Love Letters

Can he reach out to a married ex?

Q. About 14 years ago I made a decision between two women. I had feelings for both of them and they had mutual feelings for me, as well. I ultimately made my decision and I believe it was the wrong one. I was married for almost 10 years and I am now divorced. I think of this other woman on a daily basis even though I have not spoken to or see her in almost 14 years. She lives in the same town as me, and I know through Facebook that she is married now. I am tempted to write a letter to this woman and just tell her that 14 years ago I should have pursued a relationship with her. I know it sounds crazy but I think somehow I am in love with her. I almost need closure because I cannot get over her. I just want to write this letter and tell her how she made me feel so long ago and express that I think she is a great person and hope she is happy in her life. Is this a bad idea? Please offer some advice. Thank you.

Past Regret, Boston

A. You’re not in love with this woman. You’re just lonely and sad about your divorce.


You’ve turned this ex into some mythical soul mate who can magically fix your life, but in reality, she’s just an old crush. Had you chosen her back then, you might have dumped her after a few months. Don’t make up a crazy narrative about the path you didn’t take. You’re just inventing fairy tales.

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You are not allowed to write a love letter to a married woman. It’d be one thing if you just wanted to say hello, but you’ve admitted that you want her back. Your intentions are all wrong, and I will not endorse any form of communication.

Use your energy to meet new people. It’s a big world. Go explore.



Leave it alone. You’re dreaming.



Oh, just stop it. You will probably tick her off. “Hey, remember me? I rejected you 14 years ago in favor of another woman? Oopsky.”


You’re not in love with her. And you shouldn’t confess your love for a married woman . . . especially one you haven’t seen in 14 years. I am very different than 14 years ago. The guy I was in a relationship with back then probably wouldn’t be a good fit for me now. . . . We’ve both changed.



NOOOOOOO! There is no way you should contact this woman. She is by all intents and purposes a happily married woman. This is your issue, not hers. I agree with Meredith that you’re not in love with her. You’re in love with the thought of what might have been. Straighten your life out, then go find someone who is single.


Mere’s advice is right on. You’re head is all messed up right now and you’ve built this all up. Don’t create a messy situation.


On further thought, contact her. Tell her your deepest longings for her, how she is your soul-mate, the one that completes you. She will then realize her true love, dump her husband, abandon the kids, and run off with you to lead a life of bliss and contentment.


Dear letter writer, allow me to rephrase your letter: “Dear Mere, I’m miserable. Am I allowed to make other people miserable, too? Thanks, A Moron”


Absolutely write the letter if you think it’ll help you. That’s supposed to be therapeutic and all. But do not send it. That would be a disaster.


You chose another woman over her. Now you want to come back and tell her how she made you feel way back when? Really? How do you suppose she will react to that? I’ll give you a hint: She probably wasn’t happy with your choice 14 years ago, and she won’t be thrilled to hear that “Oh, it should have been you that I chose.” Leave her alone and process your grief. When you are ready, start dating again (single women only, please).


This should have been one of those letters that you write, and when you read it back to yourself you realize how ridiculous you sound. You don’t need to read what everyone is going to write today. Just take a step back, read the letter, and think.


I got a letter like this once. It made me think that the guy was a huge loser. Just sayin’.


I say write the letter. Be really poetic and apologize profusely so that she will feel bad for you but understand your plight. Then sneak up to her front window and watch as she reads the letter aloud to her husband and laughs so hard she falls face-first, open-mouthed into his lap. This is what a real relationship looks like.


How is it “wrong” to contact someone and relay their feelings? If it was truly wrong, then the woman will let him know that and move on. Who has the right to say what is right and wrong. She’s married? So what?


I don’t think it’s right to write a note admitting the desire to get back together. But there’s nothing wrong with an “I found you on Facebook and thought I’d say hello” note. Depending on the sincerity (and platonic tone) of the note, if she wants a friendship, then she’ll write back. If not, then she’ll ignore him. If it’s a love letter, then she’ll either be freaked out and still ignore him, or tell him to get over it but be flattered he still thinks about her. If it was two years ago, then my answer would be different. But it’s been 14 years. I’m sure she’ll be flattered.


I’ve been here before, and you know what I realized? This urge to reconnect with an old flame is just laziness. And fear. Meeting somebody new to connect with takes a lot of hard work and can be really scary.


I never comment on the actual letter, but this just happened to me recently and, boy, do I wish it had not. I held this guy in the highest esteem and thought of him fondly for 27 years. Then he contacted me as an item on his “bucket list” after he had gotten a bad diagnosis. Long story short, I no longer hold him in high esteem nor think fondly of him. Let her keep thinking fondly of you.


This column and reader comments are edited and reprinted from
Meredith Goldstein can be reached at mgoldstein@
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