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Hookup Help: How Long to Message a Woman before Meeting in Person

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Q: Dear Jenny. When I meet a woman on a dating site, I’m never sure how soon to bring up the idea of meeting in person because I’m afraid to scare her off. Should I wait until she suggests it? I’ve been having a back-and-forth conversation with a woman for about a month and want to ask her out. Should I just do it? – Brent

A: Hi Brent. This is a great question, and one that many people struggle with, especially shy people. The short answer is: go for it because you have nothing to lose. If she wants to meet you she will, and if she’s just kicking the tires you’ll stop wasting your time.

How long a person waits to meet someone in person varies and really depends on a person’s dating confidence, online dating experience, and their comfortability. I have girlfriends who will either message or receive a message and want to meet that person immediately. This quick-date method works for many because you don’t have time to build any kind of fantasy or unrealistic expectations. And no matter how great you hit it off online, chemistry really can’t be gauged until you meet face to face.

Other people I know want to message back and forth – like you are – for weeks to see if there are any red flags or deal breakers. There are women (and men) who are happy just to chat with people online, but are not all that interested in actually meeting IRL for a variety of reasons (they are attached, they travel a lot, etc.) This can be disappointing.

I recommend somewhere in between the spectrum. If you like this woman, you should ask her out. It’s been a month, and it’s my belief that a man should ask the woman out on a date. It’s not that I’m old fashioned, but men need to hunt. It’s a gender thing… and women want to be asked out!

Use cues you’ve garnered from her profile and your conversations to plan a date unique to her. Best of luck, Brent!

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 Hookup Land newsletter. -xo Jenny

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