Dating Tips: How To Be Flirty And Witty At The Same Time

It’s the ultimate conundrum: play dumb while flirting to get the guy or voice your opinions, revealing the strong woman you are, and risk losing the guy. Here’s how to do both!

The accepted wisdom seems to be that women should agree with men if they’re flirting with them. For some reason, many people seem to think this is what men like.

For example, they tell you to compliment and speak highly of everything the man does, or ask questions about whatever seems to excite him, like motorcycles or hiking, even if the topic doesn’t interest you at all.

Now that is one way to go, and for some it might seem to work, but it certainly isn’t the only way. What’s more, it has several significant drawbacks:

  • It kind of spits on three generations of women’s attempts to be treated as equals with opinions that matter just as much.
  • If you’re not like that, and you have your own opinions, you’ll either have to suppress them for the entire time you’re together or get ready for some fireworks down the road.
  • It will waste one of the best opportunities you’ll have to discover if he’s a self-confident man or a fragile little boy.

I really can’t tell you which of those is worse for me! I’m quite disagreeable. I like my opinions, and I most certainly am not going to swallow my tongue just because he can’t handle it.

So I’ve started thinking outside the box, and taught myself how to flirt and debate at the same time.


It is important that you find the debate/flirting sweet spot on several fronts. These are:

  • You don’t want to be so agreeable you’re boring, but not so disagreeable that you fail to connect.
  • You don’t want to be so weak in your opinions that he’ll walk all over you, but neither do you want to bulldoze what he’s trying to say.
  • You also don’t want to be a cold fish so that he doesn’t know you’re interested, but also not so forward that he thinks you’re easy.

Instead, you need to find a middle way, where the porridge is juuuuust right. Here you challenge, but don’t insult. Your voice your opinions, but don’t dismiss his.

You show you’re interested without letting him think it’s a done deal.

Flirtation is playful

More importantly, you want to be playful in how you engage him. There is something joyful and childish in the best kind of flirting, as you laugh, tease and you get mock offended, all the time using these moments to physically signal that you’re interested even as he does the same.

Maybe that’s why couples regress to a more child-like state, showing unbridled joy, using baby speak and sometimes making noises that you wouldn’t expect from adults under normal circumstances. Or, maybe these two things are completely unrelated.

Whatever the case may be, if you’re trying to flirt while debating, then you have to introduce an element of playfulness. For example:

  • If he says he’s fanatical in the gym, you could ask him if his body or his girl comes first.
  • If he talks about wanting to be a musician, teasingly ask him if he still lives with his parents or if he gets his girlfriends to support him.
  • If he talks about always wanting to go hiking and you’re not into that kind of thing, ask him why he likes to wrestle bears.

The trick is to challenge him while leaving him with a way out, so that if he has a little bit of spirit in him, he can shoot it back your way. That way, you can get some banter going and bring your date to an entirely new level.

And yes, some men might not be able to take it, but as most of us want to date men and not boys, that’s not actually a bad thing. After all, this way you’ll know early and can move on to more promising prospects.

It’s a back and forth

Of course, don’t apply these rules blindly. It all depends on the guy you’re sitting opposite. Some men don’t have a sense of humor, but might still be great guys.

Some men might just need a little longer to get used to the idea. Take your cues from him (just as he is hopefully taking his cues from you). That way you’re not moving too fast or too slow.

Mirroring, which, in case you’re not familiar with it, is the imitation of the actions of another person that you like, doesn’t need to happen just on the physical level, but can also happen verbally. In fact, people who like each other start speaking at the same speed and same tone!

They start making the same kind of jokes and teasing each other in the same way. You know you’re onto a winning formula if that happens.

What’s more, you’ll know that you’re on equal footing, which is so much more interesting than having to sit there and pretend to look interested as he talks about his work. So disagree, and your dates might just become a lot more agreeable.

Author: Tina Murphy


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