How Do I Friendzone Someone & Actually Stay Friends?

Q: I have a friend from college I’ve reconnected with since moving to the city, but it’s becoming increasingly obvious that he has feelings for me beyond friendship. He’s kind and smart, but there are no feelings of that sort on my end, nor have I ever entertained his hints of affection. If I’m being honest, a lot of his feelings seem less like he actually likes *me,* and more that he’s desperate not to be single anymore after a tough breakup last year, as he constantly vents to me about how hopeless he feels in the New York dating scene. I’m not one to cut out friends, but the tension (on his end) and the discomfort (on my end) is getting to be a bit much. Any advice on how to make my lack of feelings more clear without crushing him? — Eva*

A: Hi Eva! I was once in your exact shoes. I had a guy friend who seemed to have feelings for me. I tried to keep things firmly friendly, but life had other plans — I had a wardrobe malfunction in front of him at a romantic Italian spot, which only put a spotlight on our mismatched interests in each other. Sigh. I, too, felt that same mix of tension and discomfort, and I wasn’t sure if his crush was personal or if he was just sick of being single. I remember feeling so guilty, like it was my fault that I wasn’t interested in him beyond friendship, and like I was in the wrong for sparking a crush without managing his feelings more effectively. Years later, I see the dynamic differently. I want to walk you through some ideas for handling this situation — and I will. But first, I have some thoughts about what your friend is really doing here.

It’s kind of you to worry about cushioning his feelings. Is he treating your feelings with the same respect? It doesn’t sound like it. The way you describe it, it seems like either he’s oblivious or he knows that you’re not interested and is plowing ahead with these “hints of affection” anyway. If it’s the latter, you’re sending out red lights and he’s putting his foot on the gas. That’s not fair to you.

Women are socialized to smooth over awkward situations. For a lot of us, it’s second nature to receive a cannonball of blurred lines like this and try to fix it. But this is not our responsibility. You’ve already responded stonily to his hints, which is the perfect way to handle unwanted affection. You’ve already listened to his dating woes. You’re even writing into an advice column now for extra help. At a certain point, it’s on him to pick up on your cues.

I do feel for your friend. New York’s dating scene veers between overwhelming and isolating, and getting back out there after a tough breakup truly sucks. There’s this awful cycle that people can easily get caught in: They feel lonely, so they date to fill a void instead of putting their best selves out there. Then, when dating goes badly, they feel even worse. This repeats until they get to a sad, spiky, despairing place where it just doesn’t feel fair that they’re single. At that point, they either give up on dating or start acting like a total nightmare (or both). I say this with no judgment because I’ve been there.

But this is a city of 8 million people. Your friend will absolutely meet someone who goes bananas for him, as long as he puts in time and effort, and — this is key — shifts his mindset. Nobody owes him affection. It has to come organically. If you sensed that he truly had a major crush on you, specifically, and not just a desperate desire to avoid singlehood, I’d have more sympathy. But we’re all adults here. It’s time for him to behave like a real friend to you. If he can’t, it’s on him to walk away.

The next time you see this friend, you could talk about what an amazing time you’ve been having getting to know someone new. Of course, maybe there’s nobody you’re genuinely excited about, and I understand if you don’t want to lie to him. Still, though, I’d hope that if you mention seeing other people here and there (or at least wanting to), he’d get the hint and back down. You don’t need to deliver a full Broadway monologue about how hot you find some random guy on Hinge. But if he asks to hang out on Friday night, you can respond, “I have a date planned. How’s Saturday instead?”

Typically, when you’re at an impasse with someone, it’s worth having a tough but honest conversation about it. I don’t think that’s the right move here. When it comes down to it, you’re just not attracted to him, right? Telling him that is unnecessary, unless you really feel like it’s the only option you have. It’ll only embarrass him, and it’s not helpful feedback because there’s nothing he can do about it.

Hopefully, after you emphasize your interest in dating other people, your friend lightens up on you. If not, it’s OK to let this friendship drift away. It might not be serving either of you any longer.

*Name has been changed.

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