Hey everyone Shogo here heading back on a train from my friends wedding in Connecticut. Good time and it got me thinking about how people love to be challenging.

In dating, being challenging is great. It’s part of the picture when you’re just meeting someone new. You don’t want to be overly agreeable with this new person you hardly know, and you certainly don’t want to be a pushover and play it too safe.

Being a challenge is also fun. You get to enjoy the push-and-pull, you get a sense for each other’s sense of humor, and you build up anticipation and sexual tension right from the get-go.

But be careful when your challenges start backfiring. For a lot of you guys, I know this is happening. A guy who’s too challenging can easily end up repelling women when he’s out getting to know people, be at a bar, at Whole Foods, in line at the coffee shop, you name it. Act too cocky, and people will start shying away from you.

So how do you know when you’re being TOO challenging? It’s when you’re turning the moment into something that’s no longer fun. It’s when you’re going out, and you’re racking your brain about HOW you can be a challenge to this woman right now. If it seems like it’s just so much work to come up with all these challenging, funny lines, you’re going way over the top.

Playing Hard To Get

A very bold, risky woman may respond to that kind of behavior, but most people in everyday situations won’t. Most people respond to someone who’s friendly, who’s got a great smile, and who’s staying present in the moment interested in what’s going on around them. If your challenge is coming out of nowhere because it was something you thought so hard about to say, and not based on something going on in the moment, you’re done. You’re being fake, you’re overcompensating for your insecurities, and you’re going to get blown out.

A challenge demands a challenge back, and if the woman you’re talking to is not comfortable with your major attitude coming at her from out of the blue, she’s thinking, “What the hell is going on!? I was just fine before this guy came along, and now I’m not. I’m outta here because it’s going to take way too much effort to try and keep up with this clown right now.”

I was at Whole Foods with a client last weekend, and at the beginning of the day he came way over the top with all his challenges. We’re getting sandwiches, and he pulls a ticket. As we’re waiting in line chatting, we miss our number being called, and two women order ahead of us.

“HEEEEY,” my client says to the girls in a loud sarcastic voice, “We’re up! Unless you want to buy this ticket from us, eh? How much? $100?” Now he was smiling and trying to be funny and engaging, but it was way too much for the sandwich line at Whole Foods at noon. The girls basically got scared, looked at him really quickly and said, “Oh, sorry, you go ahead.” And that was that.

I told him he had the right idea, but he really had to tone it down. I told him to watch me as I sidled up next to one of them and said in a normal voice, “You know, you did cut in front of us but I’ll let you go this time,” with a smile and a wink. And we proceeded to have a great conversation about all sorts of stuff.

Luckily my client was a great guy to work with, just a great all-around guy, and he watched me and got the picture right away. The very next interaction he had, we saw two more cute girls outside Whole Foods in the pumpkin patch. He walks up, talks to the girls about pumpkin carving and how he’s never carved a pumpkin, and the next thing you know, boom, one of the girls is taking down his information in her iPhone. All because he cut out the fake challenging behavior that wasn’t really him to begin with.

So next time you’re out, ask yourself not only if you’re being funny. Also ask yourself whether you’re actually fun to be around. Watch the reactions of others around you when you challenge them… Do they laugh and go along with it, and give you a little bit of a fun challenge back? Or do they give you a strange look and take a couple steps back?

People like to have a little fun, people respond to a fun challenge, but if you come across too strong, you’re being fake and everyone in the room can smell it.