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Dear Carolyn: My best friend has been trying unsuccessfully for over a year to date a girl who cares for him deeply as a friend but who I just don't believe is into him romantically. The situation is compounded by the fact that he can't bring himself to actually tell her he likes her.
I have tried to communicate this opinion as objectively as possible on multiple occasions to no avail. As luck would have it, I have been very attracted to this girl for many months, and I finally worked up the courage not only to tell my friend about this, but also ask the girl out.
He seemed relatively indifferent to my liking her but was hurt and surprised that I actually asked her out and that she agreed. I think the surprise is from his general belief that no girl uninterested in him could actually be interested in me. The date went really well; I think there could be a future there.
I know the damage is done and I hate that I have hurt him, but if the situation were reversed, I would be disappointed, but want him to go for it. Is there anything I can do (short of cutting the relationship off) that can heal our friendship? I feel like I am 15. I'm 26!
WORST. FRIEND. EVER.
Carolyn says: Uh, I think the surprise is from his general disbelief that you swooped in and stole his girl.
Granted, he's had over a year to act on his feelings, and he could have ridden something other than a glacier to accomplish the swooping himself. And, you told him what you were feeling and what you did about it. But still -- you told him after you asked her out; you didn't ask him how he'd feel about it first.
I think the flaw in your logic was in reversing the situation a bit too superficially (and self-servingly). You asked yourself, what if he asked her out knowing I liked her? When instead you needed to ask: If I liked her the way he likes her, and he knew it, and he knew I was paralyzed by her, how would I feel if he swooped in on her?
She was a very big deal to him.
But you knew that, and asked her out anyway. And I think you also know the way to heal things is to tell him truthfully that you'll stop seeing her as a gesture to the friendship -- but you don't want to do that. Which means we've pulled back the sheet here, haven't we? You kind of knew it was a choice between the girl and the friend, and you took the girl.
If you're regretting that choice, then tell him you'll stop seeing her. If it's a friendship worth saving, he'll refuse your offer; after all, he had a front-row seat to her lack of interest in him.
If you don't regret the choice, then you won't heal anything by pretending you do. Just say you're sorry you underestimated how much it would hurt him -- taking great care not to make it sound like "Sorry, sucker." That, after all, is your unspoken message right now.