(Partially excerpted from God is a Woman: Dating Disasters.)

Flirting is key to successful dating and picking up women. Some guys are naturals, some aren’t. How can a guy who’s not good at flirting get good?

I used to suck at flirting. Now, I like to spend almost the entire first date flirting. I find it leads to more second dates. In fact, the best two relationships I’ve had started with excessive flirting.

How did I get good? I watched other guys flirt. I said things that popped into my head that I thought were too risqué to say. I pushed the envelope. These are the ways to get good at flirting.

Guys can practice flirting with other guys. What?! Relax, pay attention. When I’m out with other guys, we rip on each other all the time; it’s how guys bond. This ripping is not all that different from flirting. Consider a tennis match I recently played against a friend. He hit a ball into the net softly several times in a row. I ribbed him, “Hey, if you’re gonna play like that, at least trade those shorts in for a skirt.”

After he had a few miss hits—gifts to me on points he otherwise would have won—I ribbed him again, “Slut, I’ll drop you off on your corner after the match.”

One day I was playing hockey when the opposing team scored a soft goal through our goalie’s legs. Our best defenseman turned to the goalie and said, “Close your legs, you whore.”

This is not that different from the day I approached a woman who played on four different volleyball teams and asked, “You’re just a volleyball slut, aren’t you?”
Practice with the guys then tweak it a little for the ladies; good flirting will be the result.

Here are some real-life examples of me flirting that worked wonderfully (with women not guys, just to be clear):

1 - To two women holding a balloon with drawings of people in different sexual positions on it: (I approached them from behind and pointed to positions over their shoulders.) “Done that, done that, done that—ooh, that looks good—done that. So, which are your favorites? You can just point without naming them, so it’s less embarrassing.” They looked at me and laughed. I quickly followed-up with, “Hey, I’m a gentleman.” (Always remain chivalrous in your flirting.)

2 - To a woman wearing a low-cut top three sizes too small: “Wow. Okay, that is way too distracting. You should hang a little baggie of cookies from between them… or did somebody already grab that? I will sacrifice and settle for what’s left-over.”

3 - To a woman wearing what would be described better as shoe laces than a bikini: “Excuse me, I have something between my teeth. Can I borrow that string? The one that seems to be holding everything together?”

4 - To women who play a lot of volleyball for different teams, subbing: “So you’re just some kind of volleyball whore, aren’t you?”

5 - To a coed in my Oceanography class wearing a short skirt, with silky legs that ran up to her neck: “All the seats are taken. Do you mind if I sit under your desk? Please?”

6 - To a woman at a bar in tight jeans with a great ass: “People tell me I’m an ass. Do you mind if I snap a picture of yours for my facebook photo?”

“For your facebook page?”

“I figure if you’re going to be an ass, you might as well be a perfect ass.”

I could go on and on but you get the idea. Women screw guys who flirt; not guys who don’t. Of course, feel free to share some of your successful flirt lines, too.


Be sure to pick up a copy of Ian’s bestselling book (not only because it’s full of good stuff, but also because I’m not paying him), God is a Woman: Dating Disasters.

And find excerpts and Ian's other columns here.