Getting old never dated

I find that it's a lot like going for a job interview. Take a balanced approach. You want to be confident, not cocky. Funny, but not a goofball. Honest, but not overly self-revealing. Be well-rounded. Have interests, not obsessions. ("I enjoy model railroads," not "I converted my mother's basement into a scale model of the state of Pennsylvania.")

Relax. Seeing someone, like a job interview that's going well, should feel more like an organic conversation and less like a police interrogation. Emphasize your positives and downplay the negatives. Do not come off like you have an axe to grind; do not bad mouth old workplaces/old dates, even if you feel it's true, and they all deserve it. ("The managers at my last job were all crooks"/"She turned out to be a cheater and a liar, like all the women I've ever met.")

Don't come off as too desperate. You have something to offer, otherwise you wouldn't have gotten this far. Desperation translates into anxiety and fear. No: "If I don't get this job/get her to be my girlfriend, I'm going to die." Yes: "I have a lot to offer this workplace/person."

Be friendly and polite. Asking thoughtful questions demonstrates genuine interest. ("I looked at the company's Web site and noticed a push into cloud computing. Can you tell me more about the direction the company will be going?" "What was the last movie you saw? Really, what do you think of Guillermo del Toro's other films?")

Remember to have fun. Just like you wouldn't ask what kind of retirement party the company will throw you during the first interview, don't obsess over whether this person is wife material. And if you get turned down or don't get to the second meeting, move on. Some relationship or workplace experts may recommend asking the person why you didn't get the job/go out again, but I don't think it's productive. In both cases, I'm not sure you'll get an honest answer.
 
I'm a female so my advice might not work as well for a guy. But when I am interested in a guy, I invite him to some sort of event where there will be a lot of people. If it is a guy from work, then I get a bunch of people together and invite him along. Otherwise, I might throw an informal party and invite a few people, including him.

I try to play it off not like I am hitting on him but that I'd like him to get in on the fun. Of course there is the chance that he'll bring a date along, but this technique usually works for me.
 
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