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Should I tell my friend how I feel — before her wedding?

‘I’m fully aware this is for my benefit, not hers’

Love Letters

Love Letters

Q. I’m a 30-year-old man who has a female friend who used to be a fling. She’s getting married in a year, and I’d like some advice about whether I should share my feelings with her before then.

Backstory: We met through mutual friends years ago and immediately clicked. Talked the whole night, went on an actual date (which is still the best date I’ve ever been on), went on a few more dates, hung out with our mutual friends, etc. We both had busy schedules and work travel so the relationship developed much slower than it should have. Looking back, I probably didn’t express my interest well enough, and I think that caused her to keep her guard up. After a few months, she moved across the country, and without speaking about it, we had one final date and both kind of assumed our fling was over. I think we were both scared to bring it up and face rejection from the other.

A few months after that, I was in her city for work and texted her to catch up. We had an incredible time. At the end of the night, she finally revealed to me that she’d started seeing someone else — her current fiance. I was crushed, more than I expected to be. We’ve stayed in close touch in the years since, with the same electric chemistry but also a really positive, caring friendship that’s developed. There have been a number of times I thought things had a chance to start up again, but didn’t want to be the homewrecker, and instead let her relationship status do the talking. I’ve read enough of your letters to know that a “friend” you’re pining after and want more from isn’t just a “friend” — you need to tell them the truth and/or move on. But I think this has developed into something different.


Yes, if she dropped everything and wanted to start a relationship with me I’d strongly consider it. But after years of processing this and going on dates with great women I wished were more like her, I’m also finally at peace with the fact that she won’t, that she’s getting married to an awesome guy, and that I will (God willing) someday marry an awesome woman who isn’t her.


It took me a long time to get to this point, partially because I’ve heard from mutual friends that my feelings are reciprocated. But I do mean it very genuinely. So why say anything at all? I’m not planning some sort of dramatic speech — I just want to tell my friend how I feel about her. How hard it was to hear that she was seeing someone else, how strongly I felt about her back then, how grateful I am that we stayed in each other’s lives, how my feelings for her will always be difficult to explain, and, most importantly, how happy I am for her and where our friendship is today.

Also — I’m fully aware this is for my benefit, not hers. So do I owe it to myself to say something? And if yes, when and how? She and I also still live across the country from each other, so I don’t get to see her too often these days (though I am invited to the wedding).


AT PEACE IN PORTLAND (I’ve always wanted to write one of those names)

A. “At Peace in Portland” is a great name. I’ll admit that I get frustrated when people sign their letters “Confused” — because aren’t we all?

My advice: Do not to tell her before the wedding ... unless you happen to be having some deep conversation and she asks about your feelings. Don’t seek out time for a big talk. Telling her before the wedding makes it sound like a call to action — that you want her to consider you one last time before getting married. If you’re being honest about not wanting to get in the way of her relationship, let her stay on her path without hearing more.

Her relationship status has done the talking. Your attitude and presence in her life have also sent a message. Also, your mutual friends have probably given her some perspective. I love when people want to be transparent about their feelings, but this is the rare time when it’s best to stay quiet.

You ask whether you “owe it to yourself” to get this closure. I think not — and I’m not sure it’ll bring you peace.

You do owe it to yourself to pretend you’re the main character in a movie. You’re the protagonist who watches his friend/love get engaged, and then starts his own adventure. That’s the interesting part. Get going.



Whether or not you acknowledge it, your motivation in contacting her again is [to let her] know you’ll be ready to jump into a relationship if things don’t work out in her marriage. If you consider her such a dear friend, leave her alone to focus on her marriage.



If you have to get your feelings out, write her a letter and bury it in a drawer, but this isn’t the time to tell her how you feel.


“You do owe it to yourself to pretend you’re the main character in a movie.” I disagree. He already believes he’s the main character in a movie, and that the main character always lives happily ever after with the woman of his dreams. My advice is to STOP PRETENDING to be a main character in a movie.


“I’d strongly consider it.” This is why she has moved on. After years of “electricity” you still cannot commit to a relationship with her. Keep your feelings to yourself and leave her alone.


Don’t have too much to drink at the wedding.


Send your own relationship and dating questions to loveletters@globe.com or fill out this form. Catch new episodes of Meredith Goldstein’s “Love Letters” podcast at loveletters.show or wherever you listen to podcasts. Column and comments are edited and reprinted from boston.com/loveletters.

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