My Boyfriend Has Cheated on Me a Bunch of Times. Should I Marry Him?

I am a 46-year-old, twice divorced, mother of 3, dating a man with whom I had a serious relationship in my 20’s.

Back then, I ended the relationship because I never trusted him (he was somewhat of a player, 8 years older, while I was a naive law student who had had one previous relationship) and although we were very compatible and I loved him very much, I did not see a future with him.

After my 2nd divorce, I reached out to him; we chatted for hours and made a date to meet up for dinner and drinks. That date lasted 7 hours, we both felt an immediate re-connection, and I had this amazing feeling that we had both grown up and were ready to be in a more mature relationship.

The first several months were great; we had many fun dates and became intimate within the first month. There were some red flags early on, like when I asked if he was seeing anyone else and he laughed it off — I thought he was saying my question was ridiculous — after all, he had already told me he loved me.

Turns out, I was wrong. Five months into the relationship, I learned that he had been dating someone very seriously immediately before we started dating, that he was not over her when we started dating, and in fact had tried to get back together with her nearly 3 months after we started dating (she said no).

Also, he had a female “friend” (the former best friend of the aforementioned serious girlfriend) who he spent an inordinate amount of time with (and actually lied to me about sleeping at her house) but insisted there was nothing going on with her.

It made me uneasy but he continued to spend time with her. He routinely didn’t answer his phone, claimed he didn’t hear it, or the phone was dead, or made some other excuse, and was extremely protective of his phone. All along, he insisted there was nothing going on and that I was insecure and pathetic for thinking otherwise. This went on for months.

Finally, 9 months into this relationship, things came to a head when I caught him in a lie. We had a big fight and nearly broke up but somehow ended up staying together. Things changed dramatically after that fight. He started to always answer the phone when I called. He no longer went out with friends without me. He called when he said he would, stopped drinking and partying, stopped spending time with the female friend, and really stepped up as a boyfriend.

I did not ask for any of this — he just did it.

Six months later, I did something I now regret. I looked at his phone records, and found out a few things: In the beginning, when I thought we were exclusive, he was still dating other people, and even took one of them out for Valentine’s Day. But that isn’t the worst part. He actually had another girlfriend — someone whose name I had never heard before — for at least 4 months prior to the “big fight”.

I found hundreds of phone calls and text messages between them, including a 275 minute call on the night of my son’s birthday, pictures of them together, and even spoke to her on the phone where she confirmed the relationship. He ended that relationship just prior to the “big fight”. He denied everything and has still never really apologized. I tried to break up with him but I just didn’t want to let him go. That was almost 2 years ago.

Now, he is doing everything right now, but I am having so much trouble forgetting what happened. I am tortured by it. I try my best to trust him but it is very difficult. He tells me that my “trust issues” are my issues and refuses to acknowledge his part in it.

We generally get along and only fight when my insecurities get the best of me. I love him and genuinely do not believe he is cheating on me now, but I am not sure whether to believe it will never happen in the future. He keeps hinting at getting married but I am hesitant since I was already divorced twice, there are kids involved, and I really don’t want to make another mistake.

My question is — do people really change? Did that big fight — where he almost lost me — make him realize how important I am to him so that he won’t put the relationship at risk again? Can I marry him even though I still feel some much pain from the things he did behind my back? Will I ever get over the pain his cheating caused? I have now given more than 3 years of my life to this guy (6 years total) and am really struggling to figure out if I should marry him or break up with him. Please help.

Jen

There are “rules” and there are “exceptions to rules. My job is to give the rules, even though I’m well aware that there are MILLIONS of exceptions to them.

There are “rules” and there are “exceptions to rules. My job is to give the rules, even though I’m well aware that there are MILLIONS of exceptions to them.

Ex. Man pays for first date. I know a guy who got married although he didn’t pay for their first date, however, that doesn’t mean that going dutch is a good strategy for a first date.

So, Jen, I’m going to point out how many Love U “rules” you went against in this one painfully written email. Let it be noted that I am really sorry this happened to you and deeply sympathetic to your pain. However, I wouldn’t be doing my job if I didn’t point out to my readers how many things could have been played differently.

I’m dating a man with whom I had a serious relationship in my 20’s. Sure, someone goes back to their high school reunion and falls in love. Sure, someone reaches out to a recently divorced man on Facebook and tries to suss out if he’s available. Sure, someone rekindles things with an ex. But, in general, going back to the well is a bad idea for one obvious reason — you already tried dating and it didn’t work out! Instead of trying out all the other single available men in the world, you’re going to try AGAIN with a man who didn’t work out the first time around.

I never trusted him — Relationships are based on trust. If you didn’t trust him 20 years ago, why invest your time and faith in him now? Because you “loved him very much?” Not a good answer.

I had this amazing feeling that we had both grown up and were ready to be in a more mature relationship.   That’s a feeling, not a fact. It’s based on brain chemistry and wishful thinking, not based on any evidence that your boyfriend had developed a stronger character over time.

The first several months were great; we had many fun dates and became intimate within the first month. This describes the first several months of EVERY relationship. It doesn’t mean yours is special.

There were some red flags early on, like when I asked if he was seeing anyone else and he laughed it off. Believe the negatives, ignore the positives.

I learned that he had been dating someone very seriously immediately before we started dating, that he was not over her when we started dating, and in fact had tried to get back together with her nearly 3 months after we started dating (she said no).   And you stayed?

Also, he had a female “friend” (the former best friend of the aforementioned serious girlfriend) who he spent an inordinate amount of time with (and actually lied to me about sleeping at her house) but insisted there was nothing going on with her.   And you stayed?!

It made me uneasy but he continued to spend time with her. He routinely didn’t answer his phone, claimed he didn’t hear it, or the phone was dead, or made some other excuse, and was extremely protective of his phone. All along, he insisted there was nothing going on and that I was insecure and pathetic for thinking otherwise. This went on for months. And you stayed?!!

9 months into this relationship, things came to a head when I caught him in a lie.   And you stayed?!!!

He actually had another girlfriend — someone whose name I had never heard before — for at least 4 months prior to the “big fight”. I found hundreds of phone calls and text messages between them, including a 275 minute call on the night of my son’s birthday, pictures of them together, and even spoke to her on the phone where she confirmed the relationship. He ended that relationship just prior to the “big fight”. He denied everything and has still never really apologized. I tried to break up with him but I just didn’t want to let him go. That was almost 2 years ago. And you stayed?!!!!

Now, he is doing everything right now, but I am having so much trouble forgetting what happened. I am tortured by it. I try my best to trust him but it is very difficult. He tells me that my “trust issues” are my issues and refuses to acknowledge his part in it. This is called gaslighting. Run.

My question is — do people really change?

No!

Did that big fight — where he almost lost me — make him realize how important I am to him so that he won’t put the relationship at risk again?

No!

Can I marry him even though I still feel some much pain from the things he did behind my back?

No!!

What is painfully obvious to everybody except you, Jen, is that there is nothing confusing about your situation at all — apart from why you are still considering marrying a man you don’t trust who has lied to you and cheated on you repeatedly.

Please, get out and believe me when I tell you that virtually ANYBODY ON EARTH is a better husband candidate than your current “boyfriend.”

I know that’s not what you want to hear but there is honestly no other interpretation of your situation.

If you marry this guy and he cheats on you, don’t blame him. Blame yourself for willingly marrying a known cheater.

And I normally don’t do this, but your situation is exceptional: please click here to get yourself healthy and find yourself a better man soon.

You deserve much more than what you’re settling for right now.