Teasing Is My Love Language

But when does it cross into disrespect?

I tease everyone a little, but I double down when I have a crush on someone or I’m flirting with them.

I never gave it a second thought before. I spent years being fully monogamous and mostly housebound. These days, though, I have a lot more interactions online. I’m also kind of lightly dating — sort of on the scene, sort of not. And after 15 years of playfully teasing my husband, I find myself having to navigate the dynamics of teasing with new people.

One of the challenging things about flirting with people after spending so many years out of the game is that I’m not always sure where the line is. How can I tease someone without going too far?

I’m also trying to work out the difference between teasing and just begin a jerk because I’m on the lookout for that kind of behavior in others. I don’t want to mistake some bullshit pickup artist tactic like negging or being cocky-funny for well-intentioned banter.

But trying to figure things out often leaves me second-guessing myself.

A little while ago, I was texting a guy I liked. He introduced himself to me, told me he liked my writing, and we seemed to be hitting it off. At the end of our first conversation, he said “I really hope you’re enjoying your Tuesday.” Only, we were Wednesday. He got the day wrong.

I felt an overwhelming urge to tease him about it, but I hesitated for a long time.

I worried that acting too familiar, too fast might hit a nerve with him. Maybe making fun of him for his mistake would embarrass him and I would fuck things up before we even got to know each other.

I second-guessed myself so hard that I even started looking at time zones across the world — what if it was Tuesday somewhere?

It wasn’t, and my window to tease him about it was closing.

At the last minute, I decided to just go for it. If he’s going to like me, he should like the real me. And the real me is playful and teases — a lot.

I was gentle with him. I wrote, “I hope it’s not too early in our friendship to make fun of you, because it’s Wednesday.”

I was relieved when he wrote back. “No, it’s not too early at all, especially since you’re a day ahead of me.”

Good. Now we were really getting somewhere.

My attempts at teasing don’t always go so well, though.

A few months ago, I was exchanging emails with a chef. His emails were fun, and I could see myself getting to like him.

But then I tried teasing him.

I jokingly ended one of my emails with “I hope you have a good day at work and no one gets food poisoning.”

(Okay, not my best material, I admit.)

That sentence earned me a paragraphs-long reply. Actually, “reply” is the wrong word. It was more of a tirade. He went on and on about how his restaurant is very high-end, that it’s won awards, and that “it’s not some fucking McDonald’s.” Then, he told me to never talk about that sort of thing with him again.

Harsh.

This and another similar incident showed me that I wouldn’t be able to have comfortable conversations with this guy. I would always be on edge, always worried about what I said to him. So I called it. I stopped talking to him because it really couldn’t go anywhere.

But it just left me more confused. Where’s the line? When is teasing fine and when does it go too far? With the chef, it was clear to me that his reaction was disproportionate. But I still don’t want to push the wrong buttons or upset anyone.

Why I Love Teasing

One way out of this problem is to just stop teasing people. I could just be serious with them, joke about other things and other people but leave them and their restaurants alone.

But where’s the fun in that?

And teasing isn’t just me shooting the shit pointlessly. There are a lot of good things that come from teasing, and I wouldn’t want to miss out on those.

For one thing, it’s a quick way to make sure someone’s sense of humor matches mine. That’s even a good litmus test for how compatible we are in general. If there’s some overlap in the way we joke, it means we’ll be able to laugh together and have good, easy, flowing conversation.

Teasing is also a shortcut to building intimacy. It’s a way to signal you like someone without actually having to say that you like them. And when people take your teasing playfully, they reveal themselves to you more readily. It disarms them and gives them an opportunity to show who they really are, not just the persona they’re trying to project.

It’s also a good way to keep conversation going. When you tease someone, they can tease you back. They can laugh about it and then tell you the story behind the thing you’re teasing them about. Handled well, it escalates the conversation instead of letting it die down.

I also like the way that teasing can be a challenge. No matter how much you like someone, when you tease them you’re fronting like you’re not completely impressed by them. It invites them to do or say something to change your mind.

But the best thing about teasing is that it shows that you’ve been paying attention to the person you’re teasing. It’s often an opportunity for a call-back or to point out something you noticed about them.

And besides, flirting can be fucking awkward. Unless you’re moments away from fucking, keeping it serious will just ratchet up the tension and the pressure. Teasing keeps things light and fun so you can just enjoy yourself instead of having to confront all the nervousness you keep trying to shove back down into your gut.

How to Tease Without Being a Jerk

I’m a worrier. I don’t know that I’ll ever be able to approach someone new without asking myself whether I’m saying something wrong.

So, here’s the approach I take. As long as I’m doing this, I’ll know I’m not just being mean. And as long as someone else is taking it with me, I’m more likely to think they’re being playful and not just an asshole.

I start off by playing things safe. Before I tease someone for the first time, I make sure that what I’m about to say to them is 99% likely to not offend them.

I choose something light, something that shouldn’t really bother anyone. The food poisoning thing, that was a little advanced, but we had exchanged teasing banter for a while. He also kept describing himself as sarcastic and wasn’t shy at all about making fun of me, so it felt like a green light. But the “Dude, it’s Wednesday” line was a lot more innocent and a safe way to tease someone for the first time.

If I can, I’ll start by teasing them about something they’ve already been self-deprecating about. That’s about the safest ground you can find (though still not guaranteed not to upset someone).

Some stuff is off-limits unless you’re in really deep with someone (sorry, Mr. Austin). You shouldn’t tease someone about something that isn’t in their control, like their bodies. Always stick to decisions they’ve made, like their outfits. So, “You’re surprisingly confident for a guy with a chin like that” is not cool at all, but “That’s funny coming from a guy wearing suspenders” is still on the table.

Wednesday Guy, for example, took the bold step of quoting rap lyrics to me and then I took every opportunity I could to make fun of his taste in hip hop. I even went full-blown troll and sent him a link to Wham!’s Wham Rap! and told him it’s the only rap song I love.

I stuck to something personal but intentional. And you know what? It worked. Even though I spent the evening poking fun at him, he still had phone sex with me. (Though, granted, not on that night…)

Teasing also doesn’t pile on the insults. It’s a bit of gentle mocking, but it’s not negging. It’s not poking fun at someone and then saying some low-key mean shit to them.

And it’s contextual. When you’re teasing someone and not just being a jerk, you’re giving them other signs that you like them. You should be giving plenty of evidence about how you really feel so they’re less likely to misread your intentions.

But for me, the biggest sign that someone is acting like a jerk and not just teasing me is the way it makes me feel.

Playful teasing makes me feel a little flustered. It makes me giddy. It sometimes makes me a bit shy but it won’t make me feel silenced or dismissed. It makes me laugh and puts me in a good mood. And when someone is teasing me, it shows me they’re making an effort to get to know me, which makes me feel special.

And if teasing doesn’t make you feel special, then the person doing it is either being an ass or your senses of humor are just really incompatible. Either way, it’s probably a good idea not to go on a second date with them.

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