So what is his advice to an audience member who wants to know: How much of yourself do you give away to your date?
Will stresses the "three-date rule." "But always keep in mind that a rule is not a hundred percent," he says. "A rule is an accepted principle that will work most of the time. So you can get in the moment, but you can always adjust it and throw it out."
Date No. 1
The "first-date" rule is: Illuminate the best parts of yourself. "It's not about hiding anything; it's not about deceiving," Will says. "It's: Illuminate the things that you like most about yourself and that people like generally most about yourself. You don't want to walk in and say 'Come here, come see these leaky pipes!'"
Will says the first date should essentially focus on communication. Effective communication should happen naturally, so that you don't have to be cognizant of how much you're talking and how much your date is talking and make sure that you're both talking an equal amount of time. And remember, silence is not always a bad thing, he says.
Date No. 2
Will says the motto for the second date is: Exchange coupled with range. He explains, "So the idea of exchange is that there's something that you want to present as an offer of who you are. And there will be something that is received back. It could be a poem that your grandmother wrote—you're actually sharing some aspect of yourself." Most often, when you present your date with something about yourself, they will also open up. "That is an exchange and an offer," Will says.
Coupled with "exchange" should be "range," Will says. You want to show your date the different sides of yourself. "You want to be able to quote [rapper] Kanye West and [German philosopher Friedrich] Nietzsche," Will says. "You know what I mean?"
Date No. 3
The third date is about "keeping it real." "After you've had a great first date, you've had a great second date—you don't want to waste your time dating," Will says. "You don't want to have five months with somebody, and…you find out you're not vibing after five months ."
That is why by the third date, Will says, it's time to show your date your habits and quirks. "You let a little more of that [to] be seen because you don't want to hide that. It's like that is the essence of who you are. So, you want to know in 10 or 12 days that she can't live with it so you can move on." Besides, Will says, your habits and quirks aren't things you can hide. "You can't hide that cabbage gives you gas. You know what I mean?"
The Final Word
All of these concepts have to be connected to the places you take your date, Will says. "It's not just what you're thinking and saying," he says.
"For example, in illuminating the best part of yourself—if you're a great bowler, you want the first date to be in a bowling alley so you'll be confident and strong and you know you'll roll a 237," Will says. "You know it's a place you're strong. If you've never had sushi before, your first date shouldn't be in a sushi restaurant. You want in a place where people know you, you're strong, all of that. So you want to incorporate that idea into the whole evening."