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.

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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.

  21. 21

    hello anne! if you can still escape with that kind of situation then out!please don’t let your heart hurt by someone who treat you as an option. . .that’s not worth of your time

  22. 22

    Depends on where he is in his life, you know his a player, why would you want to put yourself through that.

  23. 23

    My father once told me that a man isn’t a man until he learns to respect women. And that when a man disrespects a woman, he disrespects himself. So to me”players” are really just guys that might seem confident but underneath it all need external female validation that they are worthy enough to bei with. And once they are with these women, they can make themselves feel even better by choosing to toss these women to the side. It’s all about power, manipulation and self loathing with players. That’s why I’ve never been attracted to “players”.

  24. 24

    How enlightening…  Jersey Girl… I totally agree with your comments about respect/disrespect… So much good feedback by all! Evan thank you so much for what you are doing!
    Anne, I hope my story is of help to you….
    I was divorced a year ago after 12 years of marriage..(13 years together).He first introduced himself and pretended to be separated at first…  After learning this I told him to go take care of his marriage and GOODBYE! He came back months later saying he was in fact separated… and getting a divorce…and he hoped I see him!
    I had been divorced for 16 years thought I’d seen it all….But, I ended up braking my own rule about dating men who are separated… I’d generally say…no thanks….call me in year!
    However, I found myself falling for this seemingly wonderful man… I thought the same thing… if I don’t go with this…. someone else will catch this great guy!!  Everything he said and did… caused me to believe we were meant to be together… Thought he was unhappy and made some mistakes…but we were “special” together!!
    I began to see little bits of bad behavior…he’d apologize and say he was getting past some things etc…  Those little bits… slowly progressed over time and turned into abusive behavior… By the last year it was truly ugly!!  And of course… he repeated his infidelities… with me!
    A a narcissist he shows the world Mr. Wonderful..but he is actually the angry, insecure, manipulative, disrespectful and self loathing person behind the facade he portrays to keep others from seeing his own inadequacies…. I fell in love that man he portrays…I fell in love with a lie.  In the beginning… the good was so wonderful that it FAR outweighed the few little bad things and I thought it would get better…
    I have learned a lot through counseling…  Someone like my ex-husband cannot keep his facade up forever…. He has little to no respect for others..and will tell you anything you want to hear as long a there is a hook in it for him… He does not allow people to talk to one another for fear of his lies being found out… and it’s always someone else’s fault…not his…
    Trust me everyone…I have kicked myself for having let this many years of my life go to this man.
    I recently started on line dating and am finding a few players….but catch them in their games fairly early…
    They seem to be attractive, charismatic, fun, charming, and constantly telling you what you want to hear.. and just when you think.. “he could be a keeper” poof… it’s some sort of game of conquering etc..
    It’s disappointing and I want to find the real package!  So I’m watching and listening closely!! I sometimes wonder if I’m being tough on men, but then I see the game and realize… NOPE!

  25. 25

    Wow!  I just had to comment.  i’ve learned alot today from reading your comments.  Unfortunately, I learned the hard way that a “player” is someone who cannot and will not commit.  They are usually very selfish and self serving (all about me).  I dated a player for a while (FAR TOO LONG).  The sad part was that he loved me and I know he did, but he couldn’t stay away from other women.  He held on to me for dear life, sending roses, calling several times daily, weekends away together, dinner, gifts, the works, but he just couldn’t stay away from the other women.  They chased him, I didn’t.  Thankfully, he was honest about not being able to commit or leave the others alone.  I realized that his behavior wasn’t going to change anytime soon, so I got out as fast as I could.  Very painful situation to be in, hard to let go and move on, but even harder to stay.  I don’t wish that pain on anyone.  I say runaway as fast as you can.

    1. 25.1

      I’m 53 and I have never even thought guys were like this I fell in love with a married player.   And it hurts more then I can say . I love him.  I have been trying to let go . It is very hard

  26. 26

    JZ 25 – thanks for that comment.  I recently met a player.  It has really been the first time I’ve met that kind of person, and identifying the behaviour took me a bit of time.  But once I understood – I was outta there!

  27. 27

    I thankfully just dodged a player. He is very handsome and charismatic and is chased by lots of girls at my college. I know he likes me, and we had a flirtation going on for months, but I recently found out he has a girlfriend and is dating two other students at my school. We almost hooked up one day, but my instinct told me not to go there and I’m so glad it didn’t happen. I was happy and sad at the same time because I did like him, but grateful to find out who he really was before anything happened. Be careful out there!

  28. 28

    Let me add a few things to type 3 player:

    -tests every day (but he’s on whatsapp all day – he’s texting every one else as well)

    – he says he’s looking for love

    – he’s busier than US president

    – he takes you on excellent dates, knows your taste and never mixes you up

    – 3 to 4 months later you find out that weekend awaits with his friends is actually a weekend getaway with another girl who lives in a diff city..

    – you find out (thx to fb) and then you’re crushed. Can’t believe HE would be the guy who lied all along and you’re so upset and heartbroken and don’t want to talk to him ever again. Your body physically hurts from what it feels like withdrawal from him for about a month. And he moves on as quickly as snapping his fingers…

    1. 28.1

      Daniella, my ex is exactly the same as the characteristics you mentioned above. He broke up with me about 2 weeks ago and I already knew that coming. I checked his fb and found out he is a major player!

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