Q.

Hi Meredith,

I’m over 40 and married with kids. I have a close friend that I have had in my life for over two decades who is also married with kids.

He had a girlfriend when we met, and while I instantly was attracted to him, I pushed it aside since he wasn’t single. I found out years later that he also had feelings for me during that entire period. He finally admitted them to me many years into our friendship, when I had a boyfriend.

What he didn’t know was that I had broken up with that boyfriend the day before. We jumped into an undefined relationship I was not ready for, and we weren’t good at communicating with each other.

A few months into this “dating,” we got into a heated argument over the phone. We were both stubborn and neither of us admitted fault or reached out to the other person. Then, a few months later, I got a sudden opportunity for a job and moved out of the area. I broke the silence by telling him I was moving.

I heard from mutual friends that he said he lost the love of his life, the person he thought he’d marry. 

It took a bit for us to really speak to each other again after this argument and my move, but after a few years, we started to mend our friendship – though it was mired with a hookup almost instantly into our beginning to talk again. 

One time when visiting, one of his close friends asked me when I was moving back, because he said my ex was not over me and wanted to marry me. I told this friend that I needed to have that discussion directly, and he really needed to be the one to say it. That was met with “you know how he feels about you.” It was all on me?

But, he (the ex) never said anything, and when he did, it was in a way that I interpreted as jokey, or he only said it when he was drunk.

We visited each other a lot at that point and we were firmly in a situationship. We both tried to find work near each other, but one time when I said I was just going to move back, he told me that was great but not to do it for him because he didn’t want the pressure of the relationship.

We teetered back and forth in this weird relationship that we both never really fully committed to. In hindsight, I wish I was more honest about how I was feeling and what I wanted. I also felt like I wasn’t in the driver’s seat and needed to wait for him to decide.

One day I was faced with another life decision related to work that would keep me in the area I was living in. I decided I needed to be really honest about how I was feeling and wrote him an email detailing that I wanted to be with him. I also shared how the situationship and some of what he told me was confusing and hard for me. I ended it with letting him know that I wouldn’t ask him about this if he didn’t bring it up.

He never responded or brought it up, though we continued talking and hooking up.

I tried to move on so many times and then started dating a lot of different men to try and get over him. I met my husband who is truly a wonderful partner and the father of my children. 

During a time when the ex was still single, but I was with my now-husband, he told me he was sad I moved on. We texted (I know, not the best format for this) about our feelings. I told him I wish we had talked about all of this, and he told me he had read my email and decided right after reading it that he thought we’d have a great life together but fight a lot, and he decided that rather than risk a fight that might make us part ways completely, he chose to keep me in his life by my staying his friend.

It was very confusing and made me sad. 

He then met his wife, who is a version of a girl he used to date, whom he called “safe” because she was sweet and would tell him what to do. Basically, a mom.

I’m rambling a lot but what I’m getting at is that I still think about him far too often and am having a hard time because I keep thinking about the “what ifs.”

I’ve talked to my therapist about this once before, and he told me to cut contact completely. But it’s a relationship I do not want to lose him in my life. 

I know sometimes there are multiple matches for people but the timing doesn’t work. I think that was it for us. I feel awful because I don’t want to hurt my husband or children. I think if it were meant to be, we would be together, but why am I struggling? It’s not constant, but sometimes I really have a hard time. 

Do you have any suggestions that don’t go as far as cutting him out? I also have a hard time thinking that he no longer has those feelings for me (he shouldn’t, he’s married) and I don’t know why. Help?

– What if?