A Shy Girl’s Guide To Hitting On Guys

Dear Shy Girls,

Yes you, the ones who refuse to try online dating but complain guys are never interested in you. I’m talking to you. I get you. I understand how even the idea of approaching a strange man that you find attractive makes you blush and shake your head furiously. Please, understand that I’ve been there. I’m here as your Fairy God Sister to impart on you wisdom that I’ve collected in my years as a shy girl trying to break out from the shadows.

1) The Direct Approach
Scenario: Tall, dark and handsome is sitting at the counter at your local bookshop/coffee shop/bar. Let’s call him TDH and he’s, for one moment, not surrounded by his equally tall, dark and handsome friends. This is your moment. You stand next to him, glance at his glass/cup/book and ask what he’s drinking/reading.

Shy girls, please bare with me! Stop shaking your head so furiously. Think for a moment how he is going to respond. He will either answer by telling you about his novel/coffee/beer and start a conversation or he’ll respond and go back to not realizing you ever existed. No human would humiliate someone for asking a simple question. I mean, think about it in reverse, would you laugh in a guy’s face for asking what you were drinking/reading? So walk up to TDH, say, “What’s that? It looks good” with genuine curiosity and see where it will lead you.

2) The Elementary School Move

Scenario: TDH was just spotted walking into your class. You had no idea he was even into historical literature, but there he is, looking all TDH. Know what you need to do? You need to sit next to him.

Your head is going to fly off if you keep saying no that much, Shy Girl. I’m going to drop a knowledge bomb on you right now: The more you put out there, the more you’ll get in return. If you study hard for a test, you’ll get a good grade. If you make the first subtle move, you will get noticed. Now, what I’ve done in the past to move things along is a bold girl move. I like to pass notes to the guy — a la elementary school. Writing down fun quotes from movies can sometimes work. A little Step Brothers, maybe? This move obviously has more at stake. The guy could not recognize the quote or he might not be interested. The worst that happens is you get a weird look, promise.

3) The Gum Trick
Scenario: You reach into your purse for a piece of gum. TDH is mindlessly sketching Game of Thrones characters in his notebook. Ask him if he wants a piece. Just go for it. Think of it as the equivalent of saying, “bless you,” after he sneezes. It’s really not that bad and it’s hardly a huge step. This is the baby of baby steps and the worst that will happen is that he will say, “no thank you.” But at least he’ll see you as considerate and heck, maybe he’ll take you up on it.

4) The Double Dare
Scenario: You’re out with your friends and sort of bored. Solution: a low stakes game of Truth or Dare (or scavenger hunt if you have some time on your hands). You have a friend dare you to approach the guy across the room and snag a pic with him — or whatever the dare may be — and thank him for his cooperation. This is a very fun game that will end in a good time whether you get the guy’s number or not.

Welp, now you know some of my tricks. I couldn’t tell you my success rate but I can say that you will remember more fondly the things you tried and failed at than the things you wish you tried. So keep reminding yourself that sitting next to a guy and asking what’s in his cup is not going to end in you being drenched in pig’s blood at the prom. Be confident! You’re amazing and can get any guy you want as long as you try. Go get ’em!

Love Always,
Your Fairy God Sister

Filed Under