How do I make the most out of online dating?

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Today’s question(s) comes from a lovely reader of mine who wants to remain anonymous. While her questions are fairly common, the background behind them adds a bit of a twist. 

She has two questions: First, she wanted to know how to decide whether or not to go on a second date. Second, how do you make the most of online dating.

Before I answer those questions, a bit of background about her. She grew up in a conservative community, got engaged to her first boyfriend, narrowly escaped an emotionally abusive marriage, and is now learning how to date in the middle of a busy career. She broke off the engagement, but between that relationship and the several years it took to recover, she essentially missed out on the critical period when most young people learn how to date.


Demetrius says:

Let me just say that I don’t know you that well, but the fact that you’ve made strides to better your life and that you’re getting back out into dating while balancing a busy career is incredibly admirable. Even if you worked a minimum wage job, the fact that you left an emotionally abusive marriage is commendable on its own, as many people feel they can’t or wont do it. For that you have my utmost respect, whatever that’s worth. Enough lauding you though, let’s tackle your questions.

Let’s start with In most situation where you are trying to figure out whether or not a second date is in the cards, the date was good, but not great. The date was the Merriam Webster’s definition of “meh”As weird as it may sound, I actually decide whether or not I’m going to go on a second date with someone by trying to assign a certain value to the components of a date. I know it doesn’t sound like the most warm and fuzzy approach to dating, but just go with me on this. When I’m trying to figure out whether or not to go on a date, I try to assign value to the following factors:

  • Your time (Prep, Travel, Actual Date, etc.)
  • Cost (Prep, Cost of the Date, Cost of Travel, etc.)
  • Potential risks
  • Potential rewards
  • Should I be picky based on what I’m looking for?

Now, let’s say I’m in a hypothetical situation where I went on a less than stellar first date and I’m trying to figure out whether or not it’s worth it to go on a second  date. My total time for the first date was about 6 hours, I spent about $150 in total cost for the datemy potential risks would be offending her if I don’t ask for a third date (low risk),being hung over at work the next day if it’s a weekday date (medium), or I could just end up wasting a bunch of time and money (high), potential rewards are having a good time (low) having a great time (medium) having such a great time that I want a third date (high) and I probably should be picky because I’m looking for a relationship.

So now I’d ask myself if a 2nd date is worth spending 6 hours, $150 dollars, potentially risking wasting time and money because I wont want a third date, but it could lead to a 3rd date. Oh and I should be picky since I’m looking for a relationship. In this case, I probably wouldn’t go on a second date because the cost is prohibitive, the risks outweigh the rewards in my book, and while I’m sure this hypothetical woman is lovely, if I didn’t feel the spark on the first date, I don’t want to waste $150 dollars, 1/4th of a day, and risk a potential hangover to see if I read her wrong.

Now, it’s up to you to figure out what your time is worth, how much the cost of a date is worth to you, what your potential risks and rewards are, and if they’re worth it. If you’ve got a lot of free time, go on inexpensive dates, don’t think the risks are too high, and the rewards are pretty decent AND you’re okay not being picky because you’re aimlessly dating, go for it. If you don’t have a lot of free time, are concerned about the cost, feel as though the risks outweigh the rewards, and are picky, skip a second date. It’s been awhile since I went on two mediocre dates back to back and I regret it. I will say that depending on the gender/sexual orientation the values you assign to those 5 factors will change dramatically. I rarely if ever hear a lot of straight men say “The date was mediocre, but we’re going to go on a second date” mostly because men tend to emphasize cost (because they’re more likely to pay), where as you’re more likely to hear “He was okay, still not sure about him, but we’re going on a second date” from straight women because they tend to look at risks, rewards, and how important it is to be picky rather than the cost. The time thing really is more of an occupational thing, rather than a gendered/sexual orientation focus. People who work 10 hours or more a day are less likely to want to go on a potentially mediocre second date.

Now, as for making the most of online dating, I guess the main thing to look at is what you’re looking for first. If you were seeking casual sex, it takes pretty much zero effort on your part to make the most of online dating. Gear your profile toward casual sex, make it clear you’re seeking casual sex, and watch the matches/right swipes/dick pictures flood in. Assuming this isn’t the case, because I don’t think I’ve ever had a straight woman ask me how to get more casual sex because the demand for dicks is low, but the market is flooded, let’s tackle optimizing online dating for a busy professional who is open to dating and maybe a relationship.

First, ignore the idea that certain dating apps are for hookups. Yes, there are some apps that make hookups easier to facilitate and are used about 50% of the time for hookups, but they can also be used to facilitate dates just as easily. Dating apps are just tools. You can use a hammer to hammer in a nail, or take a nail out of a wall, right? Same goes for the Tumblecupid’s of the world. You can use {Insert Dating App/Website} for casual sex, casual dating, or long-term relationships, facilitating threesome, etc.  Another thing to note, you’ll get a lot of advice from peers that you should use a specific app for online dating, take that advice with a grain of salt. People’s experiences on dating apps are wholly unique to them, and depending on who you ask, their preferred dating app is the best, and it’s competitor is the worst. Yes, we all will encounter spam accounts, or vulgar people, but the potential individual matches and dates you’ll meet on any dating app will vary. I’ve never, ever, found a woman who only wanted to hookup on Tinder, but that’s just my experience. The way that people swear by Bumble or Tinder over other apps isn’t usually indicative of the quality of the apps themselves, but of the person’s experience using it. It’s why pretty much every single dating app out there that’s been around for 3+ years has a bunch of success stories they can share with users.Just google {Insert Dating App/Website} success story and you’ll see what I mean. Oh and despite what some people might believe, whether your picture or profile content are modest or not, as a woman who dates online you’re still going to either get harassed, receive vulgar messages, or just plain old copy pasted messages. It comes with the territory and even if you were wearing a nun’s habit in all your photos, specifically say that you don’t want anyone to reach out to you in a sex-seeking or vulgar way, you’re still at risk for a stray dick picture or insult in your inbox. You might get a little less of it than someone who only has bikini photos and a profile that says “My favorite flavor of popsicle is DICK”, but probably not as much as you’d think.

As for making the most of online dating, the first thing you should do if you aren’t already is to never respond to every message. Most of the messages you get will either consist of 1-3 words, an insult, copy pasta, are just plain rude. I’ve found that my experience on dating apps gets a bit better if I unmatch people I realize I never want to message or meet, or delete their message. You know how clutter can stress people out, dating app clutter can do the same, so get rid of it. Another thing that makes online dating much more enjoyable is turning off notifications. Seriously, just give it a shot, it will make you way less stressed out when you aren’t getting those “3000 people swiped right on you on Tinder in the last 15 minutes” notifications that you get. Most importantly, block rude people and don’t respond. You pretty much need to tailor your online dating experience in a way that it mirrors what you would or wouldn’t tolerate in real life. You should keep an open mind, but you don’t have to tolerate people’s shitty behavior just because you’re trying to date online.

You should fill out your profile using tidbits of information that will prompt conversations that you want to have. Love your job? Mention it in your profile. Hate your job? Don’t! Be sure to include pictures that look the way you look today, and include at least one picture where you think you look your best. Regardless of your body type, include a picture of your body. This picture will serve two major  purposes: First, it eliminates the potential matches who aren’t into your body type and second, it helps filter out the matches who are only looking for sex because they’ll only message you about your body. Include relevant info about yourself, but be wary of getting too specific. Some apps actually pull your job title, the company you work for, and your education history from either Facebook or LinkedIn, so be wary of that. With a first name, a title, where you went to school and where you work ,you can be found on the internet pretty quickly and if you work somewhere that’s unique, like a specific store/bar/etc., you risk having a rejected match show up where you work. Exercise caution above all else.

Don’t go on dates with people you’re on the fence about UNLESS you’ve got a lot of free time/money. If you’re busy, don’t waste your time on people who you’re on the fence about. You can be either specific or broad in your searches, but keep in mind that some sites are more suited for specificity than others. If you want to meet a nice Christian boy, who is above 6 feet tall, and doesn’t drink or smoke, you’d be better served by signing up for a dating website, rather than a dating app. Most dating apps only allow searches based on proximity and age, not height, religion, smoking preferences, etc. Don’t afraid to sign up for more niche sites if you feel like you’d be better served with even more specificity. Yes, you can find someone who is kinky on Match, but you’d have better luck on FetLife if that was your thing. Same goes less extreme niches like sites focused on dating for specific ethnicities, religions, groups, lifestyle choices and so on.

As for your past, I think it adds a bit of context for your jumping into the dating pool later in life, but I think once you know the basics of dating you’re not completely out of your element.  There are a few things you need to know if you’re fairly new to dating online: Online dating is widely accepted as a viable way to meet people, people are more inclined to casual dating now than they were 20 years ago, hookup culture is a big part of dating culture, and people seem to be more commitment averse. With all of that said, you don’t have to date that way if you don’t want to. Date the way you want to date. Yes, it will be harder for you to meet someone today who is looking to settle down (if that’s what you want) but it’s not impossible. Yes it’s harder to meet someone who will want to go on a real date and not “hang out” but it’s not impossible. You don’t have to bend your wants or ideals just because society is moving in one direction when it comes to dating and relationships. Date the way you want to, compromise if you want, but don’t be afraid to say “I want this, and I won’t date you if I can’t get it”. Don’t be afraid to look out for your own interests, especially when you’re investing time and money to date. Dating is an investment, and you should invest the way you want to.

My last piece of advice for getting the most out of dating is to not let the worst parts of dating get you down. There will be good, and there will be bad, and sometimes the bad outweighs the good, but you can’t let it get you down. Once you’re down on dating, it’s hard to be optimistic about anyone new who comes along with potential. You’ve overcome so much, and you can overcome all the worst parts of dating whether it’s someone you like ghosting you, not having time to meet someone, flakes, perverts, douchebags, and anything else life can throw at you. It’s not all sunshine and roses, but online dating can be worth it. As long as you date the way you want to.

Good Luck Out There.

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