Dear Dana: My Best Friend Just Admitted He’s In Love With Me

Dear Dana is a bi-weekly advice column for humans who engage in romantic relationships. Please send your dilemmas, issues, conundrums, assumptions, conflicts, anxieties, worriments, obstacles, complications, predicaments, queries, questions, and any other synonyms for “problems” to

Dear Dana,

I’ve been friends with this guy for over seven years. We get along famously, and often refer to each other as brother and sister. Because mutual friends have frequently suggested that he liked me more than a friend, I’ve had to ask him if this was true twice. Both times, in a polite but very serious tone, he would say “absolutely not.” It felt sincere, so I dropped it.

Well, two days ago, he professed his love for me. I’m still in complete shock. And his timing couldn’t have been worse: I’m just starting to come out of a cave after a huge breakup, I moved into a new apartment, and am trying to re-establish my independence. Years of considering him my brother has come to a screeching halt. I feel embarrassed, angry, and confused. 

I think he’s attractive, we have a friendship chemistry, but given our past and my current situation (just trying to figure out what I want out of life), I feel overwhelmed and need an outsider’s opinion.

So where do I go from here? Is it possible to salvage our friendship? Should I give dating him a try? I haven’t spoken to him since he dropped the bomb, but I know I need to address it soon. What should I do? 


Weirded Out


Dear Weirded Out,

If we were best friends, which, for the purposes of this column, I am fully going to pretend that we are, you would likely tell me this story while we sat at a bar and sipped bourbon-based cocktails. I would listen as you told me how flummoxed you are that this guy, your friend for the past seven years, just confessed his love to you. And when you were done laying out all of your anger and worry and embarrassment, I would ask you to pause. I would ask you to breathe. I would ask you to finish your drink and immediately order another. And then I would ask you to take a step back, forget that you’re you, forget that he’s him, and instead appreciate the fact that, as problems go, this one is pretty fantastic. A cute best friend type guy is in love with you. Your life is a romantic comedy. YOU’RE DOING IT RIGHT.

And we are not best friends, and I know nothing about you but these few paragraphs, but I like this guy. I think he’s good people. Because he waited until you emerged from your breakup cave to confess his feelings to you. He didn’t confess his feelings the night you broke up with the other guy, he didn’t try to kiss you while you were sitting on his couch and crying about your ex-boyfriend. He waited until you were through the breakup bullshit and ready to rejoin the world. That takes both hutzpah and patience and to find both characteristics in one guy who you are attracted to who is also your friend is good problems.

I know that you are very concerned about what this means for your friendship, what you should say to him, how long he’s felt this way, etc. But this entire situation boils down to one single question: Do you want a boyfriend right now?

I know that you just came up for air after a difficult breakup. I assume that you’re enjoying living on your own, not having to check-in with anyone else, and re-shaping your life exactly the way that you want it. And I understand that this is a truly awesome phase of life. It took me a few years to appreciate being single, but once I did I was unstoppable. To be newly single and happy is the just-stepped-into-a-hot-bubble-bath stage of life. You’re completely relaxed, you smell amazing, and everyone’s jealous of you. And if you don’t want to give that up just yet I completely understand.

But. If you do want a boyfriend, if you’re currently dating in search of a boyfriend, if a long-term romantic relationship is something that you want to experience in the near future, then I implore you to turn your head to the left and start making out with your friend.

I don’t know the intricacies of your situation. I don’t know whether you’re ready for another long-term relationship or if this guy is marriage material (i.e. the type of guy who will occasionally rub your feet when you’re tired and encourage you to say “fuck it” and buy those Burning Man tickets you’ve always wanted).

But what I do know is that this man is attuned to your emotional state and, if you want a long-term relationship, you should Go. For. It.

Will it ruin your friendship? Yes, in as much as you will never again be able to have your friendship as it was the moment just before he confessed his love, but that’s true whether you date this guy or not. And if you do date him, then you may end up happily in love with your friend which is, really, the total dream.

Despite the story we often see in the world, starting a new relationship is kind of the worst. I spent the afternoon after my third date with my now-husband alone in a Laundromat, crying and journaling furiously while my socks roasted in the over-heated dryer. We had only been on three dates but I knew that my now-husband was more than just someone I was dating. I knew then that if I made him my boyfriend he brought with him a complete future. When I looked at him I could see marriage, kids, endless weeknight dinners, Christmas mornings, and the thousands of small sacrifices we would make for each other.

The transition from being single to coupled is full of adrenaline and excitement, but some of us don’t like that flip-flop feeling in our tummy. Some of us prefer our feet on the ground. Love changes you and change is something most of us recoil from. Do you want this man to change you? Do you want to change him?

We’re back in the bar, you and I. We’re on our third drink. You tell me that you still haven’t spoken to this man since his confession and you don’t know what to do. You just don’t know. I tell you it really is simple: This man is your man if you will have him. And then I take your phone, dial his number, and hand it back to you, ringing. He answers. And you say what comes next.

Dana Norris once went on 71 internet dates, many of which you may read about here. She is the founder of Story Club and editor-in-chief of Story Club Magazine. She has been featured in McSweeney’s, Role Reboot, The Rumpus, and Tampa Review and she teaches at StoryStudio Chicago. You may find her on Twitter at @dananorris. 

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