My Friend Is Upset That I’m Dating His Brother. Is Our Friendship Doomed?

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Welcome to Tough Love. We’re answering your questions about dating, breakups, and everything in between. Our advice giver is Blair Braverman, dogsled racer and author of Small Game and Welcome to the Goddamn Ice Cube. Have a question of your own? Write to us at toughlove@outsideinc.com.


This question is a tiny bit about a boyfriend, but mostly about how to repair a friendship.

Fifteen years ago, I moved to New York City for a job. I became good friends with someone I knew casually in grad school, and eventually good friends with his husband, too. The three of us shared a bond because of our intense jobs in a big city, our midwestern roots, and complicated issues with our families. The last point is sort of the crux of this issue.

The friend and I both come from skiing families, and ski really well together; our friendship has helped foster my continued love of skiing and winters even while living in New York. His husband doesn’t ski, so it’s always been “our thing,” and I know he feels the same way. About ten years ago he planned a ski trip for a group of friends, including his younger brother. His brother and I also became very good friends. This spring, we finally admitted what was thuddingly obvious to everybody—except apparently my friend—which is that we’re seeing each other.

My friend’s brother—that is, my boyfriend—is sweet, graceful, and kind, and I care a lot about him; this relationship was a very long time coming. Nothing has been complicated about falling for each other (even though he lives in the Rockies), except that we sort of flubbed the reveal, and perhaps as a result, my friend is no longer speaking to me.

This hurts. My boyfriend and I knew this would be weird for everyone and are doing our best to be low-key, but I wasn’t expecting an immediate and total ejection from my own social circle, and for my friend to be unwilling to continue our friendship. This is a friendship that has meant so much to me—and I thought to him, too. I’m not a scorched-earth kind of person, and in any case, he’s my boyfriend’s brother, so I also don’t want to start a fight.

I’m not even sure what the right question is. A while ago, I thought it might be: How do you convince a friend who is a fellow black sheep that you still care about them, when you also care about someone else who blends easily into the family herd? Months in, I’m afraid the question I need an answer to is: How do you grieve a friendship with your first adventure buddy, who introduced you to your boyfriend and helped you keep skiing for a long time, even after he turns out to have kind of been a real jerk?

First off, congratulations on your new relationship! I’m happy you found someone who matches you so well; that’s always something to be celebrated, even when the situation is complicated.

Reading your letter, I think I see what may be a fundamental misunderstanding between you and your friend—although whether it’s fixable, I can’t say. You feel betrayed by him because it’s unthinkable that he would turn away from you, even abandon you, when you thought your friendship meant so much. However, it seems that it’s precisely because your friendship means so much that he feels so betrayed about your lack of transparency. If he was the only one who didn’t realize you were dating his brother, it doesn’t necessarily mean he’s oblivious. It might mean that he cares about you so deeply that he didn’t believe you would keep something like that a secret from him—particularly because you know about his fraught relationship with his family and how this might affect him. It means he trusted you to be honest, and now he feels foolish, or even like you made a fool of him.

He may have been a real jerk—but he feels like you were a jerk to him, too. And even if the flubbed reveal was a complete accident, it probably rubbed salt in the wound. Oftentimes, the way tough information is revealed—through honest communication versus an accidental discovery—makes a huge difference in people’s ability to adjust, rebuild trust, and move forward.

It’s too late to redo the reveal, but I think it’s worth trying one more time to get things on the right page. Even if it doesn’t rebuild your friendship, it’s a way of honoring how much it’s meant to you over the past decade and a half. You might try asking for one final conversation, or, if it’s easier, writing your feelings in a letter. Take some time to reflect on why you didn’t tell your friend that you were dating his brother. Were you scared of something going wrong? In denial? Did you tell yourself it didn’t matter? Don’t focus on coming up with the most sympathetic story; people can tell when you’re saying what you think they want to hear, and his radar is especially attuned right now. Instead, be as vulnerable and truthful as you can. Apologize sincerely for hurting him. Express the ways that you wish you had acted differently, and how you would do things differently in the future. Ask if there’s anything you can do to make things right.

It’s one thing to tell your friend how much you value him, and something else to show him by making yourself vulnerable. It’s possible that he’ll take this opportunity to reject you again, but I still think it’s the right thing to do.

Then, let it go. He’ll reach out to you or he won’t. Your mutual friends will forgive you or they won’t. At this point it’s not under your control.

If he chooses not to reconnect with you, it will hurt, just as it does now. You’ll grieve, and grief takes time. There’s no shortcut. Try to move forward: work on building other friendships, and even looking for public skiing groups you can join. Nourish your current relationship, and take the time to be present and enjoy it. Maybe you’ll end up reconnecting with your friend in the future, and maybe not. It’s up to him and his comfort level. But you can focus on the people in your life, the ones who’ve stuck around. Take care of those relationships—not just for now, but for the future.


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