Yesterday, after preparing our post about how to be funny, my dear friend Teddy Wayne and I ended up discussing self-deprecation not just as a tool for humor but — when it's a compulsive reaction — as something of a personality flaw, particularly in the dating realm, particularly early on in a dalliance.

"I feel like I point out my flaws all the time — in part because I want to signal my self-awareness. Or else I want to make it clear that I'm not clueless about some appearance drawback on a certain day. Like, a lot of times I say, 'My hair is just a mess today — please try not to look at it too closely.'"

Teddy's response: "Which surely makes people look at it too closely."

"I know, I know."

"You actually did something like that the first time we hung out."

"I did?"

"After that party where we were introduced, we met for drinks."

"At that Bar 115 place — that time?"

"Yeah. You called me shortly before so we could pin down a time and you said, 'I'm just warning you, I've been running around all day so I look really gross.'"

"Ah, I have such a way with words. And did that make you say to yourself, 'Hmm, let me check her out and see if she does look gross?'"

"I'm sure it didn't help."

(Thanks, Teddy.)

But the very night before, I'd been the intended audience for a self-deprecating statement — and I saw firsthand how it can be kind of unattractive.

I was on the phone with a friend of mine whom I hadn't spoken to in a while, and at a certain point he said, "Well, I'm just rambling now." I hadn't thought he was talking in circles at all, but after he called my attention to the possibility that he might be, I found myself on the lookout for a ramble as the conversation continued. His comment had become an invitation to judge him and scrutinize him.

What's more, when it was my turn to talk, I started to feel neurotic about my own speech; if he was so sensitive to the possibility of his rambling (when he hadn't been), was he going to be very judgmental about it if I rambled?

My convo with Teddy also reminded me of an incident in college: A male friend of mine was pretty interested in a certain girl ... until one summer day when a bunch of us went for a swim at a pleasant little mini-waterfall very imaginatively named "The Rocks." The girl-of-interest — who had a very attractive athletic bod — was wearing shorts and a T-shirt. When someone asked her why she wasn't wearing a suit, she said, "I'm just not the type who will ever look good in a bathing suit." My friend quickly lost interest — and when I later asked him why, he said that just thinking about how she never would look good in a bikini was a huge turnoff.

So, three reasons to stay away from self-deprecation when you're first getting to know a new dude (and even a new friend):

1. Self-deprecation is an invitation — nearly a demand — to pay attention to imperfections, flaws, or peccadilloes that someone may not have ever noticed (or paid much attention to) before.

2. It doesn't make you seem self-aware so much as insecure.

3. It can make the person you're speaking to wonder if you will turn your negativity or hyper-scrutiny on to him or her.

That's all for now. Let me know what you think!

What Do You Think?