Dear Great and Powerful Jono,
Let me just start by saying this: pizza.
Now that I have your attention, I have a totally life-altering and completely original question to ask you. I know. So interesting. I bet you're just bursting with... interest right now.
Anyway, so there's this guy I have a crush on. (See? Groundbreaking stuff.) By "crush," I basically mean he's a male person whom I find attractive but have never actually talked to. He's said words to me (well, WORD, anyway). This boy, whose name throughout this story shall be WhoBob WhatPants, said "hi" to me one time as he walked past me, but I responded by waving with a fork and what was probably a really awkward-looking, full-mouthed smile. At another time, I was sitting at a table way in the back of the cafeteria, alone, and he sat at the same table randomly. At this point, not even an awkward fork-wave-thing was exchanged. I just looked at anything other than his face the whole time out of sheer and utter fear. THE. WHOLE. TIME. It was very slightly terrifying.
Now, I think I have WhoBob's interest, and have had it since I transferred to my new school, but every time I let myself believe he's watching me, I end up psyching myself out. As I've never had any sort of experience in the dating department and suck at feelings and junk, I'm worried that I'm just imagining WhoBob's intrigue, or I'm so socially inept and unaware of his attraction that he's mistaken my ignorance and hesitance to do something as a sign and I've missed my chance to make a move. How do I start a conversation without coming off as a whack-a-doodle nutjob? How long do I have before I miss my window of opportunity, if it's not already closed? From what I can tell, he seems to be the shy, Oh-my-gawd-a-girl type, so should I try make a first move? And again, how do I do that without exploding from my intense boyilikephobia?
Furthermore, did the chicken or the egg come first?
Extremely Long-Winded Girl
Okay, first of all, you seem worried that you're going to suck at talking to shy goony dudes, but I think you'll be better at it than some bubbly, outgoing girl would be. You'll forgive his awkward silences and awkward... talking... instead of getting offended or thinking he hates you, because you'll understand where he's coming from. Second, you've never missed your window of opportunity unless he's married or he lives in outer space. Problem is, he might think you don't like him, because of the encounter where you wouldn't make eye contact—that was his attempt at making a first move. It's just that he didn't have any moves planned after that. He moved his king's pawn to e4 and then hid under the table. It's going to be up to you to help him along. (Third: the chicken.)
1.) Doll yourself up.
Look, I'm not saying that you need to slather yourself in makeup until you look like a sexy clown and go "Please objectify me, tee hee!" But you should begin by taking whatever attractiveness steps you're comfortable with, because anything that makes you feel pretty and likeable will also enhance your confidence and make you more outgoing. Furthermore, the dude you're talking to may have a bad case of The Shys, but he also suffers from Male Pattern Boyness, and seeing a pretty girl will help override his innate derpiness. Tasteful makeup will have a more desirable effect than a stinky sweatshirt that says SWEATSHIRT on the front. (If you're a dude trying to follow this guide, you can... I don't know, put on a new hat or something. Just make sure you've taken a shower ever.)
2.) Start with eye contact.
Okay, I know you guys are getting tired of my saying this and must think I own stock in an eyeliner company or something. But seriously, even if you and the dude already make eye contact all the time, it's important to start this encounter with a meaningful glance. It changes the subtext of the whole conversation. If it's somehow possible he doesn't realize you're into him, this should help clarify that. So look at him for a couple seconds, and then make your approach; one of three things will happen.
- He maintains eye contact. Good. Yes. MISSION IS GO. Proceed to #3.
- He keeps eye contact for a moment, then looks away. Acceptable, because he is a shy goon. MISSION IS STILL A GO. Proceed to #3.
- He instantly glances away. He's either super duper shy or not interested. If you can't get him to look at you, ABORT ABORT. (Well, you don't have to abort, but understand that you're going to be doing most of the heavy lifting in this conversation, and he's mostly just going to stutter and look around at the ceiling.)
3.) Say a thing.
Any conversational opener will do. Here are some generic examples:
- "What are you up to?" if he's writing or studying or something. Do not ask him what he's up to if he's literally just standing there and not doing anything, because he will say "nothing" and you'll say "oh" and you'll both stand there in pointless silence for the rest of eternity.
- "Can I borrow (a pen/your phone/whatever)?" Asking someone to borrow a phone, because yours is dead, is a tip given to me by an ACTUAL ALIVE GIRL. Do not ask to borrow someone's phone if you are standing there holding your completely functional phone. Do not attempt to improvise this opener ("Can I borrow your p... puh... paaants?").
- "Mind if I sit here?" if you're in the cafeteria or on the bus or whatever. Do not ask to sit here if you are both standing around because then you'll be conversationally obligated to sit on the floor and you will look stupid.
Continue saying things, regular things. Don't worry about being completely sexlicious. Just say whatever (but don't bring up his shyness; some people react to this badly and just become even more shy).
4.) Say or do a flirty thing.
All of this has been setting up a Flirtatious Thing, one that can't be misconstrued as simple friendliness. Do not lead with the Flirty Thing; only after chatting for a little bit should you smile, maintain the eye contact, and do something like:
- Touch his elbow. This is a nice, safe choice, as the elbow is perhaps the least sexy joint in the body, except, like, the interphalangeal joint (but it's unwise to flirt by caressing his toes).
- Tell him he has really nice eyes. Another safe choice, because all people like to think they have nice eyes, so he won't be like "No I don't!"
- Make him lean in. Lean in and say "Hmm?" so he'll repeat what he just said, which invites him to lean in too. Don't try this in the dead silence of the library, or repeat it too often, because he will simply assume you are deaf.
- Pick a piece of lint off his shirt. This is something girls do. Is the lint imaginary? I have no idea. The ways I would mess this up are endless so I've never tried it.
The long term goal is to ask him on a date or at least get more overt about the fact that you like him, but you don't have to worry about that yet—right now, the goal is just to get the two of you at a table, talking instead of not talking. Soon, somebody is going to have to ask somebody out. Until then, just establish that you don't actually hate the guy, do actually like talking to him, and intend to talk to him even more times.