Talking to Women, Gchat Crises, and Pre-Adolescent Encounters

by A Lady

What is the “right”/”best”/”most appropriate” way for a strange man (me) to approach a strange woman (not that we are odd, but that we are strangers to each other)? I am painfully shy, and even though I know I should just say “hi,” I can’t bring myself to do it. I have the yips. I get nervous, and then I do nothing, and then I regret my wallflower-ness the rest of the day. Even when a strange woman smiles nicely (politely?) at me (is she sending a sign, like, “hey, if you won’t do it willingly, come talk to me you silly fool”?), I often can’t return the favor. I get scared. I start thinking, “If I tell her I think she’s pretty and ask her for a drink, will that seem creepy? Does that make me strange?” I am scared of rejection (I would probably die of embarrassment if I were rejected in public), though people tell me I have nothing to worry about.

I am in my mid-20s, I’ve got two college degrees, I speak two languages, I never go out without a lighter and a handkerchief, I hold doors and stand when women leave and arrive at tables, I’m well read and well travelled, and maybe even a little interesting if I could bring myself to have a conversation with someone I didn’t know. Women friends even tell me I’m not so bad looking (I know they’re just being polite though; they’re friends, they’re obliged to say those things to a person with no confidence). OK, yeah, I’ve got confidence issues. But how should I go about saying “hello” and “I think you’re really pretty” and “I’d very much like to take you out for drink” to a woman I don’t know? Do women even like this happening? Won’t you just reach for the pepper spray or a blunt object if a man just ambled up to you in, like, a book store or something and said “I hope you don’t mind my saying, but I think you’re really pretty”? Maybe I’m just looking for validation from women that I just have to get some courage and say hi and things’ll be fine.

But seriously, what do I do? I’d like to talk to women, but a) I am actually scared to do so/of women, and b) I don’t really know what’s appropriate to say and I don’t want to seem a creeper. I think you’ll need to give me more advice than “just say hello,” since that’s failed me (or I’ve failed it) up to this point. Feel free to make any comparisons to Charlie Brown and the Little Red-Haired Girl, because that’s basically my life.

OK. I am throwing out like 90% of your question, including your list of, like, qualifications to talk to ladies and your catalogue of insecurities. I have no way of pronouncing whether you are going to be attractive to any given human lady at any given time; I live in a computer. (Confidential to commenters! I know you, like A Lady, probably have varying opinions on some of the particular characteristics and behaviors listed, but we can all agree — because I am telling us to — that they are within the wide range of human behaviors or qualities a lady might reasonably find attractive. I am feeling protective of this dude for some weird reason, and as long as he doesn’t smell like pee, or punch people immediately, or behave in other genuinely insane antisocial ways, we are going to let him be a bit of a sadsack and do his handkerchief thing or whatever.)

Stripping away your attempts to justify your existence, I am left with “A Lady, I want to talk to ladies I don’t know in public, but I am not sure that is a normal thing to do, and if so how do you do it?” Assuming we’re not talking about bars here — and I DO assume that we are not, because you mentioned bookstores, I will say straight up, you know what, people don’t do it that much. It doesn’t mean it’s not a potentially great way to meet people precisely because it’s not that common, but most people meet potential dates at bars, parties, the internet, through friends, etc. and not in neutral public spaces. So your anxiety isn’t weird in that respect — you want to try to do something that not that many people do. I am totally pumped for this, and have a two-step process that you are going to follow before writing A Lady back at:

A Lady c/o Edith Zimmerman
The Hairpin
The Internet, NY
America

and we will discuss how it went.

Step (1): This is the best life-advice I can give you or anyone else. You Can’t Read Minds Even If You Try Very Hard, hereafter YCRM (pronounced why-cram). You say if you got rejected in public, you’d die. Because some girl had other shit going on in her life that meant she wasn’t into you at least in that time/place, you’d die, even metaphorically? Seriously? Calm down. You cannot speculate on what any given girl’s decision-making process might be or how, exactly, it intersects with your behavior. So, first, we are agreeing that you can’t read minds, and when you get rejected, which you inevitably will, your thought process will be something like “too bad that girl wasn’t into it! Bummer! I would like a croissant now.” No, “I wonder what she…” or “did she think I…” or “Because she X, I must suck at Y.” If you catch yourself thinking that way or even WONDERING what went through her head, remember, YCRM. You will never know, also, we are all born alone and die alone. Finally, if a girl rejects you particularly meanly, like actually says something nasty or derogatory, you have my permission to decide that shit is actively her problem and be like, “wow, what a bitch” (in your head) before you get your croissant, then no more thinking about it, whoops, you tried to hit on a total bitch (it’s cool, total bitches, I love you guys). And … scene.

(2) We are going to come up with a list of 2 (two) normal human behaviors that you can reliably turn to as a way to initiate conversation with girls in non-bar public places. As a normal human, I personally certify that these are OK ways to act, and that if people respond poorly to them it’s not because you did something crazy fucked up and abusive and antisocial. OK?

(a) Behavior 1: “You’re pretty, want to get a drink” is not going to get you too far unless someone’s already attracted to you — that is, I don’t think it will make them become attracted to you. Look, the world is full of pretty girls. There’s a reason this one in particular is making you all fluttery. Figure out what that is, and after necessary editing, tell it to her. Is she the one who smiled at you? Can you tell her she has a sweet smile? Does she have a particularly interesting pensive expression while she reads? Great style? Be specific, but keep it to the head/face/general appearance. I mean, I trust you not to be like “your rack is astounding,” but even “you have a charming way of drumming your fingers” gives me a creeper vibe. Any response? Keep the conversation going for five minutes. Sorry. You have to do this part. Use the context. Bookstore? Books. Park? Favorite spots in said park. Whatever. Ask about her, don’t talk about yourself unless she asks. Does she live/work in the area? (If she answers, don’t be like “where, exactly, including the buzzer number?”) Is she from here originally? Whatever. Small talk. It sucks, just do it. After five minutes, you can say “hey, I have to run to meet someone/back to work/whatever, but I’d like to take you out sometime.” Note: “I’d like to take you out,” not “I’d like to buy you a drink.” If this works out, you will spring for a fucking banh mi like the gentleman you are before you go to a bar. Or at least go to a bar with food.

(b) Behavior 2: You say you have female friends. Make them work for you. Something like “Hi … my friend didn’t want to bother you (NOT “is shy”) but he was saying how pretty/stylish/whatever you seemed, and he’s such an awesome guy I decided I had to at least TRY to make an introduction… “ This is such an easy yet effective move. Get on it. Then, same thing, five minutes chatting, maybe work in a compliment to her head/face area as discussed above, then “I have to run but I’d like to” (all together now) “TAKE YOU OUT SOMETIME.”

Now. There are dozens upon dozens of more advanced/complicated moves, but the genuine compliment and the wingwoman (WOMAN. Woman. Only woman.) are two excellent starter techniques — one really requires you to dive in, and you can refine from there; the other is very, very safe and carries no risk of being rejected to your actual face. I want you to try them both two times in the next week. Yes, it’s kind of a lot. Tough. Get out there. Tell me how it goes, I’m genuinely curious.

Also if you ARE talking about meeting people in bars, whatever, just drink more.

So I have a friend from graduate school who I like very much. This friend is one of the most busy, motivated people I’ve ever known, and coordinating time to actually hang out with her can be difficult, especially since she started an extremely demanding new job, so we haven’t seen each other in a while. The sad thing for me is that I also haven’t seen her on Gchat in several months, which is the way that I tend to try to stay in touch with friends who are far away or too busy to hang out. And at first I thought that because of said demanding job she had just stopped coming on Gchat, or just gone perpetually invisible. But then a couple of times mutual friends dropped references to her status messages, and I just confirmed that she’s been online, I just haven’t been able to see her.

So I see three possible explanations for this: 1) I offended her horribly in some way that I am completely unaware of and she somehow transformed from the straightforward normal person she usually is into some sort of passive-aggressive troll; 2) she cleared out her friends list except of the most important, special-est people and I didn’t make the cut; or 3) there was some sort of innocent mistake (maybe she was clearing out all but the important, special-est people and she accidentally hit my name while trying to get rid of some scrubby former hookup?). While the low-self-esteem demons in me are screaming for the first two explanations, my rational side (which has about 30% control…) is arguing that 3 is the most likely. BUT, even if that’s the case, how do I broach this with her without a) sounding as whiny/oversensitive/paranoid/neurotic as I do in this email; and b) creating a really awkward situation if the actual explanation is 1 or 2?

I really miss my friend and I’d like to be able to chat with her from time to time.

Oh my god this is so YCRM it’s literally killing me, I can’t even answer, because I’m actually dead as of right … now.

OK, wait, I came back as a ghost. A Ghost Lady says: Even with my extraterrestrial powers I have no idea why you are off your friend’s Gchat list. I can imagine dozens of reasons without even trying, some of which have to do with her being annoyed with you and some of which don’t. I don’t know, you don’t know, no one knows! If only there were a way, some kind of magic spell? so that when we were missing a piece of information, we could somehow try to gain it?

Obvi what I am saying is you have to either let this shit go or Ask A Specific Lady. Even if the answer is awkward, feeling awkward for 10 minutes is a better use of your time than attempting amateur clairvoyance. So what you say is: “Hey, Heather, I mostly use Gchat to keep in touch with people and hadn’t seen you online in forever. Is everything OK?” If she’s like, “What, I’m on all the time, oh shit I accidentally blocked you,” you have your answer. If she is like, “Oh, I’m just not on a lot,” we know she is for some reason trying to talk less with you. Why? YCRM and also fuck that bitch you’ve got some REAL friends to be Gchatting with anyway. If she’s like, “It really pissed me off when you slept with my underage brother and guess I was being kind of passive-aggressive about it,” well, talk that shit through on its own terms.

I am so over being a lady! I am so sick of spending hours doing my hair and makeup, spending my hard-earned cash on clothing, bikini trimming, dieting, sunless tanning, moisturizing, fighting pimples, teeth whitening, wearing heels, wearing bras, wearing tight jeans (and then dealing with the subsequent yeast infection), etc. etc. etc.!!!! I am so jealous of my husband. He takes a shower, brushes his teeth, throws on a uniform (suit and tie) and calls it a morning. I’m getting so tired and angry and resentful. Sure, I could stop doing all of those things, but you know how society is … let’s be real.

You recently broke the news to another ‘Ask-a-Lady’ reader that the mess after condom-less sex is part of womanhood. ARGH! I want to be a man. I want to just stick it in my lover, orgasm, and fall asleep. My husband gets frustrated because I’m not willing to have sex late at night or whatever. But, god, it’s so hard for a girl. We can’t just get hard. We have to foreplay, fantasize, get the motor running … then, afterward, we have to clean up to avoid that sticky “old sperms” feeling. It’s an impossible situation!

How in the world do I deal with this resentment and anger?? I am so tired of all of the demands put on me just because I have a vagina. Help!

BUBELEH. Big hug. First of all, congrats on even making it to angry, most of us just hate ourselves until we’re 60. You basically warpzoned straight to Advanced Woman.

Now, in general, I am pretty sympathetic to dudes and their dudely problems, because I think they, too, get fucked pretty raw by … ugh, I hate “the patriarchy” and equivalently fussy terms (do not EVEN come at me with your “kyriarchy”) … let’s call it the jerkcircus from now on, OK, I had everyone in the room vote, it’s jerkcircus now. Furthermore, I don’t know if your resentments and mine align perfectly; you’d have to wake up pretty early in the morning to convince me that being the gender that gets to paint itself is a net loss, though granted you probably do wake up pretty early in the morning, because you know, you are putting on makeup.

But I do know, like you do, that some. Shit. Just. Sucks. For. Women. Plenty of the sucky stuff is strictly a result of the jerkcircus, and some of is having these bodies that like, might make babies? And we’ve all been at the jerkcircus so long it’s impossible to even tell which is which and after a while who cares anyway and we’re just exhausted and lonely and want to lie down and wail toddler-style until mommy makes it go the fuck away. Except guess the fuck what, you ARE mommy now, SUCKA.

My main point is: Yes. But you didn’t ask me: “This stuff, yes or no.” You asked me what to do with that anger. Hm. The grown-up answer would probably be like, oh, channel it into activism! But whatever, that’s it’s own ring in the jerkcircus, and unless you have an independent inclination in that direction, I’m not gonna sell it because I wouldn’t buy it. What’s brought me a lot of succor in these most stupid of times are my friendships with other women? I don’t think in the youthiest part of my youth I realized these were something to cultivate and a resource I could use as opposed to just being fun and nice and easeful. But it’s my hunch that you’re never gonna be able to navigate — manipulate, even, can we hope? — the jerkcircus if you are not fiercely caring for and letting yourself be cared for by other exhausted, angry, lovely women, because that’s the only context where that exhaustion and anger are going to be a bonding, rather than a distancing force? And I don’t get the sense you want it to be a distancing force, ultimately? Like, you want to be with your husband, I think, because you aren’t like, I don’t want to be with my husband, and you don’t want to go totally rogue, because you’re not looking to stop wearing your super sexy yeast infection jeans (I wouldn’t either, it’s cool, I just happen to prefer too-short skirts). So basically, a personal squadron of Amazons is a big help, at least for me? But god, it’s such a fucking bummer sometimes. Sorry.

Oh also, watch Meek’s Cutoff. It’s all about this and other shit but I think mostly this and it will blow your mind and if you don’t see how or it doesn’t blow your mind, you are wrong. No but seriously everyone go see it and I don’t even want you to complain about then ending because the ending is correct. This Ask A Lady has totally not been written by Michelle Williams, at all, nope.

I’m a man in my late twenties and I’ve been seeing an amazing woman for a while now. Recently, we had “the talk,” disclosing our sexual histories to one another.

I trust that she came clean, as did I … mostly. I neglected to mention that I had some pre-adolescent same-sex experiences. These experiences never amounted to anything that could be considered “intercourse” and the number of times this happened can be counted on one hand (so to speak). To be perfectly clear, it was mostly mutual masturbation and some brief mouth-genital contact. The last time anything like this happened was when I was around 11 or 12 years old. I’ve been staunchly heterosexual since.

She made some very painful disclosures during our conversation regarding a previous relationship (nothing same-sex related, though) and I’m feeling as though I’m being dishonest by not showing similar honesty. At the same time, I wonder if I’m being ridiculous about something that, I feel, has no bearing on the person I am today or my current sexual identity. Of course, I also fear her reaction somewhat, although she is amazingly understanding and open-minded, so I’m less worried on that score.

Should I just come clean or decide once and for all that some weird experiences when I was twelve might as well have never happened and put it from my mind?

You are being ridiculous. Do kids do anything BUT hump on other kids of all genders? When? Literally, at what time do they find the time to do other things, amidst all the humping they have to do? I have to say that if anything, the fact that something so super normal is causing you this much anxiety makes me wonder if you’re as, er, staunch as you say. But now I’m being a little unfair. Maybe you actually didn’t know that every other kid was feeling on every other kid all the time, forever for eternity except for the time they took off to feel on themselves, and you’re really wondering if it counts toward your “number” or whatever. I’ll buy that, people never talk about this shit at, like, work retreats or whatever, and I’ll bet dudes talk about it even less than never. So. No, you don’t have to tell, because it’s literally NOT A THING. It’s like telling her you practiced making out with a pillow. If you want to tell, and your girlfriend thinks it’s inherently weird that it happened/makes you gay, she’s bananas. If you tell and your girlfriend thinks it’s weird that you think it’s a big deal that you needed to have a Capital T Talk about, then I think she’s kind of right? Consensus: Don’t tell, it’s weird.

Previously: Deafening Tampons, Spring Breakers, and the 26-Year-Old Virgin.

A Lady is one of several rotating ladies who know everything. Do you have any questions for A Lady?

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