What? Men don't want a funny date? Female jokesters say it’s tough to find a boyfriend

We met at a New Year’s Eve party. She was blond, I was nervous. So I slipped in a joke, something stupid from third grade, but it did the trick. A first date was granted, followed by three more. I found her affable, warm, possessed of most excellent hugging skills.

But the three most peculiar seconds of my past year occurred shortly after my relationship with this woman – who shall hereafter be referred to as “Woman” – became official.

We drove one night southbound on Lake Shore Drive. I, man I was, attempted to retort something she said with a humorous response, hoping to elicit laughs.

Woman laughed. All was proceeding as planned. What happened next threw me for a loop.

She answered with a funnier line. At least twice as funny as the funny response I had made moments before. The exact line of conversation and punch line escapes me, but this is irrelevant. What mattered was the manner in which I reacted.

The normal physiological response would be to laugh, but here, I did not. For 3 seconds, I froze in confusion. The thought entered, God forbid, that this girl might be funnier than me.

Look. I am no chauvinist. The premise that a woman could not, should not be funnier than a man was absurd and offensive. Still, at the root of my reaction was a question I had never considered: Are men intimidated by funny women?

I turned to a source with scores of funny women – Chicago’s improv community – to find the answer. While it would be reckless to make a blanket statement, conversations with nearly two dozen improvisers bore a similar refrain: Not everyone gets them, or their jokes.

Here’s what ends up happening: Although male improvisers date both within and outside the community, many female improvisers only date fellow performers.

There’s Lyndsay Hailey, whom I sat down with one night at iO after her one-woman show, “30 Percent Chance of Hailey.”

“I tried my hardest never to date improvisers,” said Hailey, all toothsome smile, flowing brown hair and fabulous Virginian accent.

Beneath her polite veneer, Hailey has the capacity to blare into a megaphone and rap about a man’s nether region, as she did that night.

Hailey spoke about a non-improviser she dated for 18 months. Last Halloween, this boyfriend decided he and friends would dress as Michael Phelps’ relay swim team, in matching Speedos and warm-up suits. Hailey wasn’t feeling well and hadn’t planned to go out, but grudgingly joined the boys last minute. Scrounging around her apartment, she found khaki pants and brown twine.

“I’ve always done funny, never the sexy Halloween costume,” she said. “So I decided to be human hair. I wore a sign that said ‘Team USA’s back hair.’”

When the boyfriend saw Hailey’s outfit, he said: “What the hell are you? Why are you always trying to embarrass me?”

Hailey called that night “awful.” She had complained to her closest friends for some time about this boyfriend, how she felt suppressed and couldn’t be herself. “It just wasn’t fostering a creative environment for me.”

At any given moment, 3,000 students are enrolled in improv classes in Chicago, the “big three” being The Second City, iO and Annoyance Theatre.

“You immediately have so much in common. You’re in the same world, know the same people, seen the same shows, probably studied with the same teacher,” said Jennifer Estlin, executive producer at Annoyance (she and Annoyance founder Mick Napier have been together for 14 years).

But there’s a deeper, more intrinsic reason that attraction might occur. It’s based in the tenets of improvisation itself.

“There’s a connection in class,” said Conner O’Malley, who met his girlfriend Aidy Bryant a year ago while performing. “You learn a lot about someone when you’re performing with them. An improv scene isn’t my scene or the other person’s scene. It’s our scene.”

Over lunch at Wrigleyville’s Uncommon Ground, Jet Eveleth recalls a recent conversation she had with her mother.

“She was concerned. I just had a relationship with an improviser end a few months ago, and she noticed a trend,” Eveleth said. “She said, ‘Do you think you’ll only continue to date comedians?’”

The redheaded Eveleth exudes a 1950s Life magazine elegance about her. So it can be jarring to watch her perform – debonair one minute, caustic the next, a whirlwind of physical comedy and pretzel contortions.

Nearly all of Eveleth’s female improv friends, she said, are dating improvisers. And with the exception of a few men (who were the artistic type anyway), it has been the same case for Eveleth. At one point, she had a three-year live-in relationship with an improviser on her team.

“I’m attracted to artists and comedians because I don’t want to be strange,” said Eveleth, who began a relationship last month with an improviser she has known for seven years. “I want to be able to laugh, and I want to be able to elicit laughs. It’s important that the relationship goes both ways.”

The prejudice can be true of even other women. One of Eveleth’s best friends is Holly Laurent, and the two have performed at iO’s “The Reckoning” for the past eight years. A woman walked up to her after a show several weeks ago.

“She said, ‘You and Jet were really funny. You really made me laugh, and I don’t think chicks are funny,’” Laurent said. “Sometimes it feels like a bit of a blow, but at the same time it puts a fire in my gut to make them laugh next time.”

In 2007, Vanity Fair contributing editor Christopher Hitchens wrote a piece titled “Why Women Aren’t Funny,” a column name-checked by those I interviewed no less than a half-dozen times.

The headline was predictably provocative, but it’s hard to ignore several points he makes.

The central thesis, he theorized, was biology: It’s in men’s DNA to impress the opposite sex, while women don’t have to work as hard the other way around. To make someone laugh is to trigger an involuntary response in humans, a powerful trait indeed. The ability to make women laugh is one tool Mother Nature has gifted us, therefore, men are funnier than women, ipso facto, women aren’t funny (Hitchens’ words, not mine).

By the time Lyndsay Hailey’s boyfriend reacted to her Halloween costume, Hailey knew the relationship was heading south. All along, friends dropped hints that she had another suitor.

Hailey had known of Michael Patrick O’Brien, who was starring on the main stage at Second City and is now a writer for “Saturday Night Live.” Newly single, Hailey attended his one-man show at iO. It was her first time out of the apartment since the breakup, and she wanted to feel good about herself. Bear in mind, standard women’s attire at the theater consisted of jeans and a shirt.

As O’Brien remembered that night: “I told the lighting guy, ‘Whoa, red tights just walked in!’ She had yellow boots that stood out, some sort of dark gray dress.”

That meeting turned into conversations over Facebook. The back and forth went on for weeks, with little movement. Then at 3 a.m. one Friday, O’Brien texted Hailey. He wrote: “I’m standing outside your apartment. Let me in. I have to pee.”

“In that moment, it was funnier than it was creepy,” she said. “But Michael walks that fine line with his comedy constantly, which is why I was so intrigued.”

She let him in. They stayed up all night, talking at the kitchen table until the sun came up. It has been six months now.

She said, clutching O’Brien’s hand, “I think he’s the funniest person I’ve ever met.”