lifting for date planning. So, your results will vary. Ask them when they’re available, float a date idea and build from there.
  2. Confirm your date. Chances are good that there are probably a couple of days between when you get their number, when you start planning your date, and when you’ll be going on your date. If you’re date is the next day, confirm your date at the end of your conversation. If it’s 2 days or more between date planning and the day of the date, send a confirmation text on the day of your date, preferably in the morning, so that they know plans are still on. People are flaky as hell these days, and I’m willing to bet that many of you reading this have been cancelled on within an honor or two of a date. The best way to put people at ease, and make sure you don’t show up to a date that they thought was cancelled because you never reached out, is to reach out and confirm your date the day of your date. Doing this will serve a few purpose. First, it’s a confirmation, Second, a reminder, and Third, a chance for them to back of the date as early as possible so you have an opportunity to make alternate plans. Don’t send a text saying “Just confirming our plans tonight”, do send a text that says “Hey, looking forward to seeing you later at {Date Venue}”.
  3. SHOW. UP. TO. YOUR. DATE. You don’t need me to explain this, do you? In the rare instance where you can’t show up for a date, but you are legitimately interested in rescheduling, reach out to them as soon as possible, apologize for the inconvenience, stress that it’s a serious issue and you want to reschedule, and have a date already pre-planned to show that you’re serious.

Now, all you have to do is show up and be as charming and witty as you were on the app and over text. It should be no sweat.

Good Luck Out There.

Have you ever slept with your roommate? What should I do?


Brian from Ohio asks:

I met a girl a few years ago. I was attracted to her, but she had a boyfriend at the time. We live in the same city, and would see each other in bigger groups occasionally. When she broke up with her boyfriend I was dating someone else. I eventually broke up with that girlfriend, but for some reason assumed the first girl wasn’t into me.

About 5 months ago her lease was almost up. I live in a 4 bedroom apartment, and she asked if there were any spots available. The timing was great because one of my three male roommates was moving out and we needed a replacement, so she moved in. Once we lived together we started hanging out more over the next few months: going hiking, going to the farmer’s market, getting beers together — all things I used to do with my male roommates, except since I’m a guy and she’s a girl sometimes it felt like we were on dates.

The lines started to blur a little more: sometimes if we were drunk we would cuddle on the couch when we were watching Netflix. One night I went in for a kiss, but she didn’t want me to kiss her, so I assumed she wasn’t attracted to me.
Then, a few weekends ago we were out with some friends and she was touching me a lot more and giving me signals like she actually was into me. The next night I went for a kiss and long story short we ended up having sex. The sex was really good (like one of the better times in my life, and I think I have a good amount of experience) even though it was only the first time between us.

I wasn’t sure if she wanted it to just be a one-time thing, but later that week we had sex again, and it was even better. I feel a strong connection with her since I spend a lot of time with her, and that might be why. So far we haven’t really discussed the relationship. I think I should probably talk to her soon and try to define the relationship, to see what she wants, since I’m not sure whether she wants to keep things casual and just hook up from time to time, or become boyfriend/girlfriend. It seems like this could end badly, since we live together, but I still think it’s much better than we cut the sexual tension by finally hooking up instead of trying to stay platonic.

Have you ever had a female roommate you were attracted to who was also attracted to you? What are your thoughts about this situation? What would you have done? Continue reading

Can you date someone if you have nothing in common?


Can you date someone if you have nothing in common?


It’s a question I’ve probably touched on in the past, but it’s been coming to mind recently. The short answer, as is often the case with so many dating questions, is “maybe”. Sure, you can date someone if you have “nothing in common”, but it really all depends on what you mean by having something in common. The fact that you’re alive means that you have something in common with billions of people right now, who are also are alive. If you’re reading this right now, you have something in common with something like 70%-80% of the world, who is literate. Having something in common is relative, you know? What people usually mean though is having specific common ground with a person.

Which is why I say maybe. I think that there are some things that, if you don’t have in common, you probably won’t be a good fit to date, and others that really don’t matter. What those things are, are things that you, as an individual place value on having in common. Let’s take your humble advice writer, Demetrius, for example. None of the people I’ve dated in the last, let’s say 10 years or so, have shared my interest in comic books. Maybe some have, but none to the same extent as I have. I’ve met plenty of people who are up for going to see the latest Marvel movie, but it’s rare that I meet someone who is as fascinated with the innovative visual storytelling of artists like Frank Quietly. Still though, I’ve never once felt like I couldn’t date these people because they weren’t singularly obsessed with studying comics. The reason why is because, although I love comics, having that in common with a potential partner is not something I particularly value.  The things that I need to have in common with a partner are things like empathy and compassion, not necessarily a shared love of pop culture. Look, I’m the sort of guy whose interests range from modern dating, the physics behind woodpecker skulls, fantasy football, the joys of modding games like Skyrim for infinite replayability, and the history of New York City. The things I value in a partner have nothing to do with those interests because sharing things like loving comics is cool and all, but I’d much rather date a woman who understands why I value family and friends.

So when someone asks whether or not they can date someone if they have nothing in common, I’ll always ask what they mean when they say “nothing in common”:

  • Do you mean that you don’t share the same hobbies?
  • Do you mean that you don’t share the same education level?
  • Do you mean that you aren’t on the same career path?
  • Do you mean that you’re not at the same point in life?

What matters to you in dating, is what matters to you, no matter how deep or superficial. What commonalities I value, shouldn’t determine whether or not you should date someone. The value you place on common interests is purely subjective, but that doesn’t mean that they’re any less important. If any of the things I listed above  are important to have in common with someone you’re dating, you probably wont be a good fit to date someone who doesn’t share those values. Personally, I’m most concerned with what point someone is in at their life, more than anything else on that list. I couldn’t date someone who doesn’t have that in common with me, but maybe you could. And there is nothing wrong with either of our valuations.

If tabletop gaming is something you’ve built your social life around, dating someone who doesn’t share that interest, or isn’t willing to learn about that interest, is going to be tough. If your identity is tied directly to your religion, dating someone who doesn’t have that in common with you will be difficult. If being heavily involved in Ivy League social circles is your thing, maybe you’ll value a common education path. What you value in yourself and in others is part of who you are. Each of us has SOMETHING that, if we don’t share with our partners, we probably aren’t a good fit. Whatever that is for you, big or small, superficial or not, it’s neither for me to judge, nor tell you whether or not it’s important to have in common.

How many interests you have in common doesn’t matter, what matters most is what you do have in common, and the worth you place on those common values.

Good Luck Out There.

Podcast Ep.120 – A listener asks: How soon is too soon on a road trip?



In this episode, we open up the Tao of Indifference hotline to answer a listener question about a very specific situation. How soon is too soon to have sex on a first date is an easy answer, sure, but what if it’s a crush from years past who you’re going on a road trip with? Trust me, we’ve got an answer.

Plus: Why you should always limit your liability on your own podcast, why “too soon” is a relative question with no real answer (with one big exception if you want a relationship), how awesome crossover episodes are, we confuse TaleSpin with Chip N Dale Rescue Rangers, post inauguration anxiety, and how hard it is to do the Hora.

And if you’d ever like to call or text us with a dating question, you can reach us at (347) 796-1864

Press Play:


If you enjoyed this episode you can subscribe to the podcast on iTunesStitcher, or Google Play Music.

Good Luck Out There.

Intro song: Duckin' & Divin' by Greater Than Or Equal To
Intermission song: Beloved Is He Who Sits Down by Geese (Warning: Song Artwork is very NSFW)

If she is always the first to view my Snapchat story. Is she interested?


youngth asks:

If a girl is repeatedly the first to view your snapchat story, is that any indication of interest?

Literally every single story I post is viewed by her first. I have a MASSIVE crush on this beautiful woman and I’m lost. I genuinely feel as if she is out of my league, but every time we see one another when going out we end up talking. I’m just a freshman in college with a huge crush, so don’t judge, haha.

Continue reading

Wanted to go for a kiss, couldn’t muster it. What should I do?


JawnOfArc asks:

So tonight was my second date with a girl I started seeing. The first date went quite well; we sat at a coffee shop for about two hours and had some nice, organic conversation with laughs and basically no silences at all. I’m pretty into her, and based on how frequently she’s been texting me, I think she’s pretty into me too. I was ready to go in for a kiss tonight assuming the date went well. As I expected, it went rather nicely. We bowled for an hour and walked around the mall a little, having nice conversation (and some friendly shit-talking) throughout. We both intentionally made physical contact at times during conversation. Anyway, she was my ride, so I planned on kissing her when we got to my building. We get there, and after I say that I had a good time, she immediately suggests we get together again later in the week. Awesome, I’m in. Or so I think.

I’m looking for a sign from her: extended eye contact, looking at my lips, something. But there wasn’t any obvious indication to go for a kiss. We hugged in her car, but after that she pulled away a bit too far for me to go in without awkwardly overextending. So we said “Bye” and she left.
Is she just shy? Things have been going pretty great, and she wants to see me again, so I don’t think she’s losing interest. How can I maybe be a bit more forward about it without being weird? Continue reading

Podcast Ep.119 – How to deal with dating flakey people?


Dating flakey people really are the worst. Unreliable, infuriating, and inconsiderate. The problem is, we can’t completely avoid people flaking on us at least once. So how do you deal with dating flakey people? I know you’ve been wondering, so we’ve got some answers for you.

We get into why people flake before dates, what it’s like to be in relationship with a flakey person, and what you can do to work through flakey behavior is a partner. PLUS: Live tweeting your own funeral, why flaking really sucks if you take the subway, and we get very specific about bygone New York cultural institutions and the best way to eat a Jamaican beef patty.

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If you enjoyed this episode you can subscribe to the podcast on iTunesStitcher, or Google Play Music.

Good Luck Out There.

Intro song: Slow Down by Ryan Little
Intermission song: Dirt Rhodes by Kevin MacLeod

Any advice for loosening up on a first date?


siguelacumbia asks:

Any advice for loosening up on a first date and being less serious and non-talkative?

I have a habit of being very serious and not jokey and very short in responses and not talkative when I feel uncomfortable.
I’m going on a first date with a girl tomorrow which makes me feel a bit uncomfortable, so I’m worried I may fuck it up in that way.
Any advice? Is downing just one shot beforehand a bad idea? Continue reading

Let’s prep for your online date!


Whether you’re trying out online dating for the first time, or an old pro who needs a little advice about prepping for first dates. First dates, no matter how many you’ve been on, are no picnic. Getting someone to hold a conversation with you, getting to know them, building a rapport and finally, getting to the date planning stage are already pretty exhausting, and then to actually put in the work to get a first date on the calendar? It ain’t always easy.

So, with that in mind, I wanted to write this guide for you. I’ll break it into 3 sections:

  • Pre-Planning
  • Planning
  • Execution

Continue reading

Podcast Ep.118 – Should you tell them you’ve met someone else?


We’re back, did you miss us? For the first episode of 2017 we wanted to answer a question: If you’re dating someone, and you met someone else, when you end things, should you tell them you’ve met someone else?

Seems like a simple enough question, so we wanted to dig a little deeper. How serious do you need to be? How honest do you need to be? Should you just never tell someone why you want to end things. We get into all that, plus a great boiler plate breakup message that would probably work well in greeting cards, and how cool it would be to have break-ups handled by an officiant.

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If you enjoyed this episode you can subscribe to the podcast on iTunesStitcher, or Google Play Music.

Good Luck Out There.

Intro song: Balboa by Jonas78
Intermission song: Ric Flair 2 by BenJamin Banger

Is a long distance relationship worth it?


DinoSorceress11h asks:

I’ve been home for the holidays (I go to school about 2000 km away from home) and met a guy (on tinder) we ended up hitting it off really well, and have gone on several dates over the past 2 weeks, and I think we both feel really comfortable with each other. The problem is that I fly back for school this Saturday and won’t be home again for at least 2 months. Is a long distance relationship possible when you’ve only known each other for such a short period of time? I really don’t want to lose touch with this guy but I know it’s probably unrealistic to expect a long distance relationship with someone who I’ve only known for less than 3 weeks
Would love to hear anyones thoughts/advice on this! Continue reading

Why is dating so complicated?


heartofgold29h asks:

I am a 24-year-old woman, and it seems the older I get, the worse dating becomes. Meaning, when I was 18-19 I didn’t really worry. I figured guys were just immature teenagers and in a few years it would be different. But now, years later, things aren’t much better. Most guys I meet would rather date around and not focus on one girl. It just gets frustrating and I get lonely. And it scares me to think that 10 years from now I could still be dealing with the frustrations from dating. Continue reading

Podcast Ep. 117 – How to Survive being Single over the Holidays


The holidays can be a tough time for a lot of people, especially single people, even if they don’t particularly celebrate any holidays. It’s a time of the year that is perfectly suited for couples, but singles, not so much.  For many single folks out there, the holidays can represent a period of intense stress, and intense isolation.

Whether it’s questions from family and friends that all really boil down to “why are you still single” or just feeling a general sense of loneliness, it can be a tough time for a lot of people out there. I’ve been single for quite a few holiday seasons and let me tell you, it can be hard, even for me.

But don’t worry though, I’m here to help. Let’s talk about how to survive being single over the holidays.

Press Play:


If you enjoyed this episode you can subscribe to the podcast on iTunesStitcher, or Google Play Music.

Good Luck Out There.

Intro song: Who Gosh by Big Mean Sound Machine
Intermission song:Sofa Christmas Jingle (ID 372) by Lobo Loco

p.s. I couldn’t find one specific resource for volunteering to spend time with elderly BUT, if you do a quick search for “Friendly visitor/visiting program” and add whatever city you live in, you’ll find a ton of resources.

Dating has made me miserable. What do I do to get over it?


 jaws4rl asks: 

First off a little background: I’ve never managed to get a successful relationship with a woman and every time I thought I would finally feel wanted by someone It turns out they were just using me/jerking me around. This was what I dealt with in High School and it made me not even want to risk getting emotionally or even physically involved with any women since I thought they would just treat me the same way I was treated in High School. I have major trust issues because of this and thanks to recent events they’ve only gotten worse. Fast forward six and a half years, I finally take down the emotional barriers with this female coworker and I think things will finally work out. Now I won’t lie and say I didn’t do my fair share of things wrong here but the way things turned out honestly may have destroyed the little trust I had in women. Short version, I told her I liked her, she said she didn’t want to date a coworker, I get a new job, she goes and dates someone else. Was a stupid for not just moving on at the initial rejection? Yes, and if I could I would have made a different decision at that point.

Since then I’ve been giving the online dating thing a shot but nothing has panned out. All I’ve gotten are half-hearted replies or women who “fade” on me right when things seem to be going good. I hate to be one of those guys but I have to wonder, maybe I’m just meant to be miserable. I don’t know maybe I just need someone to talk to about all of this (a female’s perspective might really help to be honest). I don’t like having animosity for a gender for something that not even 1% of them put me through but I guess when you’ve dealt with this betrayal for so many years this is how someone will react.

Maybe I’m just fucked up, maybe I need therapy, maybe I’m actually worthless. But when you go through High School hearing people say “you suck you suck you’ll be alone forever no matter what.” That kind of shit will end up sticking you know? I’ve kept all this bottled up inside for so many years and now I don’t know what to do. Continue reading

Podcast Ep.116 – Should you Move In together?

So, you’ve been dating each other for a while now, your relationship is progressing, and now you’re thinking that maybe it’s time to think about moving in together. The question is, should you? Should you move in together? Should you make that next big step together? Don’t have the answer? Well don’t worry, we’re here to help.

We get into what it takes to make moving in with someone work, whether or not a couple can have a life together while living apart, some reasons you shouldn’t move in together and more. Plus, we shout out a fan who sent over some love, and we make an addendum to an earlier episode based on some constructive listener feedback.

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If you enjoyed this episode you can subscribe to the podcast on iTunesStitcher, or Google Play Music.

Good Luck Out There.

Intro song: Dumbo gets drunk by 23 And Beyond The Infinite
Intermission song: Call One by 23 And Beyond The Infinite