There are arguments to be made both ways on when to meet up for the first time with someone you’ve met online. Getting together right away will dispel all the fantasies that you can build up when you haven’t met, and if you meet earlier on, you’ll know if there’s chemistry or not, which you can’t tell from an online relationship. On the other hand, building a relationship via email may be more comfortable and easier, especially for the socially awkward, and you may even be able to get to know someone better online than you would in person.
On the whole, though, doing it sooner rather than later is better. One, you need the practice (have I said that enough yet?). And putting it off too long makes it that much harder to do because you have more invested in it working out. So after a couple of emails back and forth, and maybe a week or two has passed since your first email, suggest getting together. Probably not a great idea to suggest getting together in the first email. That works fine for some women but for others, they’d rather they had a better sense of whether you’re a psycho or not. For a woman, there are safety concerns, so don’t suggest picking her up at her house or dropping her off after your date. She doesn’t want you to know where she lives!
May I engage in a brief tirade? What is it with men who think they can walk up to a woman in a deserted parking garage and ask her the time and get miffed when she doesn’t answer? Does it really not occur to men that she isn’t a snob, that she’s protecting her safety? Men need to be aware that when women go out in the world, as sad as it is, they think about their safety in a way men are free not to. Most women will not walk down an alley in the middle of the night. Most women will not be willing to engage in chitchat with some guy in an isolated area, like a bus stop late at night. Most women do not want a stranger they met online to know where they live or what their last name is--at least not at first. Be aware of these security issues and don’t cross the line. Let her lead the way. Let her be the first one to suggest going to your house or her house, etc.
On Tuesday I’ll wrap Where to Meet Her with speed dating and a few other suggested places. I’ll write more about the “Dating Game” and first dates starting next Friday (what to wear, what to talk about, etc.).