Hi Meredith,

I’m embarking on a new relationship and I’m finding myself hung up on some things that happened in the past with this guy (I’ll call him Sam) who I have known for over 10 years.

A few years ago, I felt something brewing with Sam. We couldn’t deny the chemistry but both of us were too young and scared to do anything about it, resulting in lots of missed opportunity. I moved to a different city for a bit and we continued our overly friendly relationship, seeing each other every other weekend or whenever I was able to travel home. As luck would have it, I received an amazing job offer back home and took it. Along with the new job, I finally decided to come clean about my feelings since we were back in the same zip code and could actually give this a go. I was absolutely blindsided to find out he had a girlfriend, a brand new girl at his work. Despite him saying he felt the same way — that our missed opportunities were his biggest regret in his life, and that if he had only known how I felt a few months earlier things would be different — he still chose this new girl over me and I was heartbroken and in shock/disbelief.

I moved on with my life and a few months later found myself in a serious relationship. I was happy. The relationship ran its course and ended last summer. A few months later, Sam and his girlfriend broke up. We continued our friendship, but I was still “over it” (or so I thought) and only categorized our time together as friends.

Almost a year after our respective breakups, Sam blindsided me again by telling me that he still had feelings for me and thought we owed it to each other to see what happens. I was initially hesitant and told him I thought we were past this. He used the “bad timing” excuse as to why it never worked out. Needless to say, I gave him another chance, and we are casually seeing how things play out. So far it’s been great. We really enjoy each other’s company and it really seems like things are brewing once again.

But as we get closer, this past issue of “not being chosen” is rearing its ugly head again and infuriating me, even though I had stopped caring about it long ago. Part of me wants to tell him he had his chance and blew it. The other part of me realizes that sometimes things don’t happen in the timeline you want them to, and that they happen when they’re supposed to happen.
I’d like to be able to forget the past and focus on what’s ahead, but I can’t shake it. What do you think? Is it best to forgive and let go of the past and take the opportunity, which could genuinely lead to something? Or is this gnawing feeling there to tell me something?

– Stuck in the Past, Boston