Hello there! Michigan was awesome. I’m just getting back to email now, so I apologize to anyone who spent all weekend in the moderation queue wondering “What did I say?”
So, I swear I’m not turning this into a PUA site for people who want to date feminists, but this question came in right on the heels of the whole “How do I seduce women” thing so I thought I’d knock it out while we’re on the subject.
Dear Captain Awkward,
Also, I’m kind of shy and awkward, so I’m bad at flirting. It’s not that I’m creepy or anything, at least I don’t think. I don’t nakedly proposition, I don’t corner, I’m not lewd or graphic or anything. If anything, I’m more likely to have the opposite problem of someone doubting whether I’m asking them out on a date, as opposed to just hanging out as friends. When I was in college, I flirted so ineptly with a girl in my dorm that she nicknamed me Sketchy Greg, and that nickname stuck for the rest of the year, which traumatized me about flirting and hitting on people that I might have to encounter again. Basically, I already have a preexisting phobia about developing a bad reputation, but I’m extra worried about developing a specific kind of bad reputation that will undermine my work.
I don’t want to completely shut out the possibility of meeting someone this way; the fact that we’re both at an event to promote a particular cause suggests more compatibility than you’d find in a bar or online or something. But I also don’t want to put my own social needs above the needs of my organization. Is there a good way to navigate these pitfalls? Am I just being paranoid and insecure for worrying about this in the first place?
Thanks,
Awkward with Women
Dear Artist Formerly Known as “Sketchy Greg:”
Here are links to some stuff I’ve written about dating while feminist that cover the rules of dating:
- Dating While Feminist
- A Shy Guy Caught My Eye (a general guide for asking people out)
- How do I seduce women? (An eye-roll inducing question,but it reiterates the CA Dating Guide for Geeks)
Okay. It’s good that you’re volunteering with feminist organizations, and it’s good that you’re thinking about boundaries in using your work there as a springboard to jump start your dating life. Meeting people through common shared interests is a good way to meet people! And it’s good you’re trying not to be a douche about it. We’ll call that the good news.
The bad news is that your premise is faulty to begin with. I understand about being a nerd and wanting to do research and homework to find out The Correct Way to do things. But asking a woman “How do I interact with women?” is by its very nature unfeminist. There are approximately 3 and a half billion of us on the earth, so the answer to “What do women like?” or “How do I talk to women?” or “Where do I meet women?” is pretty much “I don’t fucking know, we are all different and also we are just people.” To be even more specific, just like men (who are also people), most of us have not fully unpacked how we would like to be approached. We know it when we see it. We know what we don’t like when we see something we don’t like. But there is no system or way that we’ve all agreed on at our LadySummits. As one commenter said recently, women are not the Boss level of a video game and there are no Lady Cheat Codes. There is some good basic stuff (including a reiteration of the above principles) at the Geek Feminism Wiki.
Saying “I’m awkward with women” tells me that you’re holding onto some sexist ideas about what it would mean for a man to be “good with women.” Those ideas are baked into the toxic cultural soup we were all raised in, so it’s not completely your fault, but if you want to be an activist and a feminist it would be good on all counts if you could shed the idea that there is a way to be “good with women” that’s separate from learning how to be more comfortable in your own skin and good with people. If you feel awkward around women, who are people, work on improving your social skills in general. Get better at talking to dudes, and you will also get better at talking to ladies, since both ladies and dudes are people. Do a little reading about stereotype threat, and leave the idea of “Sketchy Greg” behind. You’re out in the grown-up world working on activist causes you believe in, so you’re probably much better at talking to people and being cool than you think you are. Speak truthfully and directly about things that are important to you. Be kind. Ask questions and listen to the answers. Don’t invest any one interaction with too much meaning. Look for reciprocity in your interactions with other people. If you’re doing all the work of trying to impress someone, you’re performing instead of connecting, and it’s going to be weird and uncomfortable. This is basic good manners and will help you in any social situation.
I guess what would make me feel better about your question, Awkward With Women, is if you’d written to say “I work for this advocacy organzation, and I met this really cool woman and we’re always hanging out together late after the meetings and running into each other at fundraisers and stuff, and I want to ask her out but I don’t want to overstep some unwritten work/friendship boundaries, what do I do?” In that case I could help you. I’d say scan the local paper or free weekly for something cool and inexpensive to do that you think she’d like (because you’ve spent time together and have some idea of what she likes and where it matches up with stuff you also like), and then use a mad lib like “Hey, I plan to go to (music festival)(reading)(opening)(lecture)(art exhibit)(play)(try this new restaurant)(beer tasting) on (day/time)(next weekend)(later this month), would you like to join me?”
If she says “Are you asking me on a date?” the answer is “Yeah, is that cool?” Don’t try to deny that it’s a date, because THAT’S how you end up in creepytown where you’re all full of shame and lust but you said it wasn’t a date so now you are a weirdo if you try to stealthily turn it into a secret date – secret from her, that is until you hug her and she feels your pulsating boner against her thigh – after the fact.
She’ll either say yes (in which case firm up plans) or no, in which case say “Ok, just thought I’d ask” and then go back to normal interactions. If it ever gets brought up again she will be the one to bring it up.
This is a good time to actually expand on the concept of reciprocity, ie, the interactions involve a give and take with each person putting forth the same amount of effort. An example of reciprocity is you asking the woman you like to an event, and she says she can’t make it, but she lights up with a huge smile and suggests an alternate event you might go to another time. You have to trust that if someone is interested in you, or open to the idea of dating you, that she will make some effort to show her interest even if your first suggestion is not the right one. It’s easier to achieve reciprocity if you keep it light and don’t get too invested in the outcome. If she doesn’t show interest (huge smile, agreeing, making an alternate suggestion, saying “I’m busy this week, but can you ask me again later in the month?”, etc.), let it go. She’s either not interested, or too high-maintenance and hung up on old ideas about how men are supposed to “chase” women for you to want to get with her.
If the person you are interested in is also a geek it might take a few false starts to get there. For example, I am also terrible at flirting or noticing when someone is flirting with me, so someone I like might ask me out and it might take three days for it to dawn on me what just happened. During those three days you might feel really bummed out and embarrassed and wonder why I hate you, but on the 4th day if I was feeling it I’d probably call you and say “The other day when you asked me out? That was nice, and I’m sorry I behaved like such a dork. Can we try that again?”
None of this advice is really germane unless you have a specific person you’d like to go on a date with. I feel like you’re writing to me for some kind of blanket permission to mack on the women you work with and some kind of system to guarantee that it won’t go awry when they all find out about each other. That I can’t help you with. Of course you can and should ask out people that you want to go on dates with and have a ton in common with and who are part of your social circle. If there is someone you find yourself thinking about after you leave a meeting and hoping that you’ll run into at the next meeting, go for it! Slowly! And one at a time! You’re not stupid paranoid to worry about your reputation because people talk to each other, and will quickly figure it out if you ask out one woman after another after another. It gets back to the whole “women aren’t interchangeable” thing we started with.
CaptainAwkward.com 
“Single-issue attraction” seems to be the problem here. There’s nothing wrong with being attracted to a certain quality; there’s nothing wrong with “feminist” being one of those qualities (it’s a big one of mine; it even says so on my online dating profile). But if you’re in a room full of feminist women and you think, “I want to date ANY ONE of these women” you have a problem.
Women aren’t gumballs. You put a quarter in the gumball machine and one comes out; doesn’t matter which. Thinking, “Boy I really hope it’s a *green* gumball!” doesn’t bring you any closer to humanizing the individual gumballs.
I’ll admit that I’ve attended a Planned Parenthood event and looked around at all the smart, hot, politically active women and thought “I should tell my single male friends to come volunteer here – 1) because family planning is a human issue and we need more men to be involved and 2) they’d be knee-deep in hot smart ladies who know about teh sex” but once you’re in the door it’s just as much of a crapshoot as anywhere. “Is there someone specific I find attractive who is also specifically drawn to me and when we interact with each other is it nice?”
I wish my single male friends would volunteer with Planned Parenthood, and it not be like Hugh Grant at the single parents group. Because yes, so many smart, hot, politically active women there, of the kind my guy friends would like and don’t seem to meet. The only straight men I’ve seen at volunteer events are dragged there by girlfriends. Boys, Planned Parenthood does great work, volunteering with them is fun, and you will meet awesome people of the female persuasion. Don’t look at it as a pick up joint, look at it as a way to get to know awesome people. And give out so many free condoms it becomes a joke among your parents and their friends.
If AwW has that much anxiety about this, maybe he should look elsewhere for his dates. If he wants to meet someone with a compatible worldview, he can add “I volunteer for [femgroup] in my spare time” to his online profile.
Learning to relate romancewise is hard enough without raising the stakes even higher.
Online dating was made for the shy and awkward. Good call. Though if he’s meeting a specific woman at these events and feeling like he wants to ask her out, “I really enjoyed talking to you at the thing, would you like to grab a drink next week?” is not a violation of the social contract.
I feel like I should clarify I few things that I left out of the original letter.
I couldn’t think of a good sign off. The “awkward with women” thing was more of a silly pun than anything, kind of using the common expression to pun on the fact that I was awkward and surrounded by women. I’m not great at sending or interpreting dating-related signals, but I don’t consider myself particularly awkward with women per se.
Here’s a bit more context. This was in fact borne out of a specific situation. A week or so ago, I was hanging out at a Planned Parenthood event with a couple of women and I realized that I had asked out both of them and they both had said no, and I wondered if they’d talked about it. That was in the back of my mind during that interaction and later when I went to another fundraiser and met a specific person that I hit it off with. I probably would have asked her out on the spot, but the concerns I raised in my letter were on my mind and so I didn’t.
I don’t ask women from this circle out very often; the three I mention were spread over two years. My concern, I guess, is that every time I ask someone out, the number gets larger and the stakes get higher for next time. I wouldn’t say my intention was to ask for permission. In fact, in a lot of ways the most helpful reply would have been “Don’t hit on women you meet at Planned Parenthood fundraisers ever”. So to refine my question more, what sort of behavior should I avoid to prevent earning, deservedly or not, a bad reputation?
If you’ve been cool about the rejection(s) and it’s not like we are talking about a very specific group of 30 women who work together all the time and you ask them out one after another, until you asked a third of them, it’s fine. But your last sentence sounds a bit … alarming(?) to me. Either you were cool about the rejections and can work well with all of them, so no one has to feel uncomfortable. Or you behave somehow creepily. But I can’t imagine any behavior, besides “not being creepy”, that could avoid problems. Either you are sketchy Greg or you aren’t.
But if your anxiety around this is so severe, I’d recommend to date outside this circle, too.
Hi Greg, There is a factor which I think you’re leaving out of your considerations: assuming that you don’t come across as a creepy kind of guy (and assuming you were open about asking them out and then taking no for an answer, there’s no reason you should have come across as Creepy Kind of Guy) then the most obvious answer is, the first two women just didn’t fancy you. It happens. It doesn’t mean you’re unattractive and it doesn’t mean you lack the mythical Feminist Mojo. It just means you weren’t the first woman’s cup of tea and you weren’t the second woman’s chocolate biscuit. No one is universally attractive to everyone.
It’s entirely possible that woman one and woman two have talked about you. So? Did you do anything that would make either of them talk about you negatively? That is – did you react badly when they said no? If you took their saying “no” with grace, and have been friendly and not pushy with them ever since, that’s actually positive – it means you’re gaining a solid reputation as not Schrodinger’s Rapist. (It’s kinda sad that has to be mentioned as a positive factor, since it ought to be the default standard for behaviour. But so it goes.)
If you are building a solid reputation in this social circle as a guy who is open about his intentions and takes rejection politely, that makes it more likely that a woman from that social circle will, if asked out by you, decide to say yes, if she finds you attractive, because she knows in advance from friends that you’re one of the good guys.
If you feel now with the benefit of Captain Awkward’s advice that you handled the first two approaches wrong – you weren’t clear about your intentions, you didn’t take a “no” gracefully, well, maybe you do need to move on to a different social circle and start building a better reputation by your actions there.
I speak from experience as a lesbian in a relatively limited social circle where the odds are high that the person you ask out will already have been on dates with people you’ve asked out before – where you can know quite a bit about a person from their social reputation, from friends talking to and about you, before you ever go on a date. Sometimes that’s bad. Sometimes that’s good. Live with it.
Maybe they have talked about you! You can’t control that. If you’re still able to hang out and work with them and it’s not weird, then you didn’t develop a “reputation” except as a guy who is cool at handling rejection and fine to work with and be around. You can do everything right and the other person can just be not that into you.
I’m sorry if I misinterpreted your awkwardness level – I only have what you tell me to go on, so when you tell us the story of “Sketchy Greg” and sign yourself Awkward with Women, I drew certain conclusions.
I’m normally for asking people out sooner rather than later, because if you start planning your asking out like the D-Day Invasion you invest way, way, way too much effort and thought in it to be actually cool with rejection. But with this third, specific, mystery woman, I’m tempted to tell you to ride it out for a few weeks or months. If you really hit it off, she’ll be thinking about you, as well. When you are at the same events she will seek you out and you will have more conversations, and after a few times of seeing each other you’ll have more of a basis for saying “I always love running into you at these things, would you ever want to grab dinner?” If you really hit it off, maybe she’ll ask you.
In other words since asking out this lady bears some risk for you professionally and socially, hold off a little while until you have a stronger basis for thinking that there is some good chemistry between you. Give her some room to seek you out.
She may talk to the Women Who Did Not Go Out With You about you. You can’t control that at all, and the only way you can screw that up is by trying to control it. If someone generally cool-but-not-for-me asked me out and I said no, and then 2 years later they asked out someone else in the same social circle, my thoughts would be something like “More power to you, I hope that works out!” And if she is talking to the Women Who Did Not Go Out With You specifically about you, it’s a good sign that she’s thinking about you in a dating way, aka “What’s the deal with that Greg guy? Is he single? He seems really neat.”
Exactly.
Maybe TMI–I did the online dating thing for awhile, and met a lot of guys who liked but not in that way. I enjoyed spending time with them, but knew it wasn’t there for dating potential, and wasn’t going to suggest being friends because no one is on those sites to find buddies and pals. BUT–if a mutual friend asked me about any of these guys, I would tell her that they are very personable and interesting and [insert specific characteristic of particular man here]. Just because someone’s not a good fit for me doesn’t mean that he should be condemned to be dateless forever. . . and if I like them in general, I’d like to see them with friends of mine because I like seeing nice, cool people get together and be happy.
/Monday morning Pollyanna
“I’m normally for asking people out sooner rather than later, because if you start planning your asking out like the D-Day Invasion you invest way, way, way too much effort and thought in it to be actually cool with rejection.”
This “effort problem” plagued me greatly when I was young – I thought too little of myself and thus believed I needed to come up with some fantastic way of asking women out. It made it a high-pressure situation for both of us and absolutely did not work.
Eventually I realized if I met someone and she seemed to like me, I could just ask her out and if she said no, it was OK. Sometimes (usually not) a few months later she’d ask me out.
Remember always: there are no “leagues.” Someone who has good chemistry with you probably finds you quite attractive, regardless of your “cultural attractiveness rating” with the general population. Thus if you are thinking of asking a woman out who seems much hotter than you – that’s a good thing. Hot people are fun to date, even if it doesn’t go anywhere. Ask her out casually, no pressure. If she’s used to being asked out, that’s how she likes it – casual. If she’s not used to being asked out, it’ll make it less awkward for her as she tries to figure out how to react.
I think you’re completely correct, ApeMan.
I would advise asking out as many people as possible, not just people you would like to have sex with and not just to things that are meaningful, but just to desensitize yourself from the act.
Like: I’m going to get coffee? Would you like to ride along, work-mate? Would you like me to get anything for you?
I’m going to the grocery store, neighbor, would you like to come with me?
Is anyone interested in seeing this movie I’m going to?
Etc.
If this is an action you only take when you really, really like someone and can’t keep yourself from daydreaming about what it would be like to have sex with them and grow old happily, then of course it’s going to be super fraught.
Also, having company makes stupid chores more fun anyway.
Yes! Learn to ask people to hang out when it is not fraught….with boners.
Cap’n, I propose that our first album be titled “Fraught with Boners.” Can I get a second?
I also agree. Some of my most fun dates were of the “hey, this conversation is fun! Let’s continue it! Coffee?” variety.
Hi, Guy!
Just FYI, I don’t really talk about the men whom I’ve turned down. If it were to ever come up, it would be more like, “Um, yeah, a year ago but we didn’t go out. He’s cool though.” Shrug and change the subject. Contrary to my online presence, I’m not typically a bitch from hell, unless someone makes me feel very unsafe. In which case, I will get medieval on their ass. But I digress. Someone asking me out and accepting a no with grace and generally backing off is not someone that would inspire me to go from zero to bitch in under sixty.
They may be talking about you sometimes but if you know each other and and are generally friendly with each other and you accepted the no’s with good grace it could just be “I really like [LW]’s jacket, he’s a snappy dresser,” or “I think [LW] did [activity] before so maybe you should ask him about it if you’re thinking about doing it.”
And just FYI, I only learned how to flirt a couple of years ago, and I’m 42. And I don’t really tend to flirt unless I’m already involved with the guy. (So you’re not alone in this.)
Thanks for all the advice; I wrote as much for the crowdsourcing in the comments as for the Captain herself.
I take rejection fine. My reaction is usually to try to pretend I never brought anything up to begin with and try to go back to normal. The Sketchy Greg incident kind of did a number on me. I’d never been the subject of gossip before, I don’t know what I did to earn a reputation or whether I deserved it, and the lesson I learned from that was “flirt awkwardly and you will pay.”
I basically ended up converging on this advice myself. Basically, just have a higher level of confidence before asking out someone within the circle.
Hey friend. I think you’ve had plenty of good advice and encouragement, and it sounds like your head’s screwed on okay. I just want you to know that I have my own “Sketchy Greg” that resonates in my head to this day.
Mine? “You smell gross.”
I do not smell gross, but the idea that I might… it’s in there pretty solid.
I think the worst thing you could do is try to be Anti-Sketchy, just as the worst thing I could do would be to bathe in cologne. Just as the tonic to my situation is basic hygiene and on occasion asking trusted friends “Hey, srs now, do I smell bad?” you’ve already enacted the tonic to Sketchy Greg: Basic Human Interaction + check-in with trusted people wrt potential sketchitude. Go you!
“LadySummit.” Love it. Also huge points for user name “Sheelzebub.”
I’m 41 and a hopeless moron when it comes to flirting. Sometimes direct is appreciated. But ALWAYS coolness and low keyness is appreciated.
As a woman who attempts to date while feminist, I have to say — I’d love to be asked out by more openly feminist guys.
HOWEVER, I will be able to tell if said guy is just in it for chicks. But a genuinely involved guy who can talk smack about the patriarchy, and is asking me out because he’s into *me* as a person? Well yeah, that’s cool. Even if I’m not interested, it’s still cool.
Awesome! Also, you should ask out more openly feminist guys!
I do my damnedest; definitely not against asking out people! And I’ve married one! 🙂
(Also! Even if feminist guy and I don’t date, I’d be very happy to have him as a friend!)
Back when I started dating, knowing that I didn’t want to date non-feminist women, I was worried that people would think I was “in it for the chicks,” as it were. I never ended up having that problem, because like maggie said, feminist women can generally tell. And guys who think that they can fake feminism are way more obvious than they think they are. At best they come off like, “OH MAN THAT ANDREA DWORKIN HUH?! PATRIARCHY AND SHIT RIGHT?!”
Props for including stereotype threat as a factor here, Captain!
“Artist Formerly Known As Sketchy Greg” I think you sound like you have a good head on your shoulders and are starting to get your shit figured out in a big way, so congrats. I echo everyone who said that if I talk about a guy who turned me down or whatever, it’s usually in a positive way unless he was giving off bad, bad, like truly terrible, vibes. In the situation you describe above I’d probably be like, “oh yeah, we’ve chatted before, I’m pretty sure he is single and looking *wink wink*” so you know, women talk about men in plenty of ways that don’t include the phrase, “oh you mean that sketchy dude? yeah super sketchy, I tell ya”