Hookup Help: Tips for Dating Shy Women

Q: I met a woman in school and we’ve talked a couple of times, but she’s always a little awkward. She’s very beautiful and extremely smart in class but very shy. She turns red when she has to speak out and never sticks around for discussion groups. I’m working my way up to asking her out, but don’t want to blow it… if she accepts. I’m not used to dating shy women.

A: Just because a woman is stunningly gorgeous or confident in her work, it doesn’t always mean she’s a dating tigress. I’ve got plenty of hot female friends who are shy and timid when it comes to dating… sometimes it’s a personality thing and for others, it’s because she’s been burned one too many time. It could also be that she expects the man to make the first move. Whatever it is, it can be confusing for guys, wondering what the best way to approach and ask a woman out is.

Tips for Dating Shy Women

Nothing turns a shy girl off more, than a guy who’s trying to force her to open up or do things she’s just not comfortable with. If you really like her, then the wait will be worth it.

Take notice of things that make her shy. Is she more relaxed in a one-on-one environment? Does she prefer an outdoor setting to a packed restaurant? Realize where she feels most comfortable and spend time with or approach her in these locales.

Shy women will respond to you opening up about yourself. By sharing some intimate details, a date will see that you trust them and will feel that you can be trusted as well. Nice guys can finish first.

No grilling or twenty questions, please. Ask her things that are specific to her but not too intimate, so she’ll feel at ease talking with you and not anxious about letting you in too much. Attentively listen to her responses and bring these back in later conversations.

If she does drink alcohol, you can offer a drink. Her shyness may be mostly nerves and one drink can calm this physical anxiety fairly quickly. Of course you don’t want to push booze on a woman, so act responsibly.

Her shyness may be part insecurity. Some beautiful women don’t see themselves the same as others do. Shy women don’t always know how to take a compliment and may be dismissive or self-deprecating, but don’t let that stop you… just don’t overdo it, or she’ll feel embarrassed.

A shy woman may feel uncomfortable about making decisions about your date or expressing her views. Don’t be afraid to take the lead when planning or guiding your date along. She’ll appreciate this and will slowly get more involved by expressing her preferences.

Any tips you can share?

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 HERE, and who knows, you may appear in the next Hookupland newsletter. -xo Jenny

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