Should I Date A Player Even When I Know He’s Going to Be Trouble?

I am single, early 50’s and live in a small town. I have been friends with a man whose marriage has been unraveling for some time, and his wife recently moved out. Divorce proceedings have begun. His wife is questioning her own sexuality and thinks she may be bisexual (this is her third failed marriage.) He is (was?) rumoured to be having a sexual relationship with an older married woman in town. (Sound like Peyton Place yet?)   I never ask, but he denies the affair, insists they are just friends & the rumour was started by his wife’s new lesbian friend, who is quite a gossip. At town functions, he sometimes hangs out with the older woman and her husband and kids like nothing is going on.

Our “friendship” has clearly changed and there is a great deal of flirting, texting, dropping by, spending more time together, and I am becoming interested in him… We have a lot of laughs and get along well. He asked me to dinner & I made a lame excuse, he told me to tell him when I am ready…something tells me I am entering a hornet’s nest and something else tells me if I don’t go for it, I will lose my window of opportunity & someone else will snatch him up and I will be kicking myself. What to do? Thank you.
Anne

Dear Anne,

Thank you for asking such an important question. However, without more information about your “friend,” it becomes next to impossible to give you a solid answer. You tell me he’s a player, but all I know is that he’s been married for years and is rumored to be having an affair. That’s not much to go on, and it’s certainly not my place to tag him a player based on conjecture and the small-town rumor mill.

So, because I don’t know anything about him, I’m going to use your email as a leaping-off point to talk about actual “players.” In fact, this week, I wrote a newsletter about this very topic (and if you’re not on my free newsletter list, you’re missing out — my most thoughtful material — plus discounts on my products – are reserved for my newsletter).

Anyway, in that email, entitled “You Don’t Want Him Anyway,” I told the story of a client named Alice, who recently fell for a player and had her heart broken.

With players — the end result is always so predictable that, frankly, it’s a bit of a cliché.

He was cute, charismatic, on the rebound, and interested — until he immediately pulled away from Alice after they slept together. In fact, the only thing different between you and Alice, Anne, is that you haven’t slept with your friend yet.

Ready for Lasting Love?
Ready for Lasting Love?

And that’s the sad thing about women who are attracted to players — the end result is always so predictable that, frankly, it’s a bit of a cliché.

Since I like to be logical about dating, let’s think about a player in terms of risk/reward.

What do you gain from dating the player? Well, think about it: you gain a rush of pleasure — serotonin, dopamine, endorphins. Aaaaand, come to think of it, that’s about it.

Because if you look at your history with players, you never get anything else out of them.

I think that players have a less than 5% chance of committing to anyone in the long run.

Consistency? No.
Security? No.
Kindness? No.
Unconditional love? No.
Future? No.

Players — and I know, since I’ve been one — are thinking purely of their selfish need to conquer new women. They don’t want to hurt you, but, hey, all’s fair in love and war.

I would say that there are 3 type of players.

Type 1: The players who pull a Houdini after the first time you sleep together. Frankly, the “fuck and run” is plain just bad etiquette, but it doesn’t matter to this player, because, well, he’s never going to talk to you again.

Type 2: The players who do the “slow fade.” In this instance, he cools off after a few weeks together and suddenly becomes unavailable for plans. A few weeks later, he exits, silently, without any fanfare or real explanation. He didn’t want to be the Type 1 player, but didn’t want to commit to you either.

Type 3: The players who let you think that you have a chance at being their girlfriend but have absolutely no intention of being your boyfriend. These guys follow up just enough to keep your misplaced faith alive. Next thing you know, he’s “the guy you’re seeing,” and he texts you a couple times a week, but almost never proposes dinner, weekends away, or phone conversations to talk. He is USING YOU and you are PUTTING UP WITH IT. All because he MIGHT step up to the plate and become your boyfriend.

So now let’s evaluate the odds of the player becoming your boyfriend.

The player is charming. The player is attractive. The player is interesting. The player is desired by many women. The player has a healthy ego. The player is always looking for the next challenge. This is what MAKES him a player.

Which is to say that NOBODY gets the player until he has decided (like I did at age 35) that I was ready to stop playing.

DO YOU WANT TO FIX YOUR BROKEN MAN-PICKER?

You think the guy who’s fresh out of a divorce is ready to stop playing, Anne?

I don’t.

I think that players have a less than 5% chance of committing to anyone in the long run.

Look at your history. I’d think you’d agree.

Would you board an airplane that only landed 5% of the time? I wouldn’t.

So to your point: “Something tells me I am entering a hornet’s nest and something else tells me if I don’t go for it, I will lose my window of opportunity & someone else will snatch him up and I will be kicking myself.”

Yes, you are entering a hornet’s nest.

Yes, you will lose your window of opportunity.

But you won’t be kicking yourself, because your player will soon become someone ELSE’S problem.

Just don’t let him become yours.

And if you’re not on my free newsletter list, you’re missing out! My most thoughtful material — plus discounts on my products — are reserved for my newsletter.

DO YOU WANT TO FIX YOUR BROKEN MAN-PICKER?