How I Learned to Stop Worrying and Love OkCupid

How I Learned to Stop Worrying and Love OkCupid


Like many in my generation, I’ve begun the search for some kind of playmate using the online dating platform, OkCupid. I say “playmate” because I’m still unsure exactly what it is I’m looking for. With the exception of junior high and the early part of high school, I’ve spent most of my romantic life in long-term relationships. I’ve had my share of flings, kisses with strangers, even a one-night stand, but mostly I’m a relationship girl. That being said, I’ve never been good at the whole monogamy thing. I’ve gone through spurts of loyalty (years-long spurts, even) muddied by occasional moments of infidelity. Usually, rupturing the monogamy bubble is a sign that I’m ready to end a relationship, though I tend to carry these things out much longer than I should. I’ve always been adept at ripping off real Band-Aids, but the proverbial ones give me trouble.

I’m also not sure what kind of person/people I’m looking for. I’ve had long-term relationships with both men and women, dated people my own age and dated someone older than my stepdad. (Daddy issues, holla!) When you’re not sure what/who you want, it makes dating especially hard. You see someone’s profile declaring that they’re looking for “short-term relationships” or, purely hypothetical obvz, a guy you’ve known for years sends you a Facebook message asking to hang out despite the fact that he is on the road for work the majority of the time (and is in the process of relocating to the other side of the country, ftw) and it’s almost insulting, like “Oh, so you think I’m the kind of girl you can just have a fling with? I’m not relationship material, HMMMM?!?” But then really, maybe a casual thing is all you want anyway?

On the other end of the spectrum, there are the guys and gals looking to settle down. The ones who want babies and marriage (even of the gay variety, since it’s totes about to be legal in my home state in a few weeks) and—ha ha ha, yeah right, those people aren’t on OKCupid. They’re probably all on Christian Mingle. Or they’re old enough to have fathered/mothered you. To be honest, these people terrify me because they threaten my personal freedom. When I’m initially single, I go through a brief period of mourning for the loss of my relationship comfort and security, but then BOOM, I start to become a way better version of myself. At least I’d like to think so. Being single is a great motivator to tap into creative outlets, go on new adventures, and drop weight so fast people start to accuse you of having an eating disorder. It’s. Awesome.

So why would I join a dating website if I’m not sure what I want? Well, they say you find love when you’re not looking. I’m totally not looking for that, I’m just looking for new experiences and new people to have fun with. If I come across someone who challenges me to be even better than my single self, that’s rad. If not, at least the experiences make good stories! Now that I’ve been on a few dates with OkCupid folk, I have some general Dos and Don’ts for how to approach free online dating:

  1. Don’t take it too seriously. The thing is, OKC is a free website. This means you’re going to get all kinds. Part of being on this website (or similar, free dating websites) is accepting that you’re not finding what you want in person and being humble enough to try something else. However, if you are looking to find a special someone ASAP, I recommend joining a pay site. Free websites mean a lot of people just looking for easy hookups.
  2. Do limit your use. When talking to a friend recently about starting a profile of her own, I warned her that if she’s not careful, joining OKC can be a big timesuck. I swear I lost four days of my life trying to develop a profile, answer questions, and respond to messages. After my four-day binge, I was left feeling like I needed the longest shower in the world. Seriously, if you take the time to read every message, scrutinize every profile, and agonize over every word in your own profile, you are going to be miserable. Plus, the more time you spend trolling dudes/chicks, the higher likelihood you’ll “run into” someone you know. In the first week I joined the site, I saw profiles for two people I knew IRL and was messaged by a RL acquaintance. If you want to avoid potential awkwardness and/or skin crawling feelings of blechgross, it’s best to spend only as much time as you need to exchange numbers or e-mails with a few people who pique your interest.
  3. Don’t underestimate yourself. One thing about online dating is that people take time to present themselves a certain way. You’re not the only one who used an online thesaurus to select adjectives for the “about me” section, okay? That means no matter how intimidatingly and amazingly awesome someone seems on screen, they’re still (probably) human and thus have flaws. On Friday I’m going on a date with a SOCIAL JUSTICE LAWYER who BIKE COMMUTES YEAR ROUND and I spent my Tuesday night drinking white wine spritzers and watching Bravo. Even if it goes nowhere, I am refusing to allow my insecurities to put the kibosh on a potentially fun evening.
  4. Do say yes to real life meet-ups. I don’t mean you should be indiscriminate when selecting potential dates but if someone doesn’t give you the total creep vibe and you’ve been able to bond over some commonality, it’s best to test out your compatibility in person early on. Even if there’s no chemistry, going out on dates is a great way to try new things while finding out what you are (or are not) looking for. Plus, do you really want to waste weeks or months of your time flirting with someone only to find out that you don’t click in person?
  5. Don’t go to their home/invite them to your home the first time you meet. I’d like to say this is a no-brainer, but a friend of mine who shall remain nameless has done this more than once. She’s lucky nothing has ever gone wrong, but you might not be as lucky. Besides, even if you just want to hookup, you’re better off meeting in a public place first. That way, if you find you’re not attracted to them, there’s not a bed in the corner creating awkward pressure. Of course, even if you do end up alone together, you should never feel pressured to do more than you’re comfortable doing. No means no, y’all!
  6. Do tell your friends about it. This one should also be a no-brainer, but I think sometimes people get self-conscious and thus shy about the fact that they’ve turned to the *GASP* internet (!!!) for romance. Swallow your pride and get over it. Lots of people (TONS of people) have found success this way, and even if you don’t, your friends should be cool with it. If they’re not, you need new friends. One reason you should tell your friends is that even though it’s pretty darn safe, there’s still that whole Craigslist killer or Catfish fear looming in the back of your head. If it’s not, maybe it should be. If your friends know where you’re going, or better yet, if you make plans to meet up with your friends after the date, you’ve got yourself a built in safety net.

Good luck and remember, dating profiles are temporary but herpes lasts forever…wrap it up!

– Stephanie Ann