Insecurity and Awkward Encounters (Cats, Colds, Etc.)

by A Lady

I’m 25 years old and have a great job, great friends, and a great relationship with my family. I live in my favorite neighborhood in my favorite city in the world. I have a lot of hobbies and interests and I’ve finally learned to enjoy working out. I have a good life, is what I’m saying.

The problem is that after a painful breakup in the spring (and even a little before then), I’ve realized that I’m deeply insecure when it comes to men. This leads me to make terrible decisions, like pre-emptively rejecting guys I actually really like because I’m so scared they’ll reject me, or dating guys I don’t really like for way too long because any male attention is better than none. I can’t act normally around men — I feel sometimes like a dog begging for scraps. I guess at heart I’m terrified of ending up alone, even though, as a feminist, I’m quick to say that being single is not the most horrible thing that can happen to a woman (and I believe that! Just not for myself).

So, I decided that I wouldn’t date anyone until I could work that out and 1) become truly happy with my single existence, and 2) learn to see men as human beings and not as the owners of my self-worth. Unsurprisingly, it’s a lot easier said than done. As a small example, a man at work is starting to show interest in me, and even though I know he isn’t right for me, I’m finding it hard to discourage him.

Do you have any tips? How do I do this hard work?

Dudes! Can’t live with them, can’t kill yourself because then how would you meet dudes?

How you become happy with your single existence: Go to the spinster tent — you know, the purple and gold one on the lushest hillside, appointed with tapestries and rugs lovingly woven by generations of our foremothers — and spend your days gardening and reading poetry, and then dance joyously into the night to the sound of a thousand timbrels.

No, screw timbrels. Screw destructive Eat, Pray, Love vagazzlery. You can’t catch happy, even in India, and you can’t hide from sad. Happy is a feeling, not a status. It arrives more often and lingers longer when you aren’t afraid of it leaving (a lot like dudes, go figure). Everyone, seriously, stop sweating happy. Let’s try “dealing.” Why do you have to be truly happy being single? Being single can really fucking suck sometimes. (Everything can, differently! Being alive: No one’s gotten it right yet.) Feel lonely! Dislike that feeling! Crave even imperfect romantic attachment!

But do — do — find a way to take it a little easier on yourself? If someone told a friend of yours she was like “a dog begging for scraps,” you would say that person was. . . a jerk? A bad, bad jerk. There’s a bad, bad jerk in the corner of your head, and you have to find a way to leave the room when she starts to run her mouth. Worst case scenario, you are a genuinely rotten and pathetic person (you are not. Pretty much everyone is just normal). OK. Well, you still have to haul your rotten, pathetic self through space and time somehow, and dwelling about how much you suck isn’t going to help you do it. PS, I have a jerk in my head too! He mostly bothers me about work-related stuff, and his name is Alan. I literally sit around my office telling an imaginary person named Alan to stuff it. And I’m not that good at my work right now! But fuck if I’m gonna let Alan get nasty with me about it — what has HE done lately? Stuff it, jerks!

Oh but the jerks in our head! Rivaled only by the jerks in the real world. Yes. The glazed eyes of people who want (or, god, worse, DON’T WANT) to fuck us are a warped mirror. You’ll either grow out of the obsessive primping before it or become a Real Housewife, but who wants to wait to grow? What can we do NOW NOW NOW to care less about whether boys think we are pretty or not? Normally my advice would be “I dunno, just try to have ugly friends so you are always the pretty one?” but you said something smart that I want to come back to: that you want to “learn to see men as human beings.”

That’s why I wonder if your “no dates until I transcend” policy is the right one. If it sounded like you were getting involved in totally off-the-grid self-damaging stuff, maybe, but you sound pretty normal-crazy, and even if you didn’t do anything I think you’d hit the standard giving-less-of-a-fuck milestones which occur in ages divisible by 6 or 9. In the meantime, though. . . men ARE human beings, pretty typical ones, mostly, and I’ve found hanging around them is a good way to get a sense of that. Why do you have to discourage this dude who seems into you at work? Why can’t you just relax into the idea “I am being flattered. Flattery, unsurprisingly, is pleasant”? Yeah, yeah, then he asks you out, then you say, I don’t see us like that, then he says, but you let me say nice things to you, and then you say, yeah, it’s nice to hear nice things! And if he’s like BITCH LED ME ON, well, then you’ll know you were dealing with a jerk. Name the jerk in your head after him!

What you’re really asking for is a source of validation other than — and more powerful than — the validation you get from dudes. Maybe, if you tried really hard, you could care less about dudes and more about being Best at Work, Knower of Best Bars, whatever — there are infinity unsuccessful ways to try to live in other people’s minds, and maybe one of them will work for you. I don’t know, though, I think you need to learn that dudes don’t know what they’re talking about — in an adorable, chaotic, human way! — and I feel like talking to them is a good way to learn that. Engage in good faith and men will lose their imaginary power — and gain a whole new charm? — the more you are in the world with them, ask questions, challenge, coax, flirt, annoy. That’s the “work,” being in the world and asking why? how? why? you want to WHAT? over and over like the spiritual toddler you are. Upshot: I would say don’t touch a dude’s penis until you have made a point of asking him five involved, intrusive questions (“do you think I’m pretty?” doesn’t count). Baby steps, girls! Baby steps.

Here’s the short story: I have a new friend who I’ve been flirting with like crazy. We just basically admitted we’d like to hook up sometime and traded dirty stories — what we’ve done to people, what we’d like to do to each other… he was a good bit more experienced than me, but whatever, I am a cute, confident young lady, that just sounded like a sexy challenge!

So anyway, this was finally a time we could both go out. I had a tiny little cold, but seriously wanted to impress this dude, like, as soon as possible, so I loaded up on cold medicine and headed to the bar anyway. And then, when he finally made a move to kiss me goodnight it went well, I was so hyped I just went ahead and asked him to come home with me. I have never had the guts to do that before, and I should be feeling kind of smug with myself, because he was totally into it.

But things went kind of funny after that and I maybe lost my cool a little. My cat was obnoxious. My apartment was messier than I thought. My underpants were mismatched. I ran into a door. And maybe it was the cold, or the medicine, or how late it was, I don’t know … but I think I kind of sucked in bed once we got down to it! I was way more dry than usual and kept apologizing for all the stupid stuff I should have just ignored, and I may have admitted I’d never just asked a boy back to my apartment like that before, and the whole time he was telling me how pretty I was and working really hard to give me orgasms and telling me I could be as loud as I wanted, and he was super well endowed and I didn’t even have any lube to offer and I didn’t end up getting him off at all, even though I kind of tried!

Eventually, he just ended up saying it was OK and spooning with me until we fell asleep and then I had to wake him up at an inhumanly early time and kick him out so I could leave for work. He was super sweet and kissy and told he’d be thinking about me all day when he left, but now he’s not talking to me at all, and we’ve been chatting every day, like, non-stop up until now!

So what happened? Do you think he is just totally over me because I was so awful in bed? Can I salvage this somehow? I’d really like another chance at banging him … I mean, just thinking about him usually gets me way more wet than that! Is it super crazy to try and let him know that this was totally not normal and I was probably just sick and nervous? Should I leave it alone? And was it totally unethical to expose him to cold germs?

YOU are the cutest. You are the actual cutest person, nice try Zooey Deschanel in New York magazine. Cold germs! Unethical! Is he in an iron lung? Is he the president? I’m just disappointed you didn’t play up the stuffy “Ib so snick, wilb you take goob care of me?” thing. By “mismatched” underwear do you mean “tattered, blood-stained” underwear? When you say “walked into a door,” do you mean “fell off a stool in a crowded, fancy hotel bar and took down an old lady with me? And I wasn’t even drunk? I literally just can’t sit?” I mean, your apartment was messy? Oh the utter FILTH I have stumbled through blissfully, hoping to bang. Like moldy old open Chef Boyardee cans are just the BEGINNING. It’s like you are a cute, slightly spacey Maria as played by Julie Andrews in The Sound of Music and the rest of us are that actual live pig they shot in Cannibal Holocaust.

Anyway, though, whyyy diiidn’t heee caaall, as the song of the spheres goes? I mean yes, YCRM but also. . . this is just not adding up. Here are the possibilities.

1) You are not telling me something. Letter writer? (Stern Look) LETTER WRITER? LETTER ANNE WRITER, is there SOMETHING YOU WANT TO SAY TO ME? (Anne is everyone’s middle name.)

2) He was looking for some uncomplicated private-touching and just has thousands and thousands of options and the Nyquil Vag made him be like WHY BOTHER, THIS IS DIFFICULT. The context and the after-the-fact kissy-face-wuv-you-awww make me think no, but I don’t want to rule anything out. Maybe he’s married or has a girlfriend and feels bad. Or god, I don’t know, can you see him from where you’re sitting? If not, maybe he’s dead.

3) MOST LIKELY he has two feelings, or even more. Here: “Ahhh, I ALSO HAVE FRIEND-LIKE with this chick! That might get weird! But awesome! But weird! Should I have cooled jets a bit? She said she didn’t do this sort of thing and then it was fun but also a little awkward and what if she thinks I’m bad at stuff and she didn’t seem THAT into it but then she kept saying she was, just that she was sick? But she has a cat and I’m allergic SERIOUSLY WAIT, WHO HAVE I BECOME THAT I EVEN THOUGHT ABOUT THAT? My father is looking so frail these days. He says he’s proud of me, but there’s so much he’ll never know. Can I still dirty talk her on Gchat? Or is that, like, now she’s over it because no one came and she will be like GROSS I HATE YOU? Would that still be hot? If I started doing her all the time, could I not do other people? What about that that person, outside my window right now in the. . . is that what’s called a jumpsuit? I’d jump that. . . suit? No, seriously, could I never do whoever that particular girl is outside right nowww . . . OK, she finished walking by. Yeah I should definitely chat work girl oh fuck I just remembered the part where the cat attacked my balls oh man she’s just gonna be like, it’s that weird guy with a cat on his balls right? Fuuuck fuck fuck I hate this tacos tacos I hate this.”

Do you see this mess? Someone needs to take the goddamned reins over here, and it doesn’t even matter how or where you steer them. Here. I have a funny story about sort-of STDs that you are going to tell him, it’s going to make things great. It’s perfect, because it gives you a chance to acknowledge that you did, you know, stuff and talk about more stuff, but it’s weird enough to maintain plausible deniability if he’s like, who are you?

SO. Did you go down on him? Because I actually know a dude (FOR REAL, I know this dude, this is not an urban legend, we talked about this over pastries in the real world) who thought he had chlamydia, and then the doctor called him back and said “you have tested negative for everything except for um, influenza. Of the penis.” Dick flu, you guys. Dick flu is a thing, and my friend got it. And thought it was chlamydia. Anyway, so you might have given him dick flu, and you should apologize ahead of time so he doesn’t worry it’s chalmydia. Or if you didn’t go down on him, say “well it’s a good thing I didn’t go down on you because here’s a story. . .about dick flu.”

Previously: Dating Ethics, Drink-Legs, and Smell Interference.

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

Photo via Flickr