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Q: I’ve been online dating for just under a year and have met a couple women, but nothing really came of either encounter… not even a one night stand. But I didn’t mind because I’m looking for something more serious. I’ve been single a long time and think I’m ready to get involved in a long-term relationship. So here’s the latest: I met (only online so far) a woman who is beautiful and seems to have it all together. I read her profile carefully to send a good first message. Most of my messages don’t get responses, so I’m trying a little harder these days. After a few days, she responded! I was thrilled, but that was a month ago. We send messages through the dating site every other day or two, and they are even getting a bit flirty. I’ve been waiting for her to suggest we meet in person, but nothing so far. I don’t want to be pushy. Should I just go for it. I’m scared of scaring her off. -Ryan

A: Hi Ryan. Your question or dilemma is a common one in the world of online dating. And because you are relatively new to internet dating, it can take a while to get a handle on what works best, although you really never know what to expect after you press send. I like that you mention reading a woman’s profile carefully. Sometimes there is a lot revealed between the lines of a dating profile that can help save you the time of meeting an ill-suited person. I always try to remind my guy buddies that it’s worth the initial effort of crafting a great first message to up your chances of a response.

I had a similar experience, but my back-and-forth messages lasted three months (he was away on business when we met online). I was head-over-heels by the time he got back, but the reality was only a disappointment to the fantasy I had created. This debacle taught me that waiting too long to meet, can end something before it really begins.

If your conversation has been going on for a month, it’s time to meet. And… you should initiate. Sorry, Ryan, but most women still like men to make the first move, even online moves. Obviously she’s interested, but just as a warning: there’s a small chance she could be a “tire kicker”, a woman who only engages in online relationships for whatever reason. You’ll know soon enough if you ask her out.

Remember men: there are plenty of other men pursuing online. If you sit back too long, your lady interest may be scooped up by some lucky guy.

Read: First Online Message Tips

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

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