‘It turned into a year-long affair’

Former letter writers (especially recent COVID-era writers), please update us! Let me know what's happening by writing to [email protected] and putting "update" in the subject line.

Also, are you single? Coupled? Ready for a cold winter? Tell me your relationship issues and questions by filling out this form or by writing to [email protected]

Chat at 1 p.m.

Dear Meredith,

My high school boyfriend contacted me a little over a year ago while I was going through my divorce from a long marriage. We'd had no contact for over 25 years. We met to catch up as friends, but it turned into a year-long affair when he professed his love for me and I disclosed I still had feelings for him. I am not proud of what we did. We both felt guilty, but our feelings were too strong to stop.

Although he's not married, he's been engaged for a considerable amount of time, but they never had intentions of marrying. All of their finances are separate. She recently suspected his cheating, so we put the brakes on, and they are seeking counseling to see if they can repair the problems they are having within their relationship. I am not sure whether he will reveal our affair or his true feelings for me. I do believe he still loves her, which is why he is taking the time to do the counseling, at her request. He said he needs to figure out what he wants and wants to make sure he did what he could before he moved on.

My question is, what are the chances he will return to have the relationship with me we had before? It was perfect – except that he was attached. I feel like we were destined to be together if we both have feelings that remained so strong after over 25 years apart, and the timing that took place.

Any insight would be appreciated.

– Destiny


There’s no meant to be or destiny here. Only complicated, adrenaline-fueled feelings; an affair; and now, the aftermath. If I were you, I would not want him to return to you as he was. I'd want to be sure that he understands that you wouldn't want to be betrayed like this. If he leaves his parter and chooses to be with you, you'd want to know that he wouldn’t repeat his mistakes.

You say he and this woman weren't going to get married and that the finances were separate. All I'll say is that the organization of finances is not a big indicator of intention and commitment. If they didn't plan to get married, why were they still engaged at all? I imagine this woman would tell a very different story about her relationship.

It's very nice that you had feelings for each other after 25 years – I won't take that away from you. But the rest of your story is not aspirational. This man needs to figure out what happened to his primary relationship – how he wound up being so disloyal to someone so important. Then, if he decides to leave her and wants to return to you, you'd have to figure out why you're together and what expectations make sense right now. You don’t know what it's like to be together without barriers.

It would help if you stopped romanticizing the whole thing. There are real feelings here, but he spent an entire year not ending his engagement. That should give you pause. Over time, it might even make you angry. What you had before was messy. Long for something better.

– Meredith

Readers? Odds he'll return to the letter writer? What should the LW want right now? Keep pitchforks to a minimum, please; constructive advice is helpful.