How to tease a woman respectfully

I’ve been wary of writing about how to tease women for a long time because there are a lot of sleazy ways to do it. Too many dating advice gurus and pickup artists will tell you to “neg” her by giving her a backhanded compliment so that you lower her self-esteem until she decides to go out with you.

Ugh! It grinds my gears that this type of advice even exists.

Ultimately, I decided to write about teasing because it is a valid form of flirting and there is a way to tease women respectfully. And I think it’s about time that someone wrote about how to tease women in a way that is both non-sleazy and respectful.

The most important thing to remember when it comes to teasing is to do it respectfully.

Respectful teasing is: playfully insulting her without intending to hurt her feelings

Respectful teasing is NOT: insulting her with the intention of actually hurting her feelings

Only jerks tease women by belittling her and trying to undermine her self-confidence. Instead, you want to tease her respectfully. Always be conscious of her feelings. A respectful tease involves saying something slightly edgy or irreverent that will catch her off guard, but without making her feel uncomfortable or offended.

The way I like to think about it is that respectful teasing is similar to the way you might “trash-talk” your friends when you’re being competitive towards them. My friends and I are typically fairly polite when we interact with each other. However, every once in a while we all get together to play Wii Sports or Uno and when we do—that’s when the kid gloves come off. We’ll freely hurl insults at each other and call each other words that are spelled similar to “pansy” or that mean “homosexual person”.

It’s all in good fun, though. We never intend to actually hurt each other’s feelings. Quite the opposite. We would never behave this way towards someone unless we weren’t friends with them first. By throwing these types of insults at each other, we’re really showing that we’re cool with one another. Thus, by teasing a woman respectfully, you’re playfully signaling to her “Hey, I think you’re a cool person.”

Cool, huh?

Teasing can be separated into “light” teases and “daring” teases. The type of tease that is appropriate depends on several factors. If she has a more conservative attitude, or if she’s just a friend, or if you’re in a place where proper manners are expected then you may only be able to do a “light” tease. On the other hand, if you’re romantically involved with her or you’re in a setting with a lot of alcohol involved such as a bar or club then you may be able to get away with a more “daring” tease.

How to do a “light” tease

Once upon a time, I was waiting in line at Starbucks and a woman was coming in behind me to get in line as well. As she gets in behind me, she stumbles over her feet, takes a couple of clumsy steps forward, and almost falls over before finally regaining her balance.

I watch her make a spectacle of herself. She regains her balance and looks at me. I don’t say anything but I give her a confused look like…

She looks up at me sheepishly and says, “I tripped. It happens.”

I wait a couple of seconds, sigh, and shake my head. Finally, I respond:

“Really? Does it happen to everyone? Or just you?”

Since I didn’t even know her at all and we were in a coffee shop, I used a light tease. I didn’t say anything offensive or sexual, but I still poked fun at the fact that she almost tripped and fell over. Also, what I said was pretty darned clever if I do say so myself!

Recently, I want to a gala with a female friend of mine. She started to drink and asked me to stop her before she drank too much. After a few drinks, she decided that she had enough and I noticed that she had a little trouble keeping her balance throughout the night.

“Are you drunk?” I asked her.

“No, just a little tipsy” she responded. “It’s hard to walk in high heels.”

“I think you’re drunk” I insisted.

We started interacting with another guest at the gala. After breaking the ice with the usual introductions, the three of us got to talking a little bit. Suddenly, I blurted out to the group,

“Please excuse my friend here. She’s a little drunk.”

She turns towards me and replies, “I am not drunk!”

I shake my head while rolling my eyes and let out a slow sigh. Then I respond, “That’s exactly what a drunk person would say.”

The guest we were talking to started laughing and agreed with me. For a moment, I think I was able to convince my female friend that she actually was drunk (even though I knew full well that she wasn’t).

This is an example of a slightly more “daring” tease than the story from the coffee shop. It’s still a “light” tease because it doesn’t involve anything offensive or sexual, but I figured that I could be a little bit more daring because she’s my friend and I knew she wouldn’t hold it against me.

Finally, I was recently the victim of a “light” tease myself. A few days ago, I ran into one of my close female friends near the building that I work in. Later, I heard from my circle of friends that she had been telling everyone I looked “dumb cute” when she saw me. I texted her about it and she replied…

…that I looked ”no cute, only dumb”.

Ouch!

We’re close friends, so she knows that she can get away with insulting me outright and I won’t get upset at her. And honestly, I can’t help but admire how clever her tease was.

How to do a “daring” tease

The last few examples were “light” teases, which are appropriate in a variety of social situations. On the other hand, “daring” teases should be used with caution. The only time I’ll use a “daring” tease is if I’m already romantically involved with her or if I know that she’s romantically interested in me. “Daring” teases can sometimes be appropriate in bars or clubs where there’s a lot of drinking involved. Also, if she starts using a “daring” tease on you first then it’s safe to assume that you can use a “daring” tease on her as well without offending her.

A few years ago, I was going out with a woman and we had gone on a few dates before but hadn’t done anything physical up to that point yet. We hadn’t even kissed yet. That Friday night after I get home from work, I take a shower and then I call her up to ask her out on our next date.

She answers her phone, “Hey Steve! What’s up? How are you doing?”

I respond, “Not much. I just got out of my shower.” (Notice that I said I just got out of *my* shower.)

She says, “Oh yeah! Me too.”

Whoops! I knew exactly what she meant, but what she said was something completely different and I wasn’t about to let that go without embarrassing her about it. I replied,

“You just got out of my shower? Were you showering with me? How come I didn’t see you?”

This type of “daring” tease pushes the boundaries sexually. We were romantically involved with each other but we hadn’t done anything physical yet, so when she made her little slip-of-the-tongue I took the opportunity to innocently make the conversation more sexual than anything we had done before.

Several years ago when I was still in college, I was working at my first internship and I had a crush on one of the other interns there. There was always some tension between the two of us and I knew that she liked me too. One day, we were on our lunch break and the two of us head out to a restaurant to get something to eat. We sit across from each other at a table and we ended up talking about tattoos. I ask her if she has any tattoos and she tells me that she has one in the shape of a star.

I pause and think for a second. At this point, I’ve worked with her for almost a year and I’ve never seen this tattoo anywhere before. It’s not on her arms, face, neck, or legs. I realize that her tattoo is probably in a very personal place. Here’s an opportunity for me to do a “daring” tease.

I lean in across the table towards her so that my face is only a few inches away from hers. Looking straight into her eyes, I ask her,

“Where is your tattoo? Can I…see it?”

She suddenly looks sheepish. My instincts were correct. Her tattoo was in a private place on her body, and now I’ve got her thinking about her own sexual areas. The best part was that I’ve maintained plausible deniability. Was I really trying to make the conversation more risqué? Or was I just asking an innocent question?

Teasing with care

When it comes to teasing, you always want to do it respectfully. Always be mindful of her feelings when doing a tease. This means taking into consideration: the environment, her attitudes, how close you are to her romantically, etc.

“Light” teases are generally okay to use in a variety of social situations. Keep in mind that “light” teases are what Dr. Hall considers a “playful” method of flirting—meaning that it doesn’t imply any romantic or sexual intent. It’s merely a fun way to break the ice. As we’ve seen above, I use “light” teases on my friends all the time and it’s not inappropriate at all.

“Daring” teases push the boundaries more than “light” teases. This type of tease typically implies sexual intent—but not romantic intent. I’m personally not a fan of casual sex and I’d much rather be intimate with someone that I really care about. Thus, I won’t try to do a “daring” tease unless I like her or I’m already romantically involved with her.

Finally, always be your best authentic self when interacting with her. There are a lot of dating gurus who will tell you that you absolutely, positively need to tease her when you talk to her or else she will see you as a friend and nothing more. There’s a few reasons why they do this, but it’s not the end-all-be-all that they make it out to be.

Don’t tease her in a way that makes you feel sleazy or uncomfortable. The most important thing to remember is that she should be comfortable with the way you tease her and that you should also be comfortable with the way you tease her.

That’s how you tease a woman respectfully.

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