One of my pet issues—constantly reiterated on this blog and in personal conversations—is that if you would like to get a date, and you are not currently getting dates, and you are not asking people out, you need to ask people out.
I have grudgingly accepted that a bunch of people will not listen to me about this, so here is my second plea: if you are a shy nerd, please check that you are not accidentally rejecting people hitting on you. (For some reason, this is particularly common among people who are attracted to women. Lesbians, heterosexual men, I am looking at you.)
In general, people do not approach someone romantically by going up to them and saying “you are wildly attractive and I want to take you out and then make sweet sweet love to you all night and then elope to Vegas and be married by Elvis in a drive-through chapel.” Instead, there is a gradual process of escalation. People do a plausibly deniable expression of interest, and then wait to see how you respond.
Unfortunately, shy people of the world psych themselves out about this. They don’t believe anyone could actually find them attractive. And they end up accidentally expressing a lack of interest in the people they’re talking to.
Talking About Things
Flirting person: blah blah blah topic of mutual interest blah blah
Shy person: oh my god a hot person is talking to me what do I do what do I do what do I do I’m going to say something stupid and then they’re going to hate me forevere and mock me with all of their hot friends and I’m going to have to lie under the covers in my bedroom for the rest of my life because whenever I emerge I will be the subject of vicious mockery
Shy person: [says nothing]
Flirting person: Oh, huh, I guess they think I’m boring, because they’re not saying anything. :( It’s too bad, they’re really cute and interesting and I wanted to get to know them. [goes away and talks to someone else]
Instead: I myself have struggled with not being able to say anything in front of an attractive person because I’m so worried that everything I’m saying is incredibly stupid. I usually fix this problem by going “I keep failing to say anything because you’re so attractive that I’m scared everything I have to say is incredibly stupid,” but I understand that this is one of those social moves that makes people complain that I am immune to fear. But please try to say something. If you don’t say anything, it is subtextually saying that the person is annoying and boring and you want them to go away. Shy people who do this, you may have been rejecting people who are into you in a pretty emotionally crushing way
It may help to come up with a set of inoffensive scripts. For example, if you are curious about something they’re saying, you can ask for elaboration. “Wow, that’s fascinating, tell me more” is always welcome.
People Leaving Conversations You’re In
Flirting person: [gets pulled into a conversation about programming or something]
Shy person: oh no they hated me, I said something dumb and that’s why they’re going off to talk to someone else I need to melt into the floorboards I am never going to talk to them again
Flirting person: [a few hours later] Hey, I never talked to Shy Person again at this party. It’s too bad, they seemed cool.
Instead: it is fine to reinitiate conversations with people at a party, if you got along with them the first time. People are capable of making excuses and saying that they’d rather go circulate. Try waiting a bit (maybe half an hour?) and then joining a group conversation that they’re part of. If they get pulled away a second time, wait until they strike up a conversation with you. (This is a conservative approach which will not make you come off as a stalker; of course, if you’re less anxious, you can reapproach people more often.)
Responding To Messages
Flirting person: [messages Shy Person on Discord]
Shy person: what do I say what do I say what do I say oh my god [drafts message, deletes it] [drafts message, deletes it] [drafts message, deletes it] everything I have to say is incredibly stupid I am going to have a panic attack I am full of waves of shame I can’t even bear to look at this message I am going to run off to the desert and become a stylite and communicate exclusively in cryptic prophecies [overwhelmed by shame to the extent that they quit social media altogether and wind up successfully running a marathon out of sheer boredom]
Flirting person: Oh, I guess I misread Shy Person’s signals. :( They really seemed into me, but that must have just been wishful thinking. I wish I could get to date someone as cool as they are, but probably they’re not interested in someone lame like me.
Instead: type up a message even if it sounds stupid, leave the message in the box while you go have your panic attack, and then impulsively hit “send” after your panic attack. This does mean that “person X is typing…” goes on for a really long time but the other person is only going to notice this if they’re already obsessing about you so I think it is fine.
Physical Touch
Flirting person: [touches Shy Person’s shoulder casually]
Shy person: PHYSICAL TOUCH!!!! PHYSICAL TOUCH!!!!! THIS IS NOT A DRILL!!!!! THIS IS NOT A DRILL!!!!! I AM BEING TOUCHED!!!!! BY A PERSON!!!!!! THE TOUCH BARRIER HAS BEEN BROKEN!!!! WHAT DOES THIS MEAN!!!!! WAS IT AN ACCIDENT!!!!!!!!
Shy person: [looks incredibly anxious and uncomfortable]
Flirting person: Oh FUCK I just borderline sexually harassed them! That is incredibly awkward. I hope they’re not mad at me. I better pull back and not touch them anymore.
Instead: I admit that I’m asking for a lot here. If you’re genuinely anxious and uncomfortable, you’re going to have anxious and uncomfortable body language—and other people are going to parse that as “I don’t want to be hit on” and not “I don’t want to fuck this up.” Most of us are not Oscar-winning actors and have a hard time hiding our feelings. But you can at least try to casually touch them on the shoulder back?
Being Asked Out
Flirting person: hey, do you want to go out this weekend and see the new Marvel movie?
Shy person (to themself): well, obviously they’re not interested in me as a person, because no one is interested in me as a person. And I don’t like Marvel movies. So I should say ‘no.’
Shy person: No, I don’t want to.
Flirting person: Dammit. Date plan thwarted. I guess they’re just not that into me.
Instead: I can’t believe I’m saying this, if someone you find attractive proposes a one-on-one hangout, you say yes. You don’t say “actually, I’ve already seen that movie” or “I don’t like rollerblading.” If you object to the plan, you suggest a different plan which you prefer. “I can’t get barbeque because I’m vegan, but there’s this cool little Indian place near my house.” “I’m busy at that time— can we do Thursday night?” If you don’t do this, they’ll assume you’re politely rejecting them.
In conclusion: flirting with shy people is a nightmare. They don’t reciprocate any of your overtures, you have to message them five times to get an answer, and their body language is so uncomfortable that it makes you feel like a sexual harasser. And then once you actually get around to asking them out it turns out they’ve been in love with you for four years. I hate it. If shy people weren’t so damn cute I would swear them off and date only Chads from now on.
> Unfortunately, shy people of the world psych themselves out about this. They don’t believe anyone could actually find them attractive. And they end up accidentally expressing a lack of interest in the people they’re talking to.
This isn't really accidental in any way. If you have a culture which pushes memes like "objectification of women bad", then either no one is going to listen to that message (in which case, why say it?), or a bunch of males (and lesbians I guess) _will_ listen, infer that perceiving women as sex objects (which is what 'attraction' is - obviously women are also human, but there's also _that_) is considered objectionable, be unable to actually alter their perception probably, but be able to suppress any possible reactions, as if they were asexual.
"THE TOUCH BARRIER HAS BEEN BROKEN!!!! WHAT DOES THIS MEAN!!!!!"
If you're male and low status, and the other person is female, it means, "Watch out—you may still be accused of harassing or assaulting her, get regularly beaten up in prison for the unmanly deeds you've been accused of, and rot in there".