Hookup Help: Asking Your Crush on a Date

Q: Dear Holly. I’m a student at a small college in a small town and it’s hard to meet women. Well, it is for me because I’m shy and don’t have a lot of experience. There’s a girl I see at least once a week in the library or coffee shop. She’s super cute and is usually alone. I’d really like to ask her out. I’m thinking maybe she’s a shy person too. I wish I knew what she was studying just so I could see her more. How do I approach her and what should I say? – Allen

A: Dear Allen. You have a crush, that’s for sure. It’s easy to crush on someone from afar because you don’t know much about them, but the problem that can happen is that you develop a fantasy about what she is like that may not be close to her reality. Let’s get the ball rolling, Allen.

It sounds like you have at least one opportunity a week to approach her. Notice, I didn’t say “ask her out.” Because you are shy and she may be too, the best way to let something happen is naturally. Let’s go with the coffee shop, since the library promotes silence and studying. The next time you see her sitting alone, walk up and ask if she minds if you sit down beside her. You could also ask a general question about directions or what not, but that might stop things dead in their tracks. Maybe reading something you can ask about. The idea is to get the conversation started and try to keep it going… questions do that. Maintain eye contact as best you can… it’s the easiest way to connect with someone immediately.

I don’t want to be a downer, but you have to be prepared for rejection. It happens and comes from pretty women who get hit on a lot. That’s why if you keep it casual, you may actually have a chance to converse and get to know her before a date even occurs. And remember, you know nothing about her, so she may not even be a suitable match.

Go for it, Allen! You have nothing to lose.

I also like to remind readers that every time you approach a woman or ask her out, no matter the outcome, you are building dating confidence. And confidence is very attractive!

Hookup Help is a Q&A series. If you want advice or a female’s perspective on hooking up, online dating, relationships, or sex… we want to hear from you. SUBMIT YOUR QUESTION, and who knows, you may appear in the next Hookup Land newsletter. -xo Holly and Tia

Ready to Find Local Hookups?

Explore the Best Hookup Sites for Getting Laid in 2022.

Find Hookups Now

Tell us what you think

Notify of
Inline Feedbacks
View all comments