How to "Help" a Guy Ask for Your Number

In the third and final part of my interview with the country's leading flirtation expert, Neil Strauss, we talk about the best flirtatious questions, how to effectively tease someone and how to help a guy along if he's having trouble ...

I hope you guys have been digging this week's tips from Neil Strauss, author of the best-selling pickup manual The Game. (I know I'm pretty excited to give this stuff a shot!) Here's the final — and perhaps the best — of my Neil posts. This one includes advice on the best flirtatious questions, how to effectively tease someone — and how to help a guy along if he's having trouble figuring out it's time to ask for your number!

ME: All right, so, once you've got down small talk and the physicality of flirting... It's conversation time! What's the best way to converse flirtatiously? How do you actually engage someone and get him to start chatting?

HIM: Pick a conversation starter, something fun that you want to discuss that will help you engage a little more with a guy. Maybe it's some article from a women's magazine that offers some kind of advice and you want to know if he agrees with it or not. Or maybe it's: "It's my cousin's birthday and I want to buy him a CD — but his taste hasn't evolved since the '80s. Any suggestions?" Or maybe your friend just got a three-legged cat and you need a name for it.

ME: Right! Or just a regular old cat. Or — I think people always like to answer this one — you're thinking of starting a band and you don't know what to call it.

HIM: Anything like that. And up front, you should immediately mention that you have some kind of time constraint, whether or not you do. Within the first sixty seconds of talking to someone, say, "I can only stay for a second, because I'm late for an appointment." Or late to hang out with friends or whatever.

ME: Does that reassure the person the conversation won't last forever?

HIM: Right. Although if things are moving along, you're hitting it off, go with it. The key is not to force it. If you sense things are dying down, it's time to move on.

ME: If he hasn't asked you for your number by then, is it okay for you to ask for his?

HIM: I think it works better if you can let the guy feel like it's his decision. Let him make the first step toward escalating things. Although if he's just totally clueless — or maybe scared of rejection...

ME: Could you then prod him along by saying, "Well, I better go, but we should hang out sometime?"

HIM: Yes, or even better, something more specific to what you've just been talking about. Like "Yeah, we should go to that new sushi place sometime."

ME: Or go see that new movie, or something.

HIM: Right. Or you could say, "Well, my friend is talking about having a party, we'd love to invite you..." And if he just doesn't get the hint, even after that, to ask you for your number, maybe he's kind of lame and you don't really want to be with him anyway.

ME: In The Game, one of your pieces of advice is for men to "neg" women they're flirting with slightly — to say something slightly negative as a way of drawing someone in, or causing them to want to win your approval. Does "negging" work for women when they're hitting on me?

HIM: I think a lot of people don't really understand the neg. The trick, when you're flirting, is figuring how to keep a balance between being engaging enough to retain someone's attention and not seeming overly available. So you tease a person a little. For a woman, it would be something like calling a guy on his shit — saying something like, "Oh sure you do ..."

ME: Like, "Oh sure you run five miles every day" or "Sure you make amazing eggplant parm" — something like that?

HIM: Right. The point is not to insult a guy but just to make him a little unsure of where he stands. Make him wonder: Is she serious about that? Or is she just making fun of me a little because she likes me?

ME: That kind of push-and-pull does make it more fun. Another thing: What kind of mind-set do you think a woman needs to flirt well? Like, should you go out thinking, "Nobody ever talks to anyone else on the subway, and I'll make somebody's day if I do that." Or "He's just standing in line at the coffee shop — it'll be a total bonus for him if I give him a little flirt with that cup of joe."

HIM: That sounds a little needy to me — like you're wanting a certain reaction. Don't worry about how guys will respond to you. If it seems like you're trying too hard, whatever you're doing will come across as desperate. Be more centered. Think: "I'm fun. I'm cool. I radiate charisma, I am free to do whatever the hell I want." It's all about feeling really good about yourself. The most important thing to remember while you're doing all this flirting is to make it fun for yourself — because then it will be fun for the other person.

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All right, guys, so there's the brass tacks from the nation's top flirtation expert! Do I have a minor crush on him? Absolutely! Have you tried out his advice? Keep me posted on how it's working out for you.