A friend of mine recently came to me for dating advice and he’s OK with me using him for the blog. LOL.

Here’s the thing. He’s known this girl since high school and lost touch with her until recently, when he bumped into her at some event. So he went out of his way to organize this charity event to invite her to come out so he can casually talk to her. Now, he wants to ask her out but doesn’t want to make it awkward since they haven’t spoken for so long. So he doesn’t know what to do. He’s not sure whether to ask her out to lunch or dinner.

And here was my advice to him. Yes, it will be awkward to suddenly ask someone out when you haven’t spoken to them in ages. You’ve got to keep it casual. Since he’s already tried offering to find her a job within his network of “peeps” and currently has her resume in his possession (it stinks), I’ve told him: “OK look, don’t jump the gun. Don’t ask her out to dinner because that’s too soon. You should ask her out to a casual lunch so you two can go over her resume together. You don’t want to re-do the whole thing for her, do ya?” He said, “Hell no.”

I said, “Alrighty then. Use this opportunity to sit down with her and talk. Ask her what it is she really wants to do so you have a better idea of what she’s looking for so you can gear her resume towards that direction. So that way, you’re keeping it down to earth, casual, friendly; she will appreciate you for helping her and will be totally smitten!” Then after a few more “casual meetings” he can slowly progress into asking her out to a real dinner date. That way, he can slowly buid a connection with her again and it wouldn’t seem so weird.

My friend is a nice guy, and he knows nice guys usually finish last. He said to me, “For the girls I don’t care about, I just ask them out like nothing. But the ones I care about..” I cut in, “…are the ones you get nervous over.” Yup, I’ve seen that happen. I’ve been in his shoes before so I know exactly how it feels. I told him, “Dude, why don’t you reverse-psychology it. Don’t get nervous over the ones you care about. Or even better, just simply don’t care about either one! The more you care, the harder it becomes. Besides, she’s not the last girl on the face of the planet.”

Well, I’ll just wait and see whether my advice to him works. I’m keeping my fingers crossed for you, man!