My boyfriend cheated in the past; should I break up with him? (Relationship and Dating Advice)

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.





10 Comments on My boyfriend cheated in the past; should I break up with him? (Relationship and Dating Advice)

  1. The second chance is because he lied to me about all this in the first place. I found this out when he told me his ex, who has a two year old child, wants a paternity test to see if it’s his. Then he said he would be honest with me but I found out he lied again, he said he did so because he thought I’d leave him if I found out about his past. I’ve cheated in the past so I understand that it’s possible to change but I’m not sure if I can get over it as long as he’s so friendly with so many exes. It’s something that I heard from a guy friend that bothers me the most: he wouldn’t have all of a sudden started talking to his ex who is promiscuous (the one with a 2 year old) if he was truly ready for a relationship. I could move on from this if he would give me a sure sign he changed but I don’t even know what that is

  2. @Emily……Talking to his ex suddenly, and flirting with other women certainly isn’t going to make you feel better. What’s the sign he’s changed? His actions not his words. He can tell you until he’s blue in the face that he’s changed, but if he keeps exhibiting these same behaviors it’s unlikely he has. The rest is what your gut is telling you.

  3. Hi guys, i also need help in this similar topic.

    First off sorry if it’s long. But i really need some advice from u guys.

    I broke up with my ex bf exactly 2 months ago. I was with him for 15 months. He’s 26 and i’m 20. He forgot to log his fb out, then i saw him messaging this girl a month before i found out. I saw this girl’s profile and she’s clearly a **** with **** flying everywhere and intentionally shown them off in every single profile picture of hers (i mean EVERY pics). I waited for a day to think things through and the next day i confronted him and told him i wanted to break up.

    Before this he had cheated on me with my own friend 2 months into relationship. I had forgiven him even though that time he didnt seemed to really sorry and i stupidly accept him back. Things were completely done with my friend and him but After that incident, i became very suspicious and he has shown some suspicious behaviour and i also can feel in my guts that he’s cheating again behind my back. Like random texts frm girls shows up in the middle of the night (he said it’s his clients, etc, excuses i feel). But i brushed it off since i didnt have any proof and he spends every single day with me so i thought maybe it was just some girls that had crush on him.

    But this time round i really cant take it anymore, i feel betrayed and hurt. So after a day of thinking, the next day i told him its done. I didnt scream didnt throw things, just talked calmly. He didnt deny it and his answer was “she didnt even reply”. Its true that girl didnt reply, maybe because she saw his profile picture were with me and want nothing to do with a man that has a gf. But still i told him it is unacceptable that he already think of cheating behind my back. I told him what if the girl had replied, it would be a diff situation now and he might have kissed her and slept with her.

    After that he said “fine” and leave from my place. He tried calling and i answered the first time, he said he didnt want to end the relationship but with a straight tone, he was not begging and didnt seem sad about it. I said theres no point anymore since he broke my trust again and i am tired of this and hang up. He called again few times but i didnt pick up, i was so sad at that time. But later at night he didnt even call, didnt even show up at my place, did nothing. I waited for 6 days for him to apologize and fight for us or at least if he didnt want us anymore he can end things nicely. But nothing came from him.

    The night of day six After i told him i want to break up, i saw his fb and i was shocked. All my pictures and our pics together are gone. I obviously was very devastated and ended up texting him few times and the last text i told him i still love him and want him to try. But there are no replies from him. finally 2 weeks after BU i text him to call me for the last time since we didnt even get to end things properly. He called me basically just said he’s tired, its over, told me to pick myself up and move on. I didnt beg or cry at the phone conversation. Just quietly listened to him.

    2 months have passed now. No contact frm him at all til today. Sometimes im just confused because before i found out abt this and told him to break up. Things were good, in fact better than before, he didnt show signs of cheating, always spends time with me, always happy, and the last night that we met, he even spend the night together with me. He is very close to my parents and they treat him very nicely even though he is from another country. They treat him like he’s their own son. My mother are very devastated and disappointed that he would change to he is now.

    Now all i feel is sadness and emptiness. Never thought that he will give up so easily after everything. I know what he did is wrong, but i do love him and just wish he can show he is sorry and fight for us. I apologize again if it’s long. I’ve really been wanting to post my story here and listen to some advice. Thank you for reading this and for your help. Any comments will be appreciated

  4. @Hannah……..We’re sorry you’re feeling so sad, but you’re forgetting why you broke up with him in the first place. You’re letting your loneliness and sadness cloud your mind. It’s not like he did one questionable thing and you worked through that together. He cheated on you twice. That shows a pattern of behavior, which is difficult to break. He’s also shown no signs of remorse, nor signs that he’s willing to work on changing his ways. Breaking up always feels sad. It’s like losing a part of yourself. But that sadness doesn’t mean that you’re meant to be with this guy. Our suggestion: Lean on your family and friends, try to be strong, and move on. It sounds like he is. And if so, he’s doing you a favor. Hang in there and take care. Any more questions? Ask away. ps. We hope you’ll share our site with all of your friends. Follow us on Twitter; @TGPBuzz. And take a moment to help a fellow reader. Please VOTE on the Ask our Audience page. Thanks!

  5. Hey guys,
    I wrote a lot but I did that so you guys could really under my situation. I have been so confused about my relationship lately. More than 2 years ago I got with my now ex-boyfriend which I sort of consider boyfriend because we are still trying to figure things out. Anyways, I got with him and I knew he had a past with flirting with a lot of girls because he was a friend before so I knew that he really didn’t have many girlfriends but a big flirt. We got together and it was something different for me because I was much more attractive than him and he was considered one of the “luckiest” guys when we got together. When I got with him a lot of his friends started hating on me and his ex girlfriend appeared more than ever always saying that he still texts her but she was really obsessed with him and besides I was much better looking than her so I felt like he wouldn’t go back to her because he was only with her for 4 months and cheated on her all the time and I know because he would tell everyone. Anyways, she was always trying to be around the family and him, she would post his name all over her statuses, post depressing things I really knew that this girl was jealous because all she did was try to tell everyone how he still wants her even though he was taken by me. Although I never seen any of her on his cellphone, text, Facebook and so forth he had a slip up with another girl not this ex. I got his Facebook open on his phone and I saw him messaging another random girl from school calling each other “babe” and talking about how they should hang out. So we broke up because I consider that cheating and he went through a deep depression mode that even his friends never seen before. He would write me letters and cry to me and his friends, talking about how he loves me so much and I started to believe him because he really showed me that he was sincere. We got back together and every thing was great, we were together almost every day we went to college together and we were so perfect. Although we were good, I went through his phone and I saw that he was texting girls that he would always flirt with before. It was never inappropriate it was just conversations but it got me mad because he was speaking to girls I told him not to speak to. I would always speak to a lot of guys as well but I really had no interest so we would constantly fight about that and break up and then get back together. The problem with him is he just kept texting the girls but not repeatedly. I would go for 4 months not seeing anything but then the texting would appear again and it would hurt me so much so we just ended up braking up about 10 months ago. Although we never stopped talking ever since we broke up because we couldn’t let go of each other. Recently, a friend came to me and she told me she is going to confess to me about him. She told me that the whole 2 years he was with me he had sex with more than 7 girls, that he never stopped sleeping with his ex-girlfriend. Also, she told me he always remembered numbers and thats why I never seen any girls text in his phone because he was good at hiding everything. This just makes me go crazy because I don’t know who to believe. I never caught him kissing another girl, sending inappropriate text or let alone sleeping with another girl so it makes me suspicious in who to believe. He proved to me he loved me, his family loves me, and he did absolutely everything for me but my friend who comes telling me this stuff just makes me hate him and not want to work things out like we were planning to. Also, she is his friend and she said everything she knows is from what my ex-boyfriend told her but she’s known to know rumors about everyone. She even said things about me that were completely untrue so it makes me suspicious of everything she told me. I don’t know who to believe because what I had with my ex-boyfriend was something special and all these “rumors” I heard all the time ever since we got togehter really confuse everything because I have never seen any of what they say for about 3 years. I believe cheaters eventually get caught if they are sleeping with so many girls but I have never seen it so it is hard to believe it. So after I heard all of those things everything he tells me, everything he showed me and continues to tells me I see it as a lie.

    Who should I believe? And what should I do with the relationship, work for it or let it go?

  6. @Stephanie…….We suggest you look at the evidence. Past. Present. And then decide for yourself. Clearly he has a tendency to flirt. He’s cheated on girlfriends in the past. He also cheated on you. (Isn’t that why you initially broke up with him?) Also, your relationship has been on and off for the last 2 years. Maybe the “on” periods are great, but there’s certainly a reason there are “off” periods as well. When things are solid between two people, there aren’t usually “off” periods. But before you condemn him to “once a cheater, always a cheater” ask yourself some questions and do some detective work. 1. When you were dating, did he have the time to actually cheat? Did you see him every day? Or did he have some time to himself? Unaccounted time could support your friend’s accusations. 2. Is your girlfriend generally a reliable source? Does she have an interest in him? Has she always been a pretty supportive friend? Does she have a reason to lie? How did she act when she came to tell you this? Was she sad for you? 3. Why would your boyfriend tell her all of this stuff?
    Here’s how we see your relationship: There’s a lot of passion here, but only some of it’s good. Your constant breaking up and getting back together does not bode well for a long-term relationship. It shows that something isn’t working between the two of you. He has a pattern of behavior—cheating/flirting—that’s going to be hard to change, and make you not trust him completely.
    Stephanie, you need to think long and hard about what you want here. Maybe you have strong feelings for him, but make sure the relationship is actually going to make you happy. Your thoughts? Questions? Ask away. ps. We do hope you’ll share our site with all of your friends. Follow us on Twitter: @TGPBuzz. Share on Facebook or other social networking sites. And take a moment to help a fellow reader. Please VOTE on our Ask our Audience page. Thanks!

  7. Dear Guys & Emily,

    I have similar situation. I have been seeing a guy in his mid 50’s for 2 years (I am 48). In the beginning he was asking me to be exclusive, wants us to build something, etc. A month into it I find out that he is seeing his ex-wife (divorced 14 years) and had been seeing her for two years (she found my number in his phone and called me). He told me it was all a mistake, she read more into it than what it was, etc. I gave him the benefit of the doubt, but something kept bothering me about him, I just had an inner sense that he was not honest about things. We continued on for several months, and one day I told him how I felt about him, and he said “Well, its all about sex for me.” So, I broke it off and for two months he was gone, then he leaves a note on my car saying he misses me, he is sorry, please give him another chance. I did, but things just didn’t feel right inside. I finally point blank asked him if he was seeing other people and he (defensively) said “No. Why do ask me that?” I let it go (foolishly) and tried to believe him, but things he said just did not add up. Finally, I did a low-down thing and went into his e-mail and found out he was seeing not only his ex-wife, but had some deep relationship with another woman and also had slept with some woman he barely knew. I was so hurt, confronted him, and he was mad that I went into his e-mail. I broke it off, but he kept coming back to me wanting to get together, etc. I did, but never trusted him again. Recently, after being together 2 times a week or so, he just disappears for an entire month. I didn’t call him, I just tried to move on and then again, he calls me and gives me another line about “us”. We spend two nice days together, and he disappears again, no word for three days. I finally called him because I was tired of this, and I told him if he was going to keep coming in and out of my life, to just leave me alone so I can move on. He said “O.K., I will, I will.” I just started crying and hung up. Why do guys do this? Why keep lying over and over !
    for 2-ye
    ars? Just to get sex? He was obviously getting it elsewhere, why keep hurting me? I didn’t think men in their 50’s would still play this game. I am 48 years old and I feel crushed like I did when my first boyfriend hurt me at 16! He kept it going, not me. I backed off. He just kept coming around like a bad penny (but yes, I let him back in). So my question is, is he just a cad? A 55 year old player? Or, do you think it is my fault for letting it happen and being so naive and forgiving? I know I have been stupid, but I loved him. Please give me some advice. Thank you.

  8. @Buffy…..We’re sorry. You seem to have a pretty accurate view on of all this. This guy is bad news, at least for you. He’s likely playing his ex and this other woman as well. It might be all about sex for him, or it could just be about the conquest. This isn’t your fault, but you’re not doing yourself any favors by allowing him back in your life. You deserve better than that, but you have to believe that before you can make it happen. Do you? Our advice: Learn from this and move on. And when your gut keeps telling you that something isn’t right, trust it. There are good guys out there. So don’t give up. take care.

  9. My boyfriend cheated on me in the past, I’ve decided to forgive him and keep the relationship going since he seemed to be remorseful and honest about not doing it again. He’s about to get a job that will require him to travel 2 weeks at a time which is making me uncomfortable to think he might cheat or try something that I wouldn’t want him to do while he’s away, how can I tell him this? should I just end it since I feel like I would not be able to trust him while he’d be away? should we take a break while he has the job?

  10. @mp……Just because you love him doesn’t mean he’s right for you. You don’t want to be with a guy you can’t trust. You need to give this some serious thought. We can’t tell you what’s right.

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