THE BLOG
04/18/2016 05:39 pm ET

Dry Wit and Sarcasm... Be Careful What You Wish For!

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I hear from clients and those who date my clients that they desire someone to match their dry, witty personality. This is a euphemism for I can dish it out. The dry wit can be construed positively, for sure. The man or woman with the dry wit has unbelievable observational powers. You can sit on a park bench with them, people watch, and they can dissect a passerby with pinpoint accuracy. They narrate the inner monologue of the rollerblader (no judgments), guy carrying the frisbee (again no judgments), and the thirty-three year old wearing his fraternity sweatshirt (now I'm judging a little).

Oh, but then she sets her dry wit on you. Can you handle it? For some, it's banter, slight ribbing and they can take it like a sport. For others, it's downright offensive. It crosses from dry wit to teasing. The late British author Anthony Powell described dry wit as follows: 'there is no greater sign of innate misery than a love of teasing.'

I have no idea whether I agree with Powell or not. I do know that before you pronounce to the greater dating world that you are looking for someone with a dry, witty personality, be careful that you are not just begging for someone to mercilessly make fun of you.

There are extremes. Perhaps the dry, witty personality at its best can be charming and has a built in governor. There are well-delineated lines she knows not to cross. She might make fun of you, or others, but she knows when it's below the belt. The witty, dry sense of humor at its best can be a form of intelligent, satirical playfulness.

At its worst, it's condescending, sanctimonious bullying and you start feeling terrible about what you asked for, or thought you wanted. Then there's you. Are you repelling people with what you perceive as dry wit?

Maybe you're the only one laughing. On the other hand, you really do not want to be boring. So it's a balance. Never easy, and with dating, as with wit, timing is everything. You might leave your arsenal of wit for a more advanced relationship.

So perhaps you start making fun of his skinny jeans on date three as opposed to date one. You poke fun of her loud popcorn smacking on date five as opposed to date two. The truth is, if you have the dry wit or you are searching for the dry wit, it's coming-out eventually. Perhaps the answer for the person who wants it, or has it, what's the proper amount to give? When? And where are the boundaries?

As always, I would love to hear your thoughts.

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