Dating A Man Who Used To Get Around? These Awkward Things May Happen

July 1, 2015  |  
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People can change. Plenty of men go through a phase where they sleep with anything that has two legs only to go on and become perfectly good, loyal boyfriends. But whomever they are, boyfriends will have to deal with some leftovers from their promiscuous days. If you’re dating a man who used to get around, these awkward things will happen. We’re not telling you as a cautionary tale or urging you not to date a former playboy, we’re just saying be prepared so hopefully you don’t freak out when the time comes.

His neighbors will look confused

His neighbors are used to seeing different women come out of his apartment every day. Now it’s the same woman every day: You. Expect these nosy neighbors to give you the crazy eye in the beginning. You’ll think they don’t like you but really they’re just in a state of shock and curious about the woman who managed to center your boo’s formerly wandering eye.

Condoms everywhere

You’ll find them in his pockets when you fold laundry for him, in the glove compartment of his car, in his laptop case. They will be all over the place. Hey, at least he practiced safe sex.

People will assume you’re a fling

People who know his old ways will talk to you as if you’re just around for the night. You’ll have to explain over and over again that you’re his girlfriend.

You’ll see his “exes” everywhere

If he really got around, you’ll notice different women giving you dirty looks. Yeah, he probably slept with them.

Or at least friends of his “exes”

If you don’t encounter the women he slept with, you may run into their buddies. Promiscuous men cast wide nets, and somebody knows them everywhere they go. Those friends will give you a pitying look as if to say, “Honey, you don’t know what you’re getting yourself into.”

He’s banned from some places

Men who used to get around tend to fool around in places they’re not supposed to.

He’ll cut off his own stories

He’ll lose himself for a minute and start joyfully reminiscing about that time he was at that tiki bar, and there were all those waitresses with coconut bras and…(gulp)…never mind.

He’s still a flirt

He may be totally loyal to you, but if he used to be out in the world sowing his wild oats, it will take time for him to stop flirting with everyone.

Some women still hit him up, thinking he’s single

His phone will go off a lot, and you will see women’s names on there that you’ve never heard of. They are old flames back in town trying to see “What’s up?” Or they are women he used to hook up with who are suddenly single and ready to mingle. They didn’t get word that he is taken now.

Some women will think they can get him to step out on you

Some of them did get the word that he’s taken but don’t believe his new loyal ways will last for long. So they reach out and try to test him.

Suspicious Facebook photos

There will be a lot of pictures of him on social media with different friend groups (including many different women). You’ll eye them, trying to guess who in the images he actually slept with.

Courtesy feminine products in his home

You’ll encounter a box of tampons or pink razors in his house—items he bought when he used to have visitors over a lot.

He’ll be too good in bed

You will have a hard time enjoying all of his tricks because you may be too busy wondering where and who he picked them up from.

You won’t like his friends

You may resent them for encouraging his past shenanigans. All these awkward encounters are partly their fault!

His friends may not like you

You’ve stolen their wildest friend. They used to count on him for glory stories of hookups, and now, you’ve taken him away.

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