How Do I Reject a Guy Without Seeming Mean? Ask a Pro


Hey Head Pro,

So I’m your typical mid-twenties female living in NYC – I live in Murray Hill, I have a decent job, a solid group of friends and am generally pretty busy. I’m not one of those “I’m too busy for a boyfriend” types, but I don’t really pursue guys I have lukewarm feelings for. I’d just rather hang out with my friends during the little free time I have.

That being said, I recently hooked up with a guy I have known since college. Although we don’t hang out often, one night we were out with mutual friends, we were pretty wasted and we ended up making out and cuddling. I don’t think much of it, but its not really something I want to happen again. Unfortunately, I think he may like me, because he is constantly texting/snapchatting me asking me how my day is, if I can hang out etc. I hung out with him one time afterwards for coffee, confirmed that i’m uninterested and paid my share to make coffee seem less date-ish. The next morning, he both snapchatted me asking me to hang out, then followed up with a text – both of which I ignored. He then contacted me again in the middle of the week, although I told him I’m traveling for work and am trying to focus.

Although I am flattered, because this is all a nice gesture, I gave it a chance and am not into him. How do I get my point across without being a total bitch?


Cannot handle any more awkward text flirts

Unfortunately, there’s no real way to do this without coming across as at least a little mean. Like, you don’t have to be a COMPLETE bitch about it and say that his voice is what you imagine it sounds like when Donald Trump pulls back his foreskin, but there’s no nice way to tell someone that you don’t like them in a romantic way.

That said, you’ll make this a lot more painful than it needs to be if you try to employ the “fade out” method where you just kind of grow more and more distant. You could go the direct route, where you tell him kindly but firmly that while you had a nice time and it’s nothing personal, you aren’t feeling him like that. He could say “thanks for being honest,” which exactly zero guys have actually said upon being rejected. He could also react badly, but at least not seeing him often will probably limit his retaliation to sad, angry MRA-style rants about women being bitches, or something.

Of course, he may not be nearly as into you as you think, and was just kind of happy to have someone to connect with in the shitty antfarm that is NYC. If you don’t want to go the direct route, you can always continue to ignore his messages — most guys will get the hint sooner rather than later. And like, if it’s really that annoying, you can always remove him from your snapchat and pull a “new phone who dis?” when he texts. Like I said, provided you aren’t openly and outwardly malicious, you’ll come off about as well as anyone can reasonably expect in this situation.

Dear Head Pro,

I am in love with this guy. The shit part is that he is my best friend. I’m not talking flirty, just met a year ago “best guy friend.” I’m talking his mom is practically my mom, know everything about him, chill out on the couch and watch Star Wars for 4 hours best friend. All of my friends think he is a huge fuckboy, and I kind of agree, but I’ve known him since I can remember and he is definitely not like that, it’s just some stupid act he puts on. He seems like your typical hot high school athlete. I always had a tiny crush on him, but this year I realized that I actually love him. I don’t think he is aware of any of my romantic feelings whatsoever, and I doubt he would ever feel the same way about me. He treats me like his sister. I just got back from 4 months away from home, and now he seems to pay way more attention to me, and I don’t know if it’s just me, but he seems to be a little flirty. He is kind of touchy, and always seems to keep the conversation going when we text. Which is also shitty because it just makes me want him even more.

And to make this whole situation 10 times worse, he has a girlfriend who he’s been with since the late fall. She is pretty annoying, and just cares about her appearance. She’s nice and all but it seems like they just settled for each other. She’s kind of this fluffy braindead unicorn if I must make an analogy. I have been thinking about professing my love to him in the whole My Best Friends Wedding kind of way, but A) I don’t have the balls B) I feel like it is hopeless given that he has a girlfriend and most important C) If he doesn’t feel the same way, it would probably destroy our friendship. I hate not being able to have him and secretly wanting him. What the hell do I do? Do I tell him and risk our friendship- or do I just ride it out and have nothing happen? I feel like when I’m an old fuck sitting in my rocking chair I am going to regret not telling him about my feelings. Help!

P.S- I would ask my friends for advice but it would be kind of embarrassing to admit my feelings about him since I tell them all he’s basically my brother.


Cowardly, indecisive, kind of friend zoned Betch

One thing I think you probably have to understand is that everyone around you — your friends, your parents, etc. — know EXACTLY how you feel about him, and probably wish the two of you would just get on with it already. Like, not to undermine the authenticity of your friendship, but teenagers hide their feelings about as well as Kanye hides the Funions when Kim’s preggers. If he’s a highschool fuckboy but sweet and caring around you, I promise you’re not the only one to notice that. So, like, don’t feel like you can’t talk to people about it, or that you’re carrying around some burdensome secret.

You should also do some soul-searching and ask yourself: Do you REALLY hate that you “can’t have him,” or is that lust-boner a big part of your feelings for him? I mean, you’ve known him your whole life, so what’s changed? Like, he gets a girlfriend, and all of a sudden you magically go from thinking he’s a cool guy to be around to being madly in love with him? I’m not sure I buy that. I mean your feelings are what they are and I’m not trying to tell you how you feel, but experience tells me that at least part of this is a result of your transition into adulthood and the accompanying adult relationships.

My advice: When his relationship eventually ends (and it will!) and you still feel what you feel, lay it on thick. Like, get really touchy, flirty, etc. If he’s feeling something similar, he’ll respond like a dowsing rod because teenage boys are basically 98% hormones. But if the feelings magically subside once he’s no longer spoken for, you’ll be glad you didn’t profess your love to your Star Wars buddy.

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