
Hi Captain Awkward,
I have a slightly ludicrous ongoing awkward situation (more like an awkward dynamic) that I can’t seem to break free of. Here’s the thing: I’m 23, female, done with college, self-employed, I live by myself and go out a lot by myself because I enjoy it, and because all my really close friends live in other cities. The problem is that guys seem to see my solitary excursions as an open invitation to approach me. It’s not that I’m uninterested in dating someone, but somehow when I’m approached by guys in public my instinct is always “AVOID! ESCAPE!” even if they seem quite nice and aren’t creepy–I don’t really know why, something about being put on the spot, I guess, or a sort of feeling of preemptive sexual/romantic pressure since I feel like they are usually approaching me because they are interested in me sexually, not just as friends. I usually don’t feel this way when getting to know girls (even though I also date girls, and would slightly prefer a relationship with a woman), but they are also less likely to just approach out of the blue.
I am actually a really awkward and insecure person, but I’ve kind of compensated for it by becoming really charming and accommodating, so people always get the impression that I am super nice and absolutely enthralled with them when really all I want is to get away. You can probably see where this is going. Guy approaches me in public, I don’t like him or want to continue the interaction, but somehow I feel compelled to keep being nice, laughing at his jokes, accepting his invitation for coffee, giving him my phone number…pretty much as far as he pushes it, I go along with it. I can sometimes set boundaries, if the situation is extreme enough, but I am really bad at gracefully ending social interactions that are not blatantly harmful or creepy. I frequently give out fake phone numbers even when the guy is not being particularly pressure-y or persistent. I know this is a jerk move, but I really cannot seem to just say no. I try, and then the moment comes and I just find myself unable to do it.
Even more awkwardly, I now fear going to many of my favorite restaurants and hangouts because I imagine these guys lurking around where I last saw them, full of resentment towards me for stringing them along, giving no indication that I was anything but interested, and then giving them fake numbers and fleeing. I’m terrified I’m going to run into them again. In reality, they are probably not so numerous as to be able to from posses dedicated to hating me and staking out my favorite haunts, and I have hopefully not actually turned anyone into an MRA, but it’s getting kind of ridiculous. It’s also really standing in the way of getting out and meeting people (which I genuinely want to do). I don’t understand why even though I want to make new friends in my own city, I react so badly to people actually trying to meet me. Other people do not seem to really understand my predicament, as “getting hit on regularly by perfectly acceptable men, pretending to like them, and then acting like an asshole” is not particularly sympathetic behavior. I’m really hoping you have some insight to offer.
Thanks,
Deceptively Nice
Dear Deceptively Nice:
I think you might find some helpful stuff in “The Art of No” threads here and here. You’re not alone in feeling like you do, and it’s not an accident that you feel compelled to always be nice and accommodating – it’s what our culture raises girls to be, and there can be consequences for not putting on that friendly mask when you’re in a bar full guys who may be awesome but who may also be Rich Santos.
But just like a Nice Guy(tm), your friendly behavior is a dishonest performance of “niceness” that is not based on authenticity or kindness or actual connection, and I think you would be happier and the world would be a better place if you could learn to cut that shit out.
There is a value and power in being direct and in acting as if the other person will respect your directness that accumulates over time. And there is value and power in being able to receive dislike and unpleasant emotions from other people without internalizing them. It’s naive to think that a woman’s “Hey, no thanks” will always we respected – we have tons of sad, terrible evidence that it won’t always be – but it can help you to set your own boundary and your own expectation for how you need to be treated to act as if it will be respected. It’s not a magical talisman against Schrodinger’s Rapist, but fortunately the vast majority of guys who will approach you are Schrodinger’s Perfectly Fine Guy Who Has Been Trained By the Patriarchy That He Has To Persistently Approach Women and somewhere in that group lurks Schrodinger’s Guys Who Wish They Could Just Drop The Whole Thing And Go Home To A Good Book. And all of those guys, potential predators included, really need to be taught what a clear, direct “no” looks like and that the world will not end if a random woman doesn’t rain constant smiles and approval down on the parched and rocky soil of their hearts.

If you carry in your head an absolute assurance that “no” is a complete sentence and that anything that happens after you say the word “no” is just noise, if you can focus on your own enjoyment and comfort level within any given interaction, and if you can teach yourself to be okay with disappointing someone, I think you’ll be cured. It’s not easy, but it’s an essential part of growing up to realize that not everyone will like you and that you can’t please other people so you might as well please yourself, and that your relationships – at work, in love, with family and friends – will survive some pushback from you.
You dealt with your insecurities about your shyness and awkwardness by learning to be a charming and accommodating person. It’s good to be able to turn on the charm when you want to, but now it’s time to stop being such a goddamn people-pleaser and own your own needs. Some guy in a bar wants your number and the pleasure of your company. You want to be alone with your drink and the nice music. Someone in this little scene is bound for disappointment, so why should it be you? If he says “Can I buy you a drink?” and you say “You’re nice to offer, but no thanks,” and he gets upset, those are HIS feelings born of HIS expectations. Let him go drown those in the delicious adult beverages that also exist at the other end of the bar. He’s not being creepy or out of line to ask you if you want a drink in a bar, no one is doing anything wrong here, but your desires still matter and you’re not being a bitch if you politely and directly state them. He is being an asshole if he throws a tantrum or turns up the pressure.

Let’s talk about directness.
- Hinting doesn’t work. It just creates a sea of plausible deniability for clueless or importunate people to swim around in while your rage level rises.
- Apologizing for or over-explaining your feelings doesn’t work. The more time you spend explaining yourself, the more opportunity you give the other person to poke holes in your arguments or give the impression that you are not sure about your decision and are open to further negotiation. You don’t need to make an airtight case for your feelings, and trying just keeps you engaged with the person longer than you want to be. Plus, qualifiying every statement you make is annoying as fuck.
- Being concise and direct commands attention and respect. Power doesn’t need to repeat itself. Borrow some of that for yourself.
So you talk with a guy in a bar for a little while, and he asks for your number, and you don’t want to give it to him.
DIRECT:
“Can I have your number?”
“I’m sorry, I don’t like to give it out. Do you have a card or an email address?”
“Why bother, are you even going to write to me?”
“I don’t know yet.”
I think a cool guy will be aware of the safety concerns (or the annoyance concerns – not everyone wants a Shiny New Constant Texting Buddy!) and give you the info without fanfare. If he keeps pestering you with “Whhyyyyyyyyyy” and pressuring you to give your info or promise you’ll call him, that is great information: It’s a clear message from the universe to stick to your guns. He doesn’t need to know that you’d prefer to date women just now, or that you default to people pleasing in pressure situations, he just needs to know that you don’t want to give out your number. What he does with that information and how he feels about that information is totally on him.
You could start practicing a script like this when you are out, in a very low-stakes way to get more comfortable refusing advances you don’t want, and to collect some contact info so that you can make up your mind later when the pressure is off. “Hello, this is Deceptively Nice, we met at the bar last week. You seemed really cool, and I’m new in town and trying to meet new friends. Would you want to have lunch sometime?”
I think men owe it to themselves to hear the “no” for what it is and back off completely when they hear it. But I think women owe men (and ourselves, and each other) something here, too: Learn to make your “yes” enthusiastic, your “no” non-negotiable, and to be okay saying “maybe” when you haven’t made up your mind.
If you say no, then maybe, then no, then yes, you teach men that “no” isn’t real and that it doesn’t count and that, by gum, they’ve got to be persistent in getting a woman’s attention because you can’t trust her “no.” There are a lot of historical and cultural slut-shamey reasons for this little dance that we do, so I’m not saying that it’s easy to knock it off or that you are a bad person if you’ve ever danced this dance (I’ve danced this dance) or that women are responsible for men’s behavior or that you can’t change your mind (!), but there’s no need to be one of those elegant females who seek to increase the love of her suitors by suspense. When it needs shutting down, shut it down and then walk away.
Also, heterosexual women need to learn how to ask men out when they are interested, instead of waiting to be asked. Let’s kill the notion that men ask and women make themselves pretty so that someone will ask them. “You seem really cool. Could I have your email address? Would you like to have lunch sometime?” Is that entirely without risk? Nope. Do it anyway.
And if you don’t know the answer? You don’t owe it to anyone to have your mind made up at all times so that you can crisply deliver your judgments. Captain Awkward is all about the maybes. Here’s what “maybe” looks like:
“Can I get your phone number?”
“I don’t like to give it out. Do you have a card or an email address?”
“Sure, but are you even going to call me?”
“I’m not sure yet. You seem really cool, and I’m new here and want to make friends. Can we hang out sometime without it being a date?”
Or: “I’m not sure yet. Can I have your email address now and decide that later?”
Or: “I’m not sure yet, and I’d like some time to make up my mind.”
Lots of ways to say maybe. For now, work on “no.”
Finally, this isn’t just about dating or negotiating public spaces. This is about work. This is about that expensive out-of-state wedding that you can’t really afford to go to. You will gain so much personal power if you learn to say a clear and direct “no” when you need to and then move on without constant self-doubt and apology. The good news is that you can absolutely learn to be direct in expressing it and to live with others’ fleeting disappointments. I’m not just the President of Recovering People-Pleasers Anonymous, I’m also a Member.
Really great posts. Any general suggestions for dealing with the guilt that often comes with saying “no”? Especially since those who guilt trip or ignore “no”s are the people that we often need to get away from the most.
Perhaps the ability to recognize a guilt trip for what it is early on? (Easier said than done, I know all too well, and it’s hard to realize what something is in the moment.) But once you do recognize the guilt-trippers and the ignorers for what they are: people who do not respect your boundaries.
Once that is keyed in on, perhaps say a mantra: “They do not respect my boundaries, therefore, they are not deserving of any guilt I may feel.” Repeat ad nauseam until it starts to ring more truly?
Sounds like good advice. I was mostly asking for a friend who I think has some form of the “Must be nice to everyone in case they’re secretly homeless Jesus” mentality that CaptainAwkward described in a previous post.
Maybe some scripts for getting out the conversation before the can-I-have-your-number part would be helpful too? I know I would love to read them!
You can’t really control whether someone will ask for your number (he thinks he’s paying you the ultimate compliment), but I often go with “well, it’s been good talking to you” and then physically turn away/move away. Or “nice talking with you, I’m going to head back to my friends/book/go to the restroom/put a quarter in the jukebox.” And then follow through – leave, use body language to physically turn away and indicate that the conversation is done. I stay polite until the other person is not polite.
My policy is always that if I’ve talked to someone long enough and am not particularly interested, I’ll end the conversation (end! not “get out of”! nobody can be trapped in a conversation) immediately. Physically leaving is always a good way to do this. Or turn your attention back to your friends. I like to say something like “good meeting you” as well, because I like to try and let people know I don’t think they’re jerks, I’m just not interested in them “that way”.
Aww. This problem. It’s such a widespread problem.
This is the main thing I have to say,
I am actually a really awkward and insecure person, but I’ve kind of compensated for it by becoming really charming and accommodating
Girl, this is all of us. Everyone is awkward as fuck in their own head. Even the guys to whom you’ve been giving fake numbers. Even Hillary Clinton. Even the President… ok, maybe not the President. But anyway, everyone feels the same way as you. Don’t feel like you have to be super-smooth just to hide the burgeoning Awkward within! It’s all right.
Also, please listen to what Captain Awkward is saying about men and dating in general. These guys are not representatives of The Patriarchy coming up to pressure you. They’re other human beings in search of human contact. You have absolutely no obligations other than to be clear and direct with them. Even if you’re theoretically open to dating, even if a guy might be nice or whatever, you CAN just say no. There isn’t gonna be a deposition later on why you said it, and then if your reasons aren’t airtight enough you have to go out with him.
In any case, please realise that what you are doing is already saying no, just in a particularly subtle and actually rather cruel way. A fake number is a delayed-action no, but it’s a really brutal one. Next time you feel tempted to do this, imagine that you’re throwing your drink in his face, or saying, “No, and fuck you”. That’s the kind of rejection you’re delivering. Wouldn’t it be much more civil to be straightforward and respectable?
Of course, I’m speaking from the inside of this situation as well – I used to do this kind of thing all the time. Or I’d give out my phone number and just never pick up. It was mean. I always felt bad after doing it.
You’ll feel so much better if you figure out how to handle these situations honestly!
I have not often been bothered by men interested in me; I tend to always be the pursuer. But I do attract conversation from unwanted partners at every turn. Something about my face, I guess. I empathize with them too long, give too much kindness, but find that ultimately, I can think of the exchange as a nice, interesting shared moment if I can end it on my terms and not ages later on theirs. I get some good stories out of random strangers!
That said, if someone actually asks me out, I get completely flummoxed. I know how hard it is to get brave enough, I know how painful it is to be rejected, and I don’t want to be mean. I have a shameful way to try and safe face for both of us which does admittedly work better online than in person, which is, “oh that is so sweet of you to ask. However, I have just started seeing someone, and I would feel weird accepting your date/whatever while I am seeing someone else.”
Yes, maybe it’s a lie, but it’s not an out and out rejection of them (in their eyes) so it helps them save a little face. And if they are a wanker and say, “then where is he now?” you can go all cool adult assertive and say “I like to do stuff BY MYSELF as well.” Meaning also “I came here to be by myself.” Not overt but, you know, gives them a toehold for dignity while ending the negotiation on your terms.
Is that assholeish of me? I hope not. But it does work.
It is sad that men will accept the “This lady is already owned by another man” excuse more readily than “This lady has decided for herself that she doesn’t want to hang out,” but if that’s what lets everyone save face and go back to having fun I can’t fault it.
I have sort of a related question. What if the guy asks for your phone number in front of an audience?
I used to have a hard time saying no to a request for a phone number, but gradually learned to stand my ground. But a few years ago, I was completely caught off guard by a guy who asked me in front of dozens of people in extremely close quarters. I could tell that at least some of the people closest to us overheard him, and I couldn’t bear to reject him in that situation. Instead, I gave him my number and then responded to his phone calls later, saying I wasn’t interested after all.
My response was also influenced by what was obviously extreme desperation on his part, I suspect due to his repeated failures with women; he was quite possibly the most socially awkward man I’ve ever met.
Yikes, that makes my skin crawl. I hate public “surprise” marriage proposals for the same reason. “Will you marry me? Surprise! NO PRESSURE OR ANYTHING, EVEN THOUGH EVERYONE WE KNOW IS WATCHING!”
I’d probably go for “Wow. Sounds like something we should talk about later!” and if he didn’t move on from the topic, let him fall on his face. “No. Really. Let’s discuss that later.”
“Will you marry me? Surprise! NO PRESSURE OR ANYTHING, EVEN THOUGH EVERYONE WE KNOW IS WATCHING!”
I wish we would separate out the asking-a-serious-life-changing-question part from the giving-you-a-symbol-of-our-lifelong-commitment part. Then we can have all the joy of the cheesy “ring close-up on the huge-o-tron” moments without the pressure on *either* party.
Ugh! Soooo true, with the whole ‘being raised and acculturated to be nice and accomodating and then discovering that it leaves you ill-equipped to deal with creepers.”
Becoming an assertive person if you’re not naturally one can be very hard, but like everything else, you get better with practice! You may want to take a self-defense class, because a lot of those will have assertiveness training where you get to role-play with other students about how to politely but firmly assert yourself in situations like this, or seeing a therapist who can help you develop strategies for these scenarios. It may seem silly, but you wouldn’t hop on a bike and go on the Tour de France without training – and it’s a lot easier to respond when you feel flustered if you’ve already practiced and have a few stock phrases to whip out. Practice in a mirror until you get rid of that nervous-smile and have perfected the Single Arched Eyebrow of Doom and the “how…niiiiiice” conversation killer.
Also, please, please stop giving these guys fake numbers. Seriously.
Okay, as a guy, please do not give guys false numbers. If you don’t want to go out with a guy, you’re doing him a FAVOR by just saying no outright (politely but clearly), because by making the rejection direct (and not rude) you make it relatively easy to take. Most guys who just come up to you at random are used to that kind of rejection, because in order to get someone’s number legitimately that way you need to take a lot of rejections.
If I may make a silly analogy, would you rather not have any money, or would you rather find a $20 on the ground and discover it’s counterfeit when you try to pay for something?
I agree with this!
Though, as a lady, I must ask you: Stop asking for numbers from people you don’t feel a connection with and probably won’t call. Let’s clean up dating karma FOREVER!