He cheated; and he had sex while we were broken up

Dear Guys,

I’ll try to make this short and sweet.

I’m in a 4-5 year long distant relationship with a guy who’s cheated on me 3 times—flirting, texting, sexting. He was also on dating web sites. Etc w/ other females. Every time I caught him, we would break up for a few months but somehow always get back together. The 4th time I caught him, I decided it was over! I couldn’t take it. We broke up for 6 months (May-Nov.) We started texting again a little in November-January but later found out he was also talking to someone else during that same time. I gave up and cut off all connections with him from that January-August of this year. In that time he never once tried to contact me until recently (2weeks ago) he sent flowers and multiple hand written notes about how sorry he was and how much he loves me and wants me back. He also claimed to be a changed man.

Seven days ago we started talking again via phone/text and I just had a burning question: Had he been sexual with another female?His reply was, yes. He told me it was only one time in October of last year. I feel hurt. If he really loved me, then why did he feel the need to be intimate with someone else knowing he want me back? I had plenty of opportunities to sleep around too, but I always denied the offers. Today he insists “that was the past” and that he wants a future with me. I want to be able to forgive and forget seeing we weren’t together. Now all day everyday I think of it and it just eats my heart out. The thought of him having sex with someone pisses me off and in return I get really angry at him. I hate that I dwell on it.

Am I over thinking this? How do I really move on? I really do love him. I just don’t know how much more heart ache I can take. I want to trust him more as well but I don’t know how :-/ HELP!


Dear Anastasia,

Thanks for your question. Pardon our skepticism, but the red-flags are flying high.

Him having sex with someone while you were broken up is the least of your worries. In fact, yes, you are overreacting. You weren’t together when he had sex with this other woman. (Although you can be sure that he had sex more than one time.) But even still, what he did while the two of you were broken up is not your concern. Maybe you’re upset because you passed up opportunities and he didn’t, but still, it’s unfair of you to expect him to behave the way you did. And yes, a guy can have sex with one woman even if he loves another. Guys are all about compartmentalizing.

However, what he did while the two of you were together is a whole other matter. We’re not sure why he’s had a sudden change of heart, but based on his previous behavior it’s probably because he’s lonely and/or horny. He may say he’s changed—and it’s possible—but changing this kind of behavior usually takes some serious work. Has he been seeing a therapist or some other professional? Has he processed his feelings with anyone besides himself? Has he been exploring why he feels the need to cheat when he’s in a relationship? (Believe us, you’re not the only one he’s cheated on.) What makes you think he’s really changed besides him saying it?

So the question Anastasia is, why do you want him back? Sure, he might have some great qualities, but if you can’t trust him, there’s not much of a relationship. Don’t settle. The person you ultimately end up with should be as committed to the relationship as you. Do you think this guy fits the bill? And do you really think you’ll be able to trust him again?

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Take care,


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2 Comments on He cheated; and he had sex while we were broken up

  1. Maria Rossi // February 26, 2013 at 8:31 pm //

    broke up with me this past November due to personal issues that he was dealing with such as the passing of his sister last year. We decided to remain best friends after that and we both suggested a future relationship. Unfortunately, I found out on February 5th that he slept with a girl in the month of January. Also, after we broke up, they became close. Before I knew all this was happening, he would tell me that he ‘loves me’ and cares about me. Furthermore, how he couldn’t imagine his life without me. When he told me about the girl and everything, he was crying and saying how he fucked up things with me,etc. I defriended him off Facebook, but his mom and I are still friends. I posted quotes on my Facebook wall and she would comment saying that “he misses his diamond” or just trying to indirectly state that he misses me;hence, this was twice. I even messages her to tell her what happened because I knew it wouldn’t do it time or tell her everything. Anyway, she said in a message to me….”Maybe one day you two will be together and that will even be if you would want too after he realizes how much he misses you.” Anyway, it’s been two weeks since we last spoke to each other. I miss him so much. I knew he truly didn’t want anything to happen between us, but I guess he didn’t think it would catch up to him. Anyway, do you’ll think he’ll try to contact me? Do you think he really regrets what he did? I’m just so hurt and confused

  2. @Maria…..He may regret what he did but that doesn’t change things. We have no idea if he’ll contact you, but you shouldn’t contact him. Maybe it’s time to move on? We’re sorry.

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