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.

How do I break up a friend’s toxic relationship?

Joe_titan25 asks:

A friend of mine is a terrible boyfriend who often commits non-consensual acts against his girlfriends. How can I break up that relationship for the sake of his poor girlfriend? (And as a bonus, how could I possibly date her myself, yet respectfully?) Continue reading

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