1. Wait. Let the guy get to know you--appreciate you--before telling him.
2. Tell him right away. Give the guy the opportunity to run.
I've tried both options. I'll let you decide which turned out the best.
Option One, Wait: This is the #1 most recommended method for handling your virginity (Yeah, I know, that just sounded like some infomercial for wrinkle cream or acne wash). The general school of thought is that the guy will get to know you, appreciate you, and be more accepting, perhaps even try to stick it out. There is one slight hiccup, however: The Third Date. The third date is commonly known as "the sex date." I had been dating Bicker Dicker for about a month at this point, but, because of our hectic schedules, we had only been out on two dates (the rest of the time we were on the phone).
Third Date, Valentine's Day: After an elegant dinner, we hopped in his car and headed down the highway. It hadn't crossed my mind that this was date number three until he interrupted one of my favorite songs to play a "special" track he picked out especially for me. Okay, cute, right? The fact that his hands were shaking while he found the song should have clued me in. Damn. It was a sex song. Granted, it wasn't Bump 'N Grind, but it was distinctly sex-driven. I sat there, fairly calm, and waited for him to ask me back to his place. It never happened.
Turns out, he played the song hoping I would ask to go back to his place. Seriously. Beg for sex? Um, no. When I didn't, he put on the pout of the century, dropped me off in the middle of my icy driveway, and roared off down the road. So, there I was in brand new heels, trying to get to my door without busting my butt on the ice. Though he called three days later, acting like the attentive boyfriend (it was kinda creepy, really), I couldn't get over the fact that he left me in the icy driveway, at night, in heels.
Option Two, Tell Him: Yeah, I did exactly this before my first date with a certain man. I expected him to run. He didn't. He stalked. For over a year. Yeah.
Neither option worked out so well for me. I suppose the best thing to do is listen to your gut--if your gut says, tell him, then tell him; if you aren't comfortable telling him, wait. If he's the right one, everything will just fall into place...hopefully.