Realities Of Dating Someone Who Used To Be A Player

July 13, 2018  |  
1 of 15 couple laughing in bar, close-up

When men are younger, they think that the goal is to just sleep with as many women as possible. Of course, most of them don’t get to achieve that goal. In most cases, in fact, men will tell you their number is lower than they wish it were (the number of people they’ve slept with) and women will tell you it’s higher than they wish it were. Why’s that? Well, because, women don’t usually need to look too far to find someone who will sleep with them. Ask, and we receive. And sometimes we regret asking. That’s not the same for most men. That being said, there are those few guys in your town—you know who they are—who are just so undeniably hot and charming that they did get around in their younger days. But even those guys eventually settle down, get into serious relationships, and even get married. If you wind up with one of those guys then you know about these realities of dating someone who used to get around a lot.


Women think they can creep

Other women hit on him right in front of you. They either assume that you aren’t anything serious, or they assume he’d just cheat on you if you were. Either way, a lot of women don’t really respect that you’re standing there, holding his hand.


Women don’t believe he’s changed

Your female friends have a very hard time believing that he’s changed. Most men like that do have to change eventually, but it can be hard for anyone who has witnessed their player days to believe that change has occurred.


You run into someone everywhere

Everywhere you go, you run into a problematic person. Even if it isn’t someone with whom he slept, it’s the friend of someone he slept with, or the new boyfriend of someone he slept with.


You have to be very confident

You have to be very confident to date someone who got around in the past. If you believe, in your gut, that he’s not about that life anymore, then that’s what you have to go on. You don’t get to have a totally normal, peaceful existence for a while…so your confidence will have to carry you through.


He’ll know your body too well

Sometimes you won’t be able to enjoy all of the ways he knows how to make you feel good in bed because you’ll be too busy wondering, “Where did he learn that? Nobody knows that!”


His friends are in awe of you

His friends are in awe of you. They never thought anyone would get this guy to settle down. They look at you like some sort of genius or god. They have deep respect for you.


You need a good sense of humor

You need a good sense of humor. A really good one. You never know when he’ll say that he can’t go to some bar you want to go to because he got banned from there for having sex in the bathroom.


He edits a lot of stories

You notice that he has to edit a lot of his stories. There are holes. He jumps over big time periods. That’s because the true story would involve a lot of hookups with a lot of other people.


He understands women too well

Sometimes the little details he knows—like the types of foods women like to order or destinations they like or habits they have—freak you out. You know he picked those up during his player days.


Strangers treat you like a fling (at first)

Acquaintances of his meet you and treat you like a fling. He introduces you as his girlfriend but, they don’t really take an interest in you or ask you questions the way they would if they truly believed you were a serious girlfriend.


To some friends, you’re the enemy

Some of his friends are still getting around, and they’re angry with you for taking away their wingman. They may even try to make you feel insecure about your relationship with subtle digs.


There’s always just a degree of separation

Everyone in his life has just a degree or two of separation from someone he once slept with. I mean, let’s put it this way: if a friend’s cousin, sister, female friend, or female colleague came to town…he may have gotten in there.


People warn you about him

People—strangers you don’t even know—come up to you and warn you about him. You’ll be at dinner, your boyfriend will get up to use the restroom, and some woman will walk over to you and suggest you stay far away from that man.


You find female items in his home

You may find a leftover female item or two, like a box of tampons, a bikini bottom, or a compact. You just have to roll with it. Or keep them.


He knows the streets too well

Whatever neighborhood you’re in, he knows where to park/where to eat/where the dog park is. It’s probably because he was, at one time, hooking up with someone who lived there.

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