A woman wrote to me wanting to know if she should wink at a man on a dating site.

Well, I’m a big believer in letting the man do the work of winning us over. But, in the usual way, when you are both physically in one place, I also teach women to give the man a clear message that it’s safe for him to approach. Men are pretty scared of rejection (unless they’re really smooth with women) so they need about a 95% sure sign from you that it will be okay to approach you.

On dating sites, I think the best way to handle this is to go ahead and do the wink thing. Because there are so very many women for him to check out, a wink will at least get him to your profile page and photo (photo being the most important thing because men are so visual). Then, do nothing more until he responds with an invitation for interaction.

If you wink and he doesn’t respond, it means only two things: 1) He hasn’t been on the site or, more likely, 2) he took a look and isn’t interested. If you wink again, or approach in any way, you’re breaking all the rules by being needy or aggressive, both a turn-off to men. You want him to stay in the masculine role. The moment you start pursuing him, you have taken over his role. If he is interested, he’ll be lazy because you’ve basically told him he doesn’t have to do any work to win you over. There’s no fun in that. Women who have forgotten how to enjoy being a woman don’t realize how delicious and juicy it is to be pursued by a man who is working hard to win your affections.