An Inside Look Into How Men REALLY Use OKCupid

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Hi, I’m Will.

So I’m a guy. And I enjoy talking about relationships more than most folks. I’ve been recovering as a socially awkward person for as long as I can remember. I figured out that one of the secrets to life, like dating, is to try something and fail miserably. And if that doesn’t work, try again!

I like to share stories of my time out in the “wilderness” aka dating. That, and I can give the ‘guy’ opinion on female related dating topics. Not to worry, I have the snarky personality to back it all up. I was even a dating coach once for a short time. I’m not a dating expert by any means, but I do know enough to be dangerous.

Also, to my future partner, if you are reading this, I don’t mind talking about it. I think it’s a great conversation piece.

So without further ado, my first article will be about…OkCupid.

OkCupid is a very interesting beast.

Most of my young single friends have OkCupid profiles. But it’s like a huge secret, we don’t talk about it. We may even see someone we know searching through profiles, but it’s pretty much like we don’t see them. It’s a guilty pleasure for myself and my colleagues. However, what I find interesting is what people do with said online dating profile.

First, there are my female friends. I have plenty of successful and attractive ones in my social circles. Most of the conversation revolves around a few topics. One being openly mocking the horrendous attempts of guys talking with them online. Most of the messages are rude, lewd and downright inappropriate. They usually trade inappropriate pictures or messages amongst themselves, while categorically denying that they are even on the website. Even worse, when one of my female friends does decide to meet a date in person, they always come back disappointed. They tell stories of bad mannerisms and out-of-line expectations. I know it’s pretty much unfair to women online. They are bombarded with messages, and it’s kind of hard to sift through what’s real and authentic.

Then there are my male friends. We don’t talk about OkCupid much between ourselves, minus those rare ‘bro’ moments where we complain about women. However, where most of the conversation is fluff, I have known guys who are obsessed with how it all works. They send hundreds of messages, they have systems for responses, and they always seem to focus on some minute flaw or detail as means of disqualification. Also, on the response front, they are usually surprised when they don’t get the response they are looking for, especially with their ‘generous offer’ of companionship. *cough*

Then there is me. Being a geek, I like to apply metrics to my life. How many girls am I talking to? How many responded? What can I do to improve my results? I like to get the best bang for my buck, and OkCupid is a great playground to play in. I know that makes me somewhat hypocritical, and I’m okay with that. I also know that sadly, the “best of breed” girls, the “Perfect 10’s” of the world more than likely does not have a OkCupid profile. I do not see the girls  at the Merchandise Mart dressed to the nines checking their phones for guys on OkCupid. This is not say I don’t have standards, but I’m not naive either.


So here is what goes through my head.

On my profile (if you can find it, that is), I know that I have to differentiate myself somehow. So, I hired a copywriter to write my profile. Someone who is an expert in telling stories and convincing people to engage. I was authentic as possible, almost to a fault. To this day, I don’t have to change it much, other than current activities. Then there are photos. I make sure to have photos of me doing interesting things, and surrounded by friends as well.

Then of course, what am I looking for? Well, therein lies the problem. Due to the advent of Catfish (note: for those unfamiliar with the term, look up Manti Te’o), spam bots who want you to send them money to their online sex chat rooms, and just people in general who embellish their profiles to a point, I don’t really believe much I see online. Regardless, I do have some deal breakers. I always look for profiles that have full body shots. I don’t care about weight necessarily, but if you are insecure about the way you look, the effect usually magnifies in person. Then of course, I read her profile, and I can’t tell you how many times I read ‘directives’ or ‘things I must do, say or be’ in order to date said person. The problem is that it gives me a vibe that she will be very controlling and jealous, which is also usually a bigger problem.

Of course, like anything in life, these aren’t hard and fast rules. Because of the ubiquitous nature of the profiles on the site, it’s usually a quick glance, and I decide if I’m going to send a message to her. (By the way, no matter what anyone tells you, guys are still expected to initiate the conversation. And no, views, likes, flirts or any other ‘letting you know I’m here’ type tactics NEVER work. Pony up and say hi to her.)

So, what to say to her? My tactic is to be short, sweet, simple and to the point. Read her profile, bring up some fact or thing that says you are paying attention and send it to her. Brevity is the soul of wit. But most importantly, remove all references to sex, relationships, future plans, etc. Again, you don’t know who she is. And she could be lying to you. And most of the time, you’ll be different from most of the guys sending messages to her. Remember my female friends? I take cues from their discussions.

Conversation is going well? Fantastic. Here’s the next part, meeting her in real life. I try to get the conversation offline as fast as possible. There is no set limit on the number of messages, but I always keep in mind to not let the back and forth go on forever. I did have an almost 2 month conversation on OkCupid with someone before I met them, but that was a special case. (As an aside: Be safe when dealing with folks online. Don’t give out your personal identifying information. Get a Google Voice number. I’ve had to block some people in my travels.)

In going for the offline meetup, I have one simple suggestion. Coffee. In a public place, equidistant from your place to hers.

Why? For a number of reasons. Rule #1: The first date is not the first date. Rule #2: THE FIRST DATE IS NOT THE FIRST DATE.

This is the time to get to know her, as if you were going to meet her at a party and ask for her phone number.  Other benefits include:

  • No pressure. Show up in your jeans with your hair messed up.
  • Saves you both time and money. It’s only 15 minutes, and it’s only coffee.
  • You can learn much more about her in real life than you ever would online.

I advocate this because I have too many friends who ‘overcommit’ on the first time they meet someone from OkCupid. They invest so much time and energy into someone they don’t know. You wouldn’t hire someone for a job, sight unseen without meeting them in person first, right? Same rule applies here. Besides, if you are tactical, you already have the real ‘First Date’ (The NCAA would call this the Second Round) already planned out, and you ask her to join you later. Even that evening in some cases if it pans out. From this point, it’s up to you. Dating is always about the adventure!

Last and certainly not least, I leave you with this. Don’t take it personal. I try to not attach any real meaning to my conversations online. I say this because like dating in real life, people are finicky creatures. Every rejection, while it hurts in the short-term is not your destiny. I always say ‘You got off lucky. No children were born, and no life-altering disease was spread!’ I always have viewed OkCupid as a fun thing to do when you are bored. And also, it’s no substitute for having a kick-ass life with all of your friends.

P.S If you want to see some extreme examples of OkCupid, check out an article about Chris McKinlay, who used math to find his next girlfriend.  And for even more laughs? Check out Tim Ferris and his use of virtual assistants to help him find his.

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