The Art of Ass-Kicking: 6 Thoughts on Online Dating from a Guy’s Perspective

Okay.  I know I promised to get back to writing my own blog but when I made that promise, I’d forgotten that I’d signed up for a blog swap over at 20 Something Bloggers.  So we’ve got another guest post for today written by Jason Shen but rest assured: the Pittsburgh Saga will continue, first thing tomorrow.  Also, you can check out my post for today over at Jason’s blog: The Art of Ass Kicking

Ass KickingHey guys – I’m Jason! I’m a twenty-something guy who grew up on near Boston, went to school in California (Stanford) and now live in San Francisco.

I write a blog called The Art of Ass-Kicking which means I mostly blog about things like taking cold showers, lessons learned from working at a startup, and getting personally rejected 30 days straight.

One topic that doesn’t get much coverage is my dating life (surprise, surprise). Which makes it great that I’ve been partnered here with Kat for this blog swap.

I’m a big fan of online dating (as the co-founder of an Internet startup, I find that it’s the only thing that gets me out of the house and meeting people) and I know Kat has some experience with it too.

There’s definitely some big differences (in my mind) about about online dating from the male vs female perspective– and perhaps from the East Coast and the West Coast. So without further ado, here are six thoughts from me on online dating– Some of these are lessons, some are questions some are just observations. Enjoy!

internet dating image

Don’t message too much before the first date.

I went on several dates with a girl I met on OkCupid (my dating site of choice) who was going to med school in UCSF; we’ll call her Jane. I read Jane’s profile carefully- she seemed smart, cute and we shared a similar upbringing. I sent her a carefully-worded message which lead to a seven or 8eightmessage thread, each multiple paragraphs long.

We had a lot to share and I was excited to read each of her messages. This was great fun, except that it meant that by the time we got to our first date  we had already exhausted so much of what would typically be “first date” conversation.

There was no sense of surprise or discovery and a few dates later, I called it off with Jane. If someone seems interesting, don’t build up a dossier on them, just go on a freaking date!

How does “spray-and-pray” messaging work?

The point about not messaging each other too much leads me to this next thought: what about the reverse? It seems like the dominant strategy on dating sites (for guys at least) is to send a ton of short, impersonal messages like “hey cutie, what’s up” or something. How do I know this? Because tons of girls have gotten so many messages that they explicitly state things like:

“I’m definitely not responding to you if  send me a one-line message. SO PLEASE STOP SENDING THEM. THANKS.”

Apparently there is even a blog dedicated to strange (and usually short) OkCupid messages: This is not Ok, Cupid. I’m sure none of this stops “spray-and-pray” guys from charging ahead. But the thing is, I don’t think they’d do this unless it worked at least some of the time, which I kind of find amazing.

So if anyone has used this tactic successfully – please email me and share your wisdom! jasonyshen[at]gmail[.]com. Thanks!

Apparently girls message more on the East Coast?

I have a roommate who lived in Pittsburgh for 10 years. (That’s pretty close to Philadelphia right?) Anyway, he’s used extensively OkCupid to get dates / girlfriends and he found the most luck with a passive approach. He started off messaging girls  lot with little to show for it. After a while he just gave up and got much more passive – viewing profiles from time to time but not messaging. Amazingly, girls began to message him! His last two girlfriends were girls that had messaged him out of the blue.

I don’t know how common his experience is but it seems like that would never work on the West Coast. We single men are already at a demographic disadvantage compared to single women (which is why I’m moving to New York when I get older), and online dating probably skews the ratio even further.

An alternative explanation is that it’s not a location thing but that my roommate is just really attractive and good at writing interesting profiles.

Embed hooks into your profile to pique interest.

One thing my roommate taught me was to embed hooks into my dating profile. So for instance, he’s participated in a run for charity that involved him wearing a cow suit. So in his profile he would write “And there’s this great story that ends with me running across a bridge in a cow suit. In fact, that would make a great message- why don’t you ask me ‘Hey – how did you end up in that cow suit?’ and I’ll tell you the whole story.”

I agree that the hook is a good idea, but what’s amazing is that some girls would literally just copy and paste his suggested message in and send it off – no editing. It goes to show that dating and marketing aren’t that different – you need a clear and actionable call to action. I implemented his advice on my own profile (with a story related to me, obviously) and have gotten at least a couple responses – so I guess it really does work. Give it a shot and let me know!

It’s amazing what people will publicly answer to on their profile.

One feature of OkCupid that I like a lot is the personality questions. There are tons of questions that have been created by users that you can answer – on dating (how do you deal with ex’s) or lifestyle (what’s more important, fame or money?). You pick from the multiple choice answers for yourself, then what your ideal partner would answer and how important this is to you.

If you’ve answered a lot of questions and overlap with a person you’re checking out, you can see what your “match percentage” is based on your respective answers to the questions. While you can hide your answers to the questions, most people don’t, so you can see people’s responses to things like:

“Would you dump your significant other if they were overweight” or “How much do you enjoy going down on your partner”. I’ve learned seemingly truthful things about random strangers that I probably don’t know about my close friends. Isn’t that wild?

It’s really weird to see people from OkCupid in real life/and vice versa.

Online dating is becoming a mainstream thing– apparently 1/6 marriages in 2010 were started online. Still, it’s kind of a hush hush thing and I’ve gone on several dates where the girl didn’t want her friends to know that we met online. But as more people get onto a service, it’ll get more accepted.

Still, I find it weird to see people I know in real life in my OkCupid match listings. It’s interesting to read their dating profile – kind of like reading a resume for their romantic aspirations.

What’s even more awkward was when I was introduced to this Indian girl named “Ashni” at a party. I thought she looked really familiar and I asked if we had met before. She said we hadn’t, but I wasn’t convinced.

It wasn’t until later in the evening when it clicked. I walked over to her and asked “Are you on OkCupid?”  She’s like “Yeah..” I was like “Are you lilmissindia77 (not her real screen name)?” and she was like “Yeah….” and blushed. Boy, that was an interesting moment. So yeah, online dating is going mainstream, but there’s still plenty of room for awkwardness.

S0 that’s what I got. I hope you enjoyed my six thoughts on online dating. If you liked my writing and want to read more hard core stuff about performing at your best and overcoming your fears, please check out my site: The Art of Ass-Kicking.

Most Valuable BloggerPS: Kat here again– I’ve been nominated for “Philadelphia’s Most Valuable Blogger” and I need your help!  You can vote for me everyday, once a day until September 9th (no login or registration nonsense required) so please click on “VOTE FOR ME” to cast your vote.  THANKS!

3 Responses to “The Art of Ass-Kicking: 6 Thoughts on Online Dating from a Guy’s Perspective”

  1. Zak


    Some really interesting thoughts, thanks! As for the “spray and pray” method, I think it works if you do it unlike all the other guys. Here’s my version.

    I really liked your advice on the hook, and if I was still doing online dating – as in, if I wasn’t the luckiest guy in the world! – I’d be all for giving that a try.

    Lastly, I’ve run into a few people from the online dating world. One I was talking to but never met, a few I’ve met but it didn’t go anywhere, and some in between. It is always awkward.

  2. Gund

    Is the graphic supposed to have the ‘F’ key replaced by a heart symbol?


    • Kat Richter

      I don’t get it. I’ve been baffled by the image ever since it was sent to me by this post’s author… I was hoping your comment might shed some light but I am still confused!


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