Dear Addy: I’m in Love with My Closest Friend

Dear Addy:

I am completely, totally, head-over-heels in love with one of my closest friends, a fellow graduate student at UMass. I have known her for several years and I know we are perfect for one another, two hearts beating as one. I want to marry her and spend the rest of my life with her more than I’ve ever wanted anything (with the possible exception of tenure). I’ve brought two of our mutual friends into the vault, and they’re split on what I should do — one says I should definitely tell her, the other says I should give it some time.  Usually, I’m a cautious person, but I don’t know how much longer I can wait. The trouble is, we live together, and I don’t want things to be awkward. What do you think I should do?


Two Hearts Beating as One

Dear Two Hearts:

Bear with me while I tell you a story. Many years ago, a friend, roommate, and fellow graduate student declared his love for me by a) calling me 23 times in one hour (I was at school, studying for a final exam later that day) b) sneaking into my bedroom and leaving roses on my bed and c) insisting that we were perfect for one another and needed to be in a romantic relationship, immediately.

You’ll be shocked to hear that it didn’t work out for us romantically. We never dated. That night, our other roommates took him out to the bar to drown his sorrows in whatever it is that STEM students drink. For the rest of the year, he and I awkwardly skirted his confessed love and never discussed it again. (Yes, I am passive-aggressive, but that is not the point.) I share this story only to say: you may want to use caution.

That said, I have another story, a story of two dear friends, who lived together in a house for a year.  At the end of the year, Friend A was planning to move out and away, in the interest of taking a job as a community organizer in Appalachia. Eleven months into the living arrangement, Friend B boldly asserted to Friend A you can’t go to Kentucky, I’m in love with you.

Friend A went to Kentucky, but not before marrying Friend B, who went with her. They’ve since moved back to idyllic western Massachusetts, had a couple of children, and are still happily married.

The moral of this story: you don’t know what will happen, and neither do I. And at the risk of being a killjoy, I have to say: while it’s possible that things will go swimmingly for you, it’s equally likely that they won’t.

It must be said: I’m a romantic. I appreciate bold declarations and grand gestures, even when they’re borderline psychotic, which explains the better part of my own relationship history. That said, not everyone is comfortable with that kind of action. And at the end of the day, you don’t know how she’ll react. She might already know. She might not be sure of her feelings. And maybe, if you’re lucky, she might love you non-platonically in return.

Now, I am a firm believer in discretion in all matters, including matters of the heart (although I seldom exercise it myself). But by discretion, I don’t mean that you should refrain from action. On the contrary, you must assess your feelings, your motives, and the situation overall. If the feelings are real (and it sounds like they are), you must act.

If you’re sure of how you feel and convinced that you can’t spend another second of your life without sharing your feelings, you owe it to yourself (and to her, and to the friends you’ve dragged into your drama) to tell her.


You have to be prepared for the possibility that by declaring your love, you’ll humiliate yourself and lose a friend in the process. That this will all blow up in your face, because it might.

But if you’re really convinced she’s The One, declare your love! You might end up happily married in Appalachia (figuratively speaking). Even if you don’t, things will work out for you, I promise.

The roommate who professed his love for me? He’s still my friend. He (we) got over it. And three (short) years later, he’s happily engaged. His fiancee? Another UMass grad student, far lovelier than I am.

So tell her! And let me know how it goes.




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