When Dating Doesn’t Add Up

by Derek Hartley
Wednesday Jun 25, 2014

I’ve never been great at math, but I believe in it. Math took us to the moon, gave us the internet and keeps our bridges from falling down. So, I think it’s kind of important. Even in the abstract world of dating, math is useful. For example, you don’t need to take algebra to know that two bottoms don’t equal a top. In our age of science, math is at the heart of popular dating sites like, but there’s a lot more to romance than a simple algorithm.

I am on OKCupid and because I trust their technical underpinnings, I have answered more than 1500 of the questions in the database. When searching for a match, I am rigorous in my demand that they are at least 85% and I prefer an over 90% match. This is not how most people use the site. Generally, you look at the guys you are a high match with and after you don’t see anyone hot, you suddenly think you have more than enough in common with the 32% match with rippling abs. Here’s a hint: you don’t.

My highest match in the whole world is 97%. He’s even hot, a writer who used to be a professional dancer and lives near me too. My next highest match is 96% and he’s cute enough but lives in France so that doesn’t seem very practical at all. You would think, or at the very least, math would assume, my 97% match and I are nearly perfect for each other. But we are up against a bigger numbers problem than pure compatibility: age.

I am 44 and he is 36 and while there is a difference in age there, it’s not outrageous. We may not be in the same ballpark, but one of us is no further away than the front gate. However, a 36 year old is in a different place in life, with different options than a 44 year old.

This is a generalization, of course, because no matter what age you are, you will be constantly surprised by just who might throw themselves at you. For instance, it should warm the hearts of all 29 year olds everywhere sweating out their next birthday that when you are my age the ages of guys who will hit on you will range astonishingly from 19 to 69, in nearly equal numbers on both sides. All that aside, there is a correlation between your age and your willingness to settle down and no computer program in the world can predict exactly where it is.

Gay dating is a merry-go-round that never reveals the best time to get off it. If gay men make one gigantic mistake in dating, it’s the error of bad timing. They either get off too soon and end up sabotaging their relationships in favor of other sex with other people, or they wait too long and then are disappointed and upset by the choices they are left with when they do finally decide to settle down. Some people are simply settle-down people, and they’re the ones who marry their high school sweethearts and never look back. Others are still dancing in place with their shirt off for a record number of years in a row. Almost everyone else falls somewhere in between.

So what is the optimal age for getting off the merry-go-round and settling down? No one knows! It’s somewhere in the vast grey area between nearly falling down every time a hot guys jogs past you and refusing to date someone because you don’t like their furniture. Admittedly this is a wide gap, so for the sake of argument, we’ll say the average is sometime in your mid to late thirties.

In your early thirties, you are so besieged by young twenty-somethings who want to date and/or sleep with you, the prospect of settling down seems nonsensical, especially with a twenty-two year old. Even at 36, you still have the option of seemingly endless sexual encounters with hot but emotionally messed up guys in their late twenties, so why on earth would you want to seriously consider settling down with someone eight years older? I guess it all depends on how dedicated you are to settling down or how embarrassing it is to still be telling awkward Carrie Bradshaw-esque sex stories on the sunny side of forty.

Unfortunately, a dating site algorithm can’t process these numbers in a truly effective way. It can’t pinpoint the day when you meet a guy at a bar or a party or on the street and while he’s talking you no longer see the possibility of dating him. Instead you jump ahead through the next five steps, see in your mind how it will all end, and decide he isn’t worth the trouble. At 24, you can walk into almost any man’s apartment and picture yourself living there. But a few years later, the wrong paint color, pet, or iTunes playlist, will be an insurmountable deal breaker. You just know yourself too well.

For me, I don’t think I could date a guy who wears a lot of tank tops because I’m not really a sun and beach person and those are the kinds of guys who love a good tank top. And if he’s wearing a tank top and a scarf at the same time, not only do I not want to date him, I want to choke him out. My 97% match loves a good tank top, so I guess that’s in the 3% where we don’t match. Or maybe fundamental compatibility is a bridge that no amount of math can keep from falling down if both sides don’t want it to stay up.

Since 2003 Derek Hartley has been the host, along with Romaine Patterson, of the GLAAD Award-winning SiriusXM Radio show Derek and Romaine, emphasis on the "has been." The show airs weekdays from 8 to 11 p.m. ET, exclusively on SiriusXM OutQ 109, and is wildly inappropriate. Prior to joining SiriusXM, he was a columnist for PlanetOut. He is a major proponent of recycling, as evidenced by his two memoirs: Colonnade: A Life in Columns (Spacuna Publishing, 2009) and When Nightlife Falls (Spacuna Publishing, 2011). And he writes a semi-annual blog, entitled Initial Public Offerings, chronicling his nighttime adventures, because he is his own favorite subject. Obviously he is single and resides in New York.


  • Anonymous, 2014-07-03 07:53:39

    Derrick. Age is not the sole determining factor to find your "one". It is the spirit of the partners. I behave responsibly, but I have a very immature streak in me. My husband tries to be more mature than his years and he dresses a little older than his age. So, we have a GREAT marriage and we are 25 years different in age. (And, no, I’m not his "daddy". He takes care of me like a strong and confident husband should. I am happy to be his wife).

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