This weekend, I feel like I took some good small risks. I had a dinner party and invited a mysterious guest — a person I've only met recently, although we had something of an instant connection. Another risk: giving him a spontaneous hug at a certain point in the evening…and not pulling away a few times when our knees touched during the meal.
Here are my guidelines for how anyone — even the shy — can take more flirtatious risks:
1. A series of small risks that slowly lead somewhere may be more productive — and less potentially emotionally debilitating — than taking one HUGE risk. For instance, the two small risks I took — inviting this man to my dinner party, and giving him that little hug — helped us feel each other out (to say nothing of feeling each other UP) without either of us being pushed too far out of our comfort zone. Had I taken a bigger risk — like drinking too much at his holiday party to get myself psyched up for hanging around longer, for instance — that might have backfired. As it is, I feel like I've gotten to know an interesting person a little bit better, and I'm content with that.
2. I tend to really regret impulsive decisions I've made when wasted, but not impulsive decisions I've made after a glass or two of wine. A little booze can help loosen us up and relax enough to trust our instincts, but having too much in order to help yourself do something you're nervous about doing is never a great plan.
3. Taking risks with a considerate person is infinitely preferable to taking them with a jerk. How to tell if a person is considerate? I know; it's not easy. But your gut will probably give you a good indication. Also, if he treated you with respect and courtesy when you met, and if he responds to your e-mails, texts, etc., in a timely way, those are good signs. I find that the only risks that are painful for me are the ones in which a person just ignores a gesture I've made; as long as someone responds and explains — as a considerate person is likely to — it doesn't hurt so much, even if he doesn't do what I was hoping he would.
4. Use technological means of communication for making invitations and setting up dates; wait until you're in person to express affection. When you tell someone you think he's sexy or fascinating by e-mail or text, it can seem like a bigger deal than it would if you simply said — off-handedly and spontaneously, in person: "Wow, man, how cool are you?" Or, "Dude, you look hot in those jeans." Or whatever it is you feel compelled to say.