How to Date with a Sense of Humor

Couple Laughing TogetherEverything was going so well. The tuna was properly seared, the chardonnay crisp and dry, and you hadn’t once wondered if there was an exit out back for a quick escape.

But no sooner she thinks, “Hmmm, maybe I won’t be falling asleep to Wolf Blitzer tonight,” then it happens — you crack a joke only the boys would high-five you for and your date doesn’t know where to look for reassurance.

Pretty soon, you’re talking about having “a sexytime” with her, and your table is drawing the kind of looks normally associated with drunken frat boys on pub night. Dinner has turned into Evening at the Improv with your Uncle Ralph.

Guys, Listen up.

All those Borat impressions, Russell Peters one-liners, and SNL skit reenactments — fuhgeddaboutit.


“What girls mean by ‘sense of humor’ isn’t necessarily what guys’ first instinct is,” says Pete Johansson, a Vancouver comic.

Of all desirable qualities women mention in their profiles, sense of humor is one of the most common. But the phrase could mean anything, from knock-knock jokes to withering sarcasm to a T-shirt that’s supposed to look like a tux.

“Most guys think ‘joke-y’ when they hear that,” says Johansson, a touring comedian who regularly performs standup at clubs such as Punchlines and Yuk Yuk’s.

What women mean, he suggests, is a guy confident enough to make fun of the most potentially pompous subject of all: himself.

“The thing girls hate the most are guys who are self-centered and obnoxious,” he says. “And a sense of humor is another way of saying you’re not self-centered and obnoxious. You can’t have a sense of humor and be that way, because ultimately you have to laugh at yourself.”

Jen Grant, another comic, agrees. “There’s a big difference between laughing with someone and laughing at someone,” she says. Besides performing on stages and in TV shows, Grant has reeled off her riffs on free-range chickens and other subjects to soldiers in Israel and Egypt, and is taping her own TV special this fall. She is also the first female to make it into the finals of the Boston Comedy Competition.

“I’ve been on dates where I couldn’t believe the person was for real,” she says, recalling one such episode, when she found herself on a date at a karaoke bar. “He started singing loud Guns N’ Roses songs in my face. I wanted to burst out laughing. That was hilarious but he didn’t know he was being hilarious.”

All this bad date comedy in restaurants — whose fault is it anyway? After all, it’s women who are always advertising for a guy who is “witty,” “has a great sense of humor” or is “wickedly funny.” All guys really want is someone to laugh at their jokes. So can a dude really be blamed for boning up on Steven Wright one-liners before dinner?

Yes, says Grant. A sense of humor should be “an indication of good social skills, confidence, and intelligence,” not the ability to repeat lines from Seinfeld. Use that knock-knock joke at your own peril.

So What’s a Guy to Do?

Johansson has a few tips. For instance, comedians make great dates because they listen. “Most good comedy is listening,” he says. “You listen to the audience to make sure your next step is appropriate. And you do the same thing on a date. A lot of comics can listen to a girl talk and play off that,” he notes.

His other recommendation: don’t try too hard.


“You should never be trying to be funny,” he says. “You should be trying to be comfortable. Everyone, when they’re relaxed and are being themselves, knows the comfort zone of where you can jest. A little bit of honesty is the best kind of funny. If you’re trying to crack wise or lay down a joke, you’re coming across like the boss on The Office. It’s when you’re being disingenuous and trying to be something you’re not that the jokes come off as shrill and scare people.”

Of course, it’s a two-way street. But the funny thing is men don’t seem to put as high a premium on a sense of humor, at least according to a random sampling of online dating profiles.

“It takes a man with healthy self-esteem to be with a woman who’s funny,” says Grant. “A woman who’s funny is confident, assertive and intelligent. I like how I say that, being a comic myself. Did I mention modest and humble?”

She recalls what happened after a love interest caught her act. “I got a great response from the audience, and afterward he admitted he was really intimidated. He was already dating me though. ‘He was like, ‘Wow, you were really good, and I felt so small.’ I didn’t like that that created tension. Even that to me was a bit of an indication of how men feel. But he was confident even enough to admit that.”

Johansson disagrees. “I found the girl I’m going to marry, and the thing that absolutely was the linchpin for me was her sense of humor. Knowing we laugh at all the same things is the single most important thing.

“I’ve dated girls who didn’t have my sense of humor,” he continues, “and it’s hell. You’re walking on eggshells all the time, thinking, ‘This is funny but I’d better not say it.’ When you have someone with the same sense of humor there’s nothing freer. I think it’s very important to guys. That, and a nice ass.”

Marilyn Kane, an aspiring comic, says she’s been on dates where the guy just didn’t get it.

“I’ll start complaining, and he starts problem-solving,” she says. “And I’m like, ‘Dude, this is my comedy routine. I’m not asking for your help.’”

But perhaps the most important ingredient with humor, as with love, is the timing.

“I’ve dated a couple of comics,” says Grant, “and I’ve noticed guy comics, when it should be a romantic or nice moment, will see an option for a joke that’s hugely inappropriate. But they will always take that before my interests. And it’s hard when it’s a funny joke because I respect that. I’m like, ‘Good fuckin’ joke. But I hate you right now.’”

Lavalife About Lavalife is one of the original players in the online dating game. Committed to helping its members find fun dates and relationships, Lavalife is a prime source for online dating, dating and relationship advice.

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