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I read a letter from his ex

It was from a few years ago

Love Letters

Love Letters

Q. My boyfriend and I are in our mid and late 20s. He’s the best person I know; he’s hard-working, a family guy, smart, funny, and a gentleman. We’ve been together a little over half a year, but have been dating for almost a year in total.

Before he met me there was a woman he chased for almost seven years — until last January. They were dating when he was younger, had a bad breakup, and even if he dated other girls, he would drop every relationship if he felt he had a chance to be with her again. Their dynamic was toxic and on-and-off until they decided to part ways.


He has never made me doubt him since we made things official. I think it’s normal for me to assume that he still thinks of her because she was in his life for so long; it’s impossible to shut those feelings off. The thing is, he was cleaning in his room and throwing things away. That’s when I saw him throwing out this envelope — and I knew it was from her. I freaked out because I thought it was recent, so I couldn’t help but open it without him noticing. It said something like “we have to be apart to know if we should be together again.” It was from just a few years ago.

I’m not worried about the fact that he kept the letter because he kept all types of random stuff from random people and threw it away. But I am concerned about the possibility that he still is subconsciously on this “master plan” of “let’s part ways to reunite one day” with her — and that I’m just a chapter in his life. Again, he hasn’t made me feel that way, but he’s human and I know we don’t forget people that quickly. He really did love her.


I know it sounds drastic, but I’m so concerned about this that I’m thinking about ending the relationship now rather than having it end in heartbreak because she is “the love of his life.” My friends say I’m overreacting and that I should trust he’s really happy with me — that he would never want to get back with her now that he’s in a healthy relationship. But that sounds too good to be true. I don’t mind admitting to him that I opened the letter. But I want to know: Should I talk to him about this overall? If so, how? And what things should I look out for in the way he responds?


A. Let the whole thing go, and do not talk to him about the letter.

A lot of people say “someday we will reunite...” when they’re sad about a breakup. Your boyfriend treated the letter like garbage because he didn’t think of it as a contract.

The upsetting reality is that there are many reasons you and this great guy could eventually break up. There are also a bunch of paths that would have you stay together. The possibilities for your future are endless. How upsetting, right? If only you could predict the future!

It would be easier if there were one threat — this woman — and you could wipe that issue off the board with a conversation. But it’s not that simple, and I’m not sure there’s anything your boyfriend could say to make you feel better, other than what you already know, which is that he ended it a year ago. There are no tells that would help you figure out whether he still loves her. It’s not as though he’d blink three times and reveal he’s going to meet up with her in another year.


Let this relationship play out and accept that there’s no master plan. After another six months with him, you might be ready to move on for reasons you can’t anticipate. If you try to guess the ending here, you might cause one. It’s better to enjoy what you have, trust your gut (which is telling you he’s into you), and be present in the moment. Accept that the letter made you feel uncomfortable and discomfort is part of life.

Do not ask him to give you a big speech to let you know the letter is no longer relevant. Again, you watched him throw it way. Do the same in your brain.



You’re being paranoid. You and your boyfriend have been together for six months to a year and the letter was from “a few years ago.” If you want to set a fire in your relationship, sure, ask your boyfriend about it. Otherwise, pretend you never saw it and have some confidence in yourself and the relationship.


Based on your description, they were apart many times before he started dating you. While there are no guarantees, it seems like they have decided they aren’t going to be together. You need to let this go and deal with your insecurities (which existed before you read the letter, and probably before you dated him) or they will eat you alive.



What you need to get rid of is this thought because you are wrong that “it’s impossible to shut those feelings off.” It’s not impossible. You simply don’t feel them anymore. He’s with you now, not her, and not in touch with her. What you are worried about is a giant nothing burger.


The big problem here is not his attachment to an ex. It’s your attachment to him. It’s shaky. You’re insecure. You’re digging things out of the trash to make yourself doubt him. If you want to stay, you have to stop doing that.


A rare moment when we all will say, “your friends are right!


Sometimes I miss being in my 20s until I read letters like this.


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