How To Cope When His Past Makes You Uncomfortable

When you finally meet someone you really like, you want to learn as much about him as you can. Sometimes this leads you into strange new territory and you learn things you wish you hadn’t. We all have histories, and some of ours are darker than others, but does that mean you should break up with someone just because you don’t think you can handle his past? After all, just because he was one way in the past doesn’t mean he hasn’t changed since then.

  1. He’s cheated before. People cheat — we’re human and we make mistakes. There’s a chance that if he’s cheated before, he might do it again, but you still want to give him the benefit of a doubt. If he truly believes you’re The One,  there’s also a good chance he won’t do that to you. This one is totally your call.
  2. He’s been with a MILLION women. Or like, more than 50, because that’s pretty close to a million, right? It’s totally fine if you’re uncomfortable with the number of women he’s slept with, especially if he can’t even give you a number or remember most of their names, because that’s pretty disgusting. The only thing to really do here might be to just accept it and come to terms with that fact, because there’s absolutely nothing else you can do about it. The deeds have been done. Just make sure he cuts that crap out now that he’s with you.
  3. His exes are amazing, beautiful, and everything you’re not. So now you’ve uncovered the harsh truth that he’s apparently only dated supermodels before, or Nobel Prize winners, or professional cheerleaders — and you’re afraid you can’t compare. You’re afraid you have zero chances of holding on to him. But he’s not with them now, is he? No, because he’s with you. That has to mean something. Don’t feel threatened by the people he’s been with, because they’re not together anymore for a reason.
  4. He used to have a drug/alcohol problem. Addiction is a serious thing, and if he used to have a problem but got himself together, it shows that he cares and wants to help himself. You can’t force someone to kick a habit because they can always go back to it, so if he’s trying now, it means something. No one is perfect and we’ve all made mistakes, so definitely try to give him a chance and see past that part of his life if he’s well on his way to recovery.
  5. He used to be involved with the wrong crowd. When we’re young, we’re highly impressionable. That means that it’s not really that hard to fall in with the wrong kind of people. He would just have had to have been in the wrong place at the wrong time. The real issue is whether or not he’s still in touch with this crowd or whether he’s still being influenced by them. If there’s still a chance he can go back to that life, that definitely is a reason for concern, but the best thing to do here would be to talk about it and see if he still has contact.
  6. He’s been emotionally scarred.  Dealing with someone who’s been emotionally scarred is tough because he may also suspect you of doing him wrong too, even if he has no real reason to distrust you. For someone who’s been hurt before, sometimes it’s really hard to trust anyone completely, and not ever feeling certain that he feels the same way about you as you do about him might be a hard reality to face. You just need to try your best to reassure him you would never betray or hurt him, and hopefully over time he’ll see you’re truly different.
  7. He’s done things he really regrets. It’s possible that his past is full of things he wishes he’d never done. If those regrets are too heavy for him to ever recover from, it can be a problem. If you really care about him, try helping him through it and convincing him that these things happened long ago. He wasn’t the same person back then, and it’s unhealthy to live a life full of regrets. Try to get him to look to the future, as opposed to the past — and just know that if he regrets something, it does show that he cares and he’s not a bad person, even if the thing he did makes it seem that way.
Chelsey is a freelance writer in NYC. She's pretty normal by today's standards, or at least that's what her mother tells her.