Guest post! “How do I break up with someone right after agreeing to go out with them?” (#131)

video color bars with the words "No Signal"
Image courtesy of adlologger on DeviantArt

Good news, everyone, we’ve got SexyTypewriter here to teach another reader about the Art of No. If you like hilarious smart people (and I think you do) and if the dating pool sometimes feels like a greenish, swampy, shallow place (and I think it does), read her fantastic blog. She will forever go down in history as the person who introduced me to the phrase “dangly man-pudding.”

Dear Captain Awkward,

How do I break up with someone right after agreeing to go out with them?

I have become close friends with a guy I have a class with.  He is a psychology and philosophy major and so we have really deep, intimate, and interesting conversations.  Over the course of several months, he developed a romantic interest in me. Two days ago, completely out of the blue, he asks me if I would consider dating him.  Unfortunately I have a terrible habit of speaking without thinking, and I just said “yes” because it was easy and I knew it would make him happy.

However, when I reflect further about my decision, I don’t think I should have agreed.  I have really interesting conversations with this guy and he is a genuinely kind and good person, but I am not physically attracted to him in the least.  And the physical aspects of a relationship are important to me.

I know that all the blame in this situation falls on me, for encouraging the interest with the intimate conversations and for agreeing to go out with him, and I feel really guilty.  I want to get out of this situation yet do the least amount of harm to this guy.  Theoretically, I feel like this should be easy to do because we’ve been dating a whopping two days, but it feels really hard.  I also feel dumb because I am passing up an opportunity with a great guy who will treat me super well just because I’m not attracted to him.  But I can’t think of a way be satisfied in a relationship when there isn’t chemistry.  Can you help me?

Thank you!


Dear Cat,

Ah, yes. That old song and dance. Boy meets girl. Boy likes girl. Boy asks girl to be his girlfriend. Girl merely likes boy as a friend, but agrees because she’s too stunned, flattered, guilty or socially programmed to say anything but yes. Boy clicks his heels and pumps his fists and changes his relationship status and sees Han Solo in car window reflections. Girl feels like an absolute turd.

It is a tale as old as time!

You clearly think highly of this gentleman, but if the chemistry isn’t there for you, it isn’t there. You are not being shallow in thinking that that aspect of a relationship is super important. And you can’t force physical or sexual attraction. That said, attraction can grow (or pop up out of nowhere on particularly fateful nights featuring epic drinking), but that is something that should be explored within the context of a friendship and not a relationship.

There’s no way that there won’t be hurt feelings here, but you owe it to the guy and to yourself to extricate yourself from this sham of a couple as soon as possible.

Talk to him privately in person (yep, face-to-face human contact) and gently let him know that you would prefer to just remain friends. You like him and you like hanging out with him, but there really isn’t a spark happening on your end. He sounds like an A1 guy. He deserves a girl who wants to tear all of his goddamn clothes off with her teeth. You know?

Now, in order to avoid future mix-ups, hurts and unwanted relationships, let’s do a little exercise here. I’m going to ask you a bunch of questions, and you are going to respond with this great phrase I love using. It is a phrase that you should get in the habit of using, too. That phrase is “No, but thanks!”

Q: Can I buy you a drink?

A: No, but thanks!

Q: Would you like to go out sometime?

A: No, but thanks!

Q: Wanna be my girlfriend or whatever?

A: No, but thanks!

Sometimes, you can simplify by deleting the “but thanks” and keeping only the “no.”

Q: Can I come home with you?

A: No.

Q: Come on!

A: No.

Q: What are you, a virgin? A prude?

A: Maybe. No.

Q: Would you take on this project on while I take a two-hour lunch break?

A: No.

Q: Can I borrow fifty bucks?

A: No.

Q: Can we do it without a condom this time?

A: No. (This one also warrants an “oh hell no.”)

No is a beautiful, magical and criminally underused word. Please learn how to use “no” without ever feeling weird or guilty. It is power.

28 thoughts on “Guest post! “How do I break up with someone right after agreeing to go out with them?” (#131)

  1. Oh yeah, I know this story. Been there, done this, have many T-shirts, ran away screaming after 2-3 dates when I couldn’t stomach the kissing. It’s especially awkward when everyone on the planet will tell you to give him a chance and you’ll change your mind. I have never managed to do that. (Meanwhile, my mom who told me that I should always give the guy a chance regardless of my lack of attraction? Is now a widow who is not enjoying “give him a chance” dating at all. Hah.)

    Captain, do you have any tips for when this goes the route of “Give me a chaaaance!” (note: I got that one all the damn time, for like 20 minutes of arguing) or if the guy starts to get crazy on you? It’s kind of hard enough to no a guy in the first place even when he’s not giving you very good arguments or giving you the willies.

    1. There’s some stuff in here that might help you.

      If you break up with someone, or say “no,” and get the “give me a chaaaaaaaaance” or the angry response (but you SAID you would GO OUT WITH ME and now you are JUST LIKE ALL WOMEN)…

      Take that as a giant, flashing sign that your “no” was the right decision. No chance!

      So you may say something like “Sorry, I know you are disappointed, but I need to shut this conversation down. You have my answer” and then get out of there.

      Quoting Gavin de Becker – “If you say ‘no’ and the other person keeps talking, ask yourself, why is this person trying to manipulate me?

      I’m big on saying no once and meaning it, and then not engaging with the conversation anymore. If you say “no” and the other person keeps trying to convince you, it’s a sign that they didn’t hear your no, or they don’t believe it, and they don’t understand boundaries, and any further relationship with them is going to be bad news. So if you have to keep repeating the no, it’s going to be a bit weaker every time. Down that road lies coercion, in your case, assisted by your mom. So you can also tell her “Whatever, mom, I need you to stop pressuring me to go out with people I don’t want to go out with and back me up when I say ‘no’.”

      I was so glad to see this letter come in after all of the “How do I seduce women or get out of the friend zone?” stuff, because this is what happens when you “convince” someone to go out with you who doesn’t enthusiastically want to be going out with you.

      1. “Take that as a giant, flashing sign that your “no” was the right decision.”

        So fucking true. My last ex tried to whine and cajole and beg me back into a relationship with him, in between telling me what a bitch I was being because he’s such a Nice Guy!! and never stole from me, killed a member of my family, or raped me (actual defense used by him). Before I wised up and cut off all contact with him entirely I even told him at one point that with how he’d been treating me, why on earth would I want to get back together with him, and why should I believe he really wants me back when he keeps telling me what a horrible person I am? It flew right over his head.

      2. Thank you very much.

        I finally, eventually, learned to not say yes by default, but it’s still awkward as hell. Like the one time I was literally trapped on a bus next to the dude for fifty long minutes and he wouldn’t stop harassing me for a date (and I actually had a boyfriend to cite as a reason not to date him!) until we got off the bus. Gah. Now it’s time for Mom to learn that lesson…muahahahahah.

      3. Aside from the manipulation aspect, everyone needs to learn that they don’t actually want to know. They don’t want to know. They don’t want to hear that they are unattractive, but they really don’t want to hear exactly why they are unattractive. And we should all know better than to demand that information from some harmless person whose only crime was to be attractive but not attracted.

    2. I think it’s actually much *easier* to say no to a guy who starts trying to argue your initial rejection (not including, of course, situations where the guy becomes aggressive or intimidating or what have you — which I think is a whole separate and difficult question for another time, because then it’s less about using your power and more about finding ways to avoid getting hurt).

      The initial rejection is hard because you have to recognize your own feelings (or lack thereof) for the guy, find a nice but clear way of saying no (assuming, as was the case for this LW, that it’s a good guy who you want to be friends with — if not, you can ignore the “nice” part), and overcome your feelings of guilt for rejecting him, and all often in a short span of time as is necessary when the topic gets sprung on you out of the blue one day.

      The follow-up no is easy because, as the Captain says, a person trying to argue you into being with them is a giant flashing sign of “YOU MADE THE RIGHT DECISION!” Assuming you gave someone a clear no, any follow up is absolute proof that they don’t respect your boundaries and that they’re less interested in having a mutually happy relationship/encounter/what have you than they’re interested in getting what they want. And if they push the subject more than one follow up question, then my desire to be nice in saying no totally evaporates, regardless of how much of a good guy they previously appeared to be.

      The best thing I learned from reading de Becker is that by engaging in 20 minutes of arguing, you’re actually sending a signal that the topic is still open for discussion and that prolonged pleading could change the outcome. It doesn’t matter how “good” his arguments are. Your no trumps them. So once you’ve said no, any argument is irrelevant and should be cut off:

      Dude: Will you go out with me/be my girlfriend/have a casual hookup?
      You: No, but thanks. I think you’re great, but I’m not interested in changing this friendship into something romantic/sexual.
      Dude: But why? We’re so great together! We have so much fun!
      You: I’m just not. Let’s talk about that class assignment.
      Dude: You should just give me a chance! I really think that we’d be great together/I like you so much/just this one time.
      You: I’ve said no. I’m not going to discuss this any more. If you want to go back to talking about that assignment, that’s fine. Otherwise, I’m leaving.

      Repeat as needed if he brings it up again. And if he really won’t let it go, think about whether this guy is someone you actually want to keep hanging out with, because anyone who tries to engage in 20 minutes of arguing about your no is probably not someone who is worth your time.

  2. Good lesson about “no.” However: Assuming that this guy does not pull a Jekyll and Hyde or a “just give me a chaaaaance” whine and is truly a nice guy with whom you have an intimate friendship, I think it could be good for you to just go out with him once and see what happens. If you still see dealbreakers, then do exactly what he did and come right out and say what you want: “sorry, not feeling it — friends?” Personally, I’d be less hurt if someone gave me one fair chance rather than changing her mind and saying “sorry, I thought it through and it’s never going to happen.”

    1. Do you really want to be in a “One Pity Date To Save Face” scenario with someone who is just trying to humor you? Doesn’t this lead to more “She gave me mixed signals, man” confusion and hurt down the road? Down that road also lies the 1,000,0000 “Why did you lead me on?” “If women would just SAY NO when they mean no, then we wouldn’t have to…” threads on the internet.

      I vote a strong no on this scenario. What’s going to magically happen on that one date that hasn’t happened before? Why is a woman thinking it over and saying “no” less believable after one chance? How is this different from “But just give me a chaaaaaaaance?” except more nicely expressed?

      1. Well, if in her mind it would honestly be a pity date, then yes, don’t pity him. But they have a great friendship and she enjoys spending time with him. I don’t think she would be spending the whole dinner or movie thinking “christ, I hope nobody sees me out with this loser.”

        I confess that while online dating, I’ve gotten interesting messages from women and declined to respond when I saw a photo. Isn’t it different when you know the person well IRL first?

        1. Tim, if they’re friends, they already spend time together! Enough time for her judgment call “Do I like him THAT way?” to be made. If she’s on the fence about it, or considering it, or curious about it, then go on one date, sure, maybe. Or just spend more time as friends and say nothing of it.

          Tim, I know you’re a good guy, and I know you don’t want to be advocating the whole “Ladies need to let guys down ‘gently'” thing up on my blog, but that’s what your initial post did. “Come on, what’s the harm in one date?” A lot of harm, if you don’t want to go on the date, and the people around you expect you to manage someone’s feelings to that degree.

          1. In fact dating is a rather unusual phenomenon, as seen by people outside North America: this whole event where one person has declared their interest and the other person is supposed to be considering their interest and maybe being open to persuasion. It’s not that we in Commonwealth countries are totally unfamiliar: it’s been imported for personal advertisements and online dating (since you need to do something with that person in order to actually meet them) and some people do it. But it’s not a cultural universal, this one-night-only opportunity to make your case as a romantic partner.

            The reason is that there’s not something magical about a date situation that causes people to show a whole new side of themselves, except possibly their very high pressure trying to impress side which is unflattering for a lot of people. (It’s a learned skill but most don’t get a lot of practice aside from occasional dates and job interviews.) If you’ve met the person and spent a bit of time talking to them, you probably have all the info that a date would give you in terms of liking them or not. If you weren’t aware they were attracted to you, you know when they ask you on a date. I can’t say for sure, but I get the impression that most people do not have a massive change in their initial inclinations going into the date.

          2. Thanks for your comment!

            It’s now making me think about Hollywood movies + all the terrible American reality dating shows we have, where dating is MAGIC! There is a makeover and some weird romantic trappings and prom dresses and jewelry and you already have Stockholm Syndrome from being trapped in the house with the other contestants away from everything about your life that makes you cool and interesting. It’s so artificial and weird, and yet so many people buy into it.

          3. I feel the same way about dating as Mary, but I never thought of it as an American/Not American thing (I’m Canadian), but rather as a queer/straight thing I’ve basically never participated in what I think of as the heterosexual dating ritual. All my relationships (regardless of the sex/gender of the other person) have basically taken the track of being friends, developing a crush, mentioning attraction/proposing sex, having sex, eventually sex turns in to a romantic relationship (or sometimes it doesn’t). Dating, as an activity you do to decide whether or not to be in a relationship with someone, seems very contrived to me.

          4. (I think she should say no since she’s well aware that it’s no–although I guess that, having agreed already, a coffee followed by a short polite no thanks would save this guy a lot of dignity. I don’t think she should go on a date to spend time with him. He’ll probably want a short time out.)

            But, hang on, do people really do that? It rings false to me. We’re not puffins. It’s not like the guy is all flutter flutter stomp dip BE MY MATE HAVE MY BABIES LIVE WITH ME FOREVER HERE I BRING YOU THIS CLEVERLY CONSTRUCTED KELP SCULPTURE AND A WEE TEDDY BEAR IN A TSHIRT THAT ALSO SAYS I LOVE YOU.

            The asking partner is offering further casual contact so that both people can determine whether even further contact would be unwanted, cool, or fucking wonderful. Or maybe all of the above at different times. They usually aren’t making a commitment themselves, or trying to make the most of this one chance to impress. It’s not so fraught.

            The scenario you’ve outlined above, where the male asker is Cyrano and the female askee is sketching cost-benefit analyses on the back of a cocktail napkin, is indeed weird–but I don’t know if it exists outside of movies. Bad movies. If you need to be persuaded rather than reassured, you probably shouldn’t be on the date.

          5. Mary, this is so true. I moved to Europe basically at the moment I became a grownup, and hearing my little brother talk about “dating” at his university back home in the States leaves me in a state of nonstop O_O face. It all sounds extremely stressful and artificial! I’m sure I’d be utterly hapless in that type of environment. My usual MO is to ask a guy I think might be interesting as either a friend or a romantic prospect to come out to a bar with a group of friends and just see what happens. “Dates” are what I do once in a relationship, you know, going out to dinner as a couple? Yeah. Dating = weird, I concur.

        2. But aren’t you doing kind of what the LW here is doing by deciding not to date a woman based on her photo? And I am not judging you at all; you are perfectly within your rights to make decisions like that and you owe no one explanations.
          But so is SHE.

          I mean, all this hullaballoo about “shallowness” is just baffling. So she rejects men based on their shoe color and he won’t date the Man Hands. SO WHAT? Firstly, IMO, we are allowed to have whatever bizarre (or regular!) preferences without having to defend them to the death to fragile egos at every turn. And secondly, if they really are that shallow to you, why would you want to date them? I’d be relieved to have dodged the bullet myself.

          (And Tim I am not really addressing YOU in that second paragraph, it’s just that this sort of springboards into a peeve of mine. I am not meaning to attack you or anything like that.)

    2. Having actually caved in and gone on many of these dates, I can tell you from my end that the guys TOTALLY thought I was into them just because I went. I’m as flirtatious as a rock, did not dress sexy, etc., but the guys were definitely “led on” by the fact that i went and “gave a chance.” It actually gets uglier when you have to tell them no after a date or two or three. And when they want to kiss, it’s not fun.

      And as Mary below pointed out: she does know the guy. His “date behavior” is not exactly likely to show her a whole new Hollywood movie side of him that will make her fall in love. She already likes him. Just not like THAT. She’s kind of “given him a chance” already just by hanging out with him platonically. She knows what she’s getting. And yes, some women do take ages to figure out if they like a dude or not, and “give him a chance” dating works for them. But it doesn’t for everyone, and we shouldn’t expect it to. It’s not fair to either party.

      Really, the only time “give him a chance” dating worked for me was when it was a blind date and I hadn’t met the dude beforehand to know for sure I didn’t like him like that. I’ve done that 3 times and it worked out twice. Number of dates where I already knew the guy and wasn’t interested and dated him anyway? Zero.

  3. LW, I think this is a wonderfully simple situation, because the way to say no gently is already the way you actually feel. You can say:

    “Sorry, I made a mistake. I think you’re great, but I really don’t feel attracted to you and I’m going to have to cancel our date. Sorry for messing you around.”

    or words to that effect, and really mean it. Your real feelings, that you can express with conviction because they are really true, are ALREADY one of the nicest possible ways to administer always-painful-no-matter-how-you-word-it rejection.

    This is one of those rare times when ‘tell the truth’ is all the advice you need, because the truth is you’re genuinely sorry for hurting him. And because SexyTypewriter and Captain Awkward have given you brilliant advice on how to go about telling the truth in the best way.

    As they’ve said, just tell the truth and be kind but firm, and you’ll have done everything that can be reasonably expected of you.

    1. Yes! Cat changed her mind. She is allowed to change her mind, and she is allowed to say, “I’m really sorry, but I’ve thought about it, and I’ve changed my mind,” without having to defend her choices.

  4. I can heartily second the advice here – you have to grit your teeth and do it because, believe me, the alternative is worse. If you let this go on, it could erode your friendship, your respect for your friend and your respect for yourself (based on my experience at least).

  5. The advice to consider switching from “No thanks” to plain “No” is spot on, too. I was having a problem a couple of years ago with people completely ignoring my “No, thank you!” and giving me that thing anyway. I learned to just say “no” deadpan, make eye contact, and then say “but thanks anyway!” when I knew they had heard the “no.” (And they only got the thanks if I thought they thought they were genuinely being nice or they were doing their job. Pushy? You just get the “no.”)

  6. I can heartily second the advice here – you have to grit your teeth and do it because, believe me, the alternative is worse. If you let this go on, it could erode your friendship, your respect for your friend and your respect for yourself

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