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.

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.

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.

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.

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  1. 1

    So true Evan.As a player myself. A player will only settle down when he’s ready.   Until then it’s all fun and games.   So proceed with caution.

  2. 2

    Evan is spot on as usual.

    Types 1 and 3 are very easy to identify very early own. Buys me one drink in a bar around the corner from his place and then invites me to check out the view? Next! Asks where I am going to be on a Saturday night instead of actually making plans with me? Next! Texts me 6 weeks after the first date saying he had lost his phone with my number (and I suppose with his password to his email account… )? Next!

    Problem is, Type 2 is very hard to figure out until its too late, i.e. the fade has began. I guess everyone who comes on too strong too early  is suspect, but you run the risk of penalizing a guy who actually is into you.

  3. 3

    Oh my gosh, Anne. The hornet’s nest feeling you’re experiencing is your mind’s way of screaming, “Get out now, while you still can!” Why would you kick yourself when some other “lucky” woman gets to inherit this man’s baggage? Let’s see, there’s a marriage that’s not legally over, a soon-to-be ex-wife whose sexual identity may be playing big time with his mind and heart, a rumored affair with a married woman with a family, and a man who’s on the rebound! Plus, you may also quickly becoming a juicy part of the town’s gossip!
    Here’s the thing ~ right now, the timing isn’t good. If the rumor isn’t true, then allowing for more time to pass will bring this revelation to light. Time will also give him the chance to clear his mind and heart, fully, and sign on the divorce decree before starting up a new relationship or dating. And if it should happen that another woman comes along and easily snatches him up in the meantime, while he’s basically trying to court you, well then what does that tell you? I am sure you’re wise enough to figure this one out.

  4. 4
    Christie Hartman, PhD

    I’ve got one word for you: REBOUND. As the expert on dating divorced men, I gotta tell you this guy is guaranteed trouble, at least right now. Newly separated, divorce just begun, wife with sexual identity issues, and god only knows the rest. Even if you put aside the “player” issue for a minute, you’re still looking at a high-risk relationship. Men in his situation are rarely ready to date despite their desire to, and the women who date them end up as my clients. It rarely turns out well.
    Stay his friend for now. If he’s a worthwhile guy, and there is anything worthwhile between you, the relationship has a better chance once he’s gotten divorced and dealt with his baggage.

  5. 5
    E. Foley

    If you’re looking for love, don’t date a player. As women, we always think that maybe WE’LL be so special that it’ll make him change his ways. You’re killing yourself with terminal uniqueness – you are not THAT special. No woman is. If he’s ready to settle down, he will. If he’s not, he’ll continue to play the field.
    Now, if there’s chemistry and you want something fun and no-strings, then go for it. Just don’t lose your heart.

  6. 6

    Wow.   Between Evan’s response & comments number 1 and 2, there’s  really not much I can add to that, except — and I say this as a woman in her 50s who’s been  invited more than once into the drama of younger men — IF YOU DO  give into the temptation and have a fling with this guy, don’t waste time kicking yourself later.    You’re human, and physical connection and the accompanying flattery  feels good, if you understand it for what it is.    The beauty of being 50+ is that  you  finally get it  that you really can’t control what  other people think of you (rumor mill) and it’s only important what YOU think of you.  Let them wag their tongues — it’s none of their frickin’ business.   But don’t share any of yourself with him  if it’s because you feel desperate, or “less than,”  or, heaven forbid, “lucky!” Based on what you’ve told us, my bet is that you are the catch, not him. You already recognize the potential hornet’s nest. So, even  if it  does turn out that you  miss that “window of opportunity,” not  to worry — I doubt  you’ll regret it for very long.   Take care, good luck!

  7. 7

    P.S.     I think many women are starting to  realize that The Player and The Bad Boy are way overrated.   Shallow, predictable  &, subsequently, boring.   Yawn.

  8. 8

    @ Zann #7

    I dunno about that..  As a single woman in New York I date pretty actively and I  would say out of 10 men who express interest in me  8 are classified as players immideately (type 1 or 3) and one turns out to be type 2. These are the stats. I kid you not, one of the guys actually tried to pull it on me twice (we first met a year ago and our paths crossed again), despite the fact that I told him outright to get lost the first time around. I find it very disturbing, because if he is consistently doing it, it means that his success rate is greater than zero. Sheesh! Women should really stop handing out “free” sex, this whole sexual freedom has totally corrupted men.

  9. 9

    It’s very simple. You play with fire, you gonna get burned sooner or later. And neither timing is pleasant.

    Separated / newly divorced men are – in general – to be avoided. There’s nothing but trouble ahead if you go down that path. Been there, done it myself. Ain’t gonna do it again….!

  10. 10

    @ Zann #5,
    Here here!!! You took the words right out of my, um, keyboard, as it were.   Players are interesting on the surface because they know how to charm women and make themselves appear to be more than they are.   But once a woman sees right through it, they’re boring and a dime a dozen.   It’s all well and good if you are looking for nothing but a good time.   However, if you want someone of quality, integrity, character, and depth, I’d not place my money on this one.

  11. 11
    Asian Internet Dating

    I think women get attracted to players for their charismatic personality and often they get entangled in their talks. At times it’s also more to have fun and self judgement on how good you can get along with such players. But on serious thinking, women should remain cautious on their relationships as it could hurt them later.

  12. 12

    Sounds to me like Christie put her finger on the true issue.   I don’t really see what makes this guy a player.   I do see what makes him a rebounder.

  13. 13

    Evan, this is somewhat of a sidebar to the original post and may be better addressed elsewhere.

    I’d like to know more about your statement that you decided to stop being a player at 35.  

    Did you  identify yourself a player  up until  then or just a guy unsucessfully  searching for Ms Right?

    Did it happen before or after meeting your lovely wife?

    Was this a conscious decision on your part or something you realised in retrospect?

    How did that decision manifest?   What changed in your thinking, behavior etc?

    I’m become more convinced that ‘readiness’ is a crucial factor in creating lasting relationships.   Timing is a crucial  factor.   You can meet someone very compatible with you but if both of you aren’t ready then it won’t take off.  

  14. 14
    Kat Wilder

    My take on it is this – if she’s just in it for the fun and the sex, why not? Many women who have a healthy sense of themselves and their sexuality can be “players,” too, without expectations of a relationship or happily-ever-after.
    But, if she does want the latter, steer clear. No one in the midst of a divorce, player or not, is ready to date again. Really. No one.

  15. 15

    When it comes to dating, our gut instincts are great indicators of what we are going to be letting ourselves into, but at the same time when you really want to be someone, it’s easy to push those feelings aside for a time and placate ourselevs, but eventually they resurface.

    So if you already sense and feel like he is a player – then you can take an educated guess as to what is available – if it matches what you are after then go for it. If not, let it go because at the end of the day, can you really lose something that was not even yours in the first place?

  16. 16

    So how does one identify a player before having sex with him? It seems that if they do everything right up until the point you sleep with them, you don’t really know. ..How many dates before the sex part?

  17. 17

    I agree with most everyone’s posts that the man in question is not a good “catch” right now, if maybe ever.   But Morgan’s post raises some good points.   Evan wrote, “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.”   In previous posts he has commended his wife for being very understanding with his flirtatious nature and giving him the benefit of the doubt when circumstances created a lot of doubt.
    So, at what point is it smart for a woman to run a way from a “player” because it probably won’t be conducive to long-term happiness and when should she try it and give him the benefit of the doubt?

  18. 18
    Sara Malamud

    If you are one of those women who love suffering or you are also a player, stay away. If by any chance you think ”he may change for me” forget it. They don’t change! what they change is women every week. Sara Malamud

  19. 19
    Sara Malamud

    Sorry i meant, unless you are a woman who loves suffering or you are also a player.

  20. 20

    I am a player of the #2 variety, used to be #3 until I outgrew that mode. My thing is, I almost always play the game with other *players*, that is, women who want to date around and who are also playing as much as I am. That’s the way it’s pretty aboveboard and we understand each other.

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