Hi Guys,

My boyfriend has cheated on several of his exes in the past. He says they were cheating too, which to me is irrelevant. He still texts some of his exes and other girls he slept with. He’s never propositioned any—as far as I know— although he sometimes shares inappropriate stuff with them. He’s also slept around with a lot of women in the past. I’m not sure if I should break up with him, give him another chance, or if I’m being unreasonable to begin with. He assures me he’s changed but I’m not sure about that. He’s 20 and has a full time job and I’m 21 and going to college.

Some advice please?


Dear Emily,

Thanks for your question.

What happened to his first chance? Did we miss something? Why is he now on his second chance? Has he done something besides the occasional inappropriate conversation? (Yes, we agree that needs to stop.) We gathered that he hasn’t actually cheated on you. So this is just a feeling you have, right? A worry that he hasn’t really changed, and that these behaviors he’s exhibited in the past are lying dormant, waiting to resurface at their earliest convenience?

So this all comes down to you Emily. Are you truly able to give this guy a clean slate? And do you think you’ll ever completely trust him? Because you know as well as us, that if you’re constantly wondering and worrying about what he’s doing, or might do in the future, you’re not going to enjoy the relationship. With that mindset, it won’t matter whether he’s cheating or not. You’ll still feel exactly the same way.

It is true that changing a behavior like cheating is not easy to do. The person has to want to change, and then be willing to do the work required to change. And we’d say most 20 year-olds aren’t quite there yet. But once again, we ask you what do you think? What’s your gut telling you? You certainly know the guy better than we do. And if you asked 100 people what you should do, everyone would give you a different answer. (Of course all these answers would be based on personal history, and how each person feels about cheating in general. Which means none of those answers would actually help you solve your problem.)

Our advice: If you truly think you can get past the thought of him cheating, then by all means give him a chance, or a second chance. (Of course keep your eyes open moving forward.) But if the worry constantly gnaws at you, and you can’t let it go, it’s probably time to move on. You might not be the kind of person that can handle the uncertainty of not knowing for sure. And that’s an important thing for you to note about yourself. (You’re certainly not alone in that regard. So no worries.) But that information will help you make better choices in the future.

What do you think? Any follow-up questions? Ask away. And definitely keep us posted on what you decide to do. (In the comments’ section)

Take care and good luck,


ps. We hope you’ll share our site with all of your friends. Follow us on Twitter: @TGPBuzz. Also, help a fellow reader out. VOTE on the Ask our Audience page. Thanks.