When you play not to lose, you’ll lose — even when it comes to dating.

Yeah, she’s over it bro.

Recently a woman I was dating stopped seeing me because: “I don’t want to be your Wednesday girl.”

And I was like, “baby I’m not a player I just crush a lot.”


No in all seriousness, I told her the truth: she wasn’t my Wednesday girl.

Because there was no Wednesday girl. Nor a Tuesday girl. Nor a Thursday girl.

The sad truth is kids, I didn’t even have a Saturday girl at the time.

No, I was actually at the time completely single and not dating anyone. Granted, this is rare for me, and I don’t believe in monogamous dating (let’s not be ridiculous — and I’m not opposed to monogamy necessarily, but there has to be a conversation at some point), but it was odd to be accused of being a player when I was playing by myse—

OK, bad analogy.

But it’s not the first time I’ve had a woman get scared as soon as she starts getting the feelz to the point where she torches our association after only a few dates.

Granted, it could be this was the excuse these ladies gave when there was some other reason they didn’t want to explain. Perhaps.

But all anyone can do is observe objectively what is happening and assume it’s real (#existentialism for the win), in which case, everything to this point was clicking: conversation, chemistry… copulation. In other words, if the women who’ve gotten the yips with me weren’t genuinely interested, they did a damn poor job of conveying that fact.

Like, as Shakira famously noted: the hips don’t lie.

Anyway, I’m making light of the situation because it’s that or be terribly depressed. Cause it’s a tragedy. It really is. To kill that magic spark — that romantic connection — before it even has a chance to catch fire? DAMN that sucks…

It reminds me of something we see play out in so often in sports: one team dominates the other, builds a big lead — but at some point the strategy shifts. Instead of playing to win, they start playing not to lose, as if more concerned about the hypothetical criticism of the Monday morning quarterbacks than beating the other team in the present moment, and playing conservatively somehow becomes the goal instead of winning the goddamn game.

And we all know what happens next: the other team, desperate, seizing the aggression, makes a tremendous comeback, beating the team who had the lead and by all accounts should have won.

Why? Because they’re no longer using the same tactics and strategies that helped them get ahead in the first place.

Instead they hold the ball — in dating: they stop texting back with regularity or limit the number of dates; they institute false timelines and schedules.

They focus on defense — in dating: restraining communication and physical contact; trying to set expectations for the relationship without explaining directly what it is that they want.

They stop trying to score — in dating: make out sessions and/or sex become more infrequent or stop happening entirely.

And what’s even crazier is sometimes people just forfeit. It’s like they’re ahead two touchdowns and just say, ya know, enough of this winning — I’d like to lose now, thanks.

I suppose I should define what I mean by win/lose. Obviously in sports, at the end of the game one team wins and other team loses (unless it’s soccer or hockey I suppose).

But relationships don’t work that way.

No, in relationships, either both people lose or both people win. Obviously a loss is when one or both parties break it off, along with certain associated feelings of disappointment, loss, sadness, regret, guilt, etc.

Winning is more complicated and depends on the goals for each individual.

A conventional win means the relationship ends with an expensive ring, a white dress, and a walk down the aisle; on the flip side it could simply mean dating non-exclusively and enjoying each other’s company as part of a polyamorous relationship. Again, everyone’s different and that’s a conversation that has to happen.

But when someone decides not to play when the start of the relationship is good — i.e. you’re both winning — it’s like… wait, WHAT? You do realize we’re winning here right? That all we have to do is keep going on dates and having great conversations and companionship and really great s —

Snuggles. Cuddles?


But in dating, like sports, when we play not to lose, we’re almost certainly going to lose. I’ve heard so many people say as an excuse (in my case, women): “I don’t want to get hurt.”

Well guess what darlin? I don’t want to get hurt either! But that’s a possibility, because we all know you could suddenly decide dating isn’t a priority at this time. Or move for a job. Or reconnect with an ex. Or ghost me for whatever reason. Or walk out the door any moment and get crazy with my next door neighbor you matched with on Bumble.


But here’s the thing: if we have something cool going, I’m willing to take the risk. I’m willing to acknowledge that our relationship is voluntary and that either of us can leave or ask to change the terms at anytime. And yeah, a lot of times it won’t work — hell, a lot of marriages don’t work, even though no one ever gets married expecting a divorce.

Anyway, if you want to win — whatever that means — you have to play the game, and that means accepting that you might lose. And if you are playing, holy shit: don’t quit when you’re kicking ass!

The other thing is that even if you lose — even if you don’t end up getting married and living that perfect Instagram life together happily ever after — chances are you had some great times. And that in itself is worth something, isn’t it?

Plus, and this is key: human beings are anti-fragile. What doesn’t kill us makes us stronger. And so, though it may suck for awhile, the inevitable truth is that you will find a way to heal, get back on your feet, and live to love again.

Note that this does not apply when there’s no connection, no passion, no spark. In that case I get it: ABORT, PRIVATE, ABORT! And for someone who’s experienced some kind of recent heartbreaking loss or relationship trauma, it’s probably best not to date until you’ve healed, because as anyone in the game can tell you, it’s rough out there.

But if the connection is real, the chemistry is hot, and you’re getting the feelz… well, isn’t that the whole point?

Jeff Allen is an independent author and blogger living in Portland, OR. His website is ChuckingRocks.com, where he writes about Health and Fitness, Dating, Existentialism, and Social Commentary. You can find a few of his short stories there as well.

His first novel, Cherry City Pulp, is darkly comic take on modern American society and what happens when coincidence and human frailty break the wrong way.

His new novel, Say Yes, debuts in 2019.