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Here’s How to Be Funny on a Date

Step 1: Never read anything about being funny on a date

It’s important for a man to be funny on a first date, right? Everyone says so! Men’s Health claims 77 percent of the women it surveyed counted a sense of humor as the number-one personality trait they look for in a man. Being funny is number three on Elite Daily’s list of “What Women Really Want!” And over at Business Insider, sense of humor checks in at number two among its “11 Qualities in Men That Women Find Attractive.” (“A sense of humor is important to women. Scientists have found it makes men seem more intelligent,” crackles the entirety of the blurb.) Cosmopolitan even claims that your ability to make others laugh directly corresponds to how good you are in bed: “Unsurprisingly, women who found their partners funny had more sex with them and more frequent orgasms.”

Leaving aside the question of whether any of this is even faintly true, what if… you’re not funny? What if, despite all your other admirable qualities, that one attribute has bypassed you completely? How will you impress your date if you’re unable to spontaneously make a witty observation, land a delightful pun or even make it through a knock-knock joke on your first attempt? As someone who has performed and produced stand-up, sold sitcom scripts and edited the comedy section of a popular New York magazine, I can confidently tell you: Fucked if I know!

Being funny is certainly a skill you can hone (as Jerry Seinfeld is fond of saying, you have to do stand-up for 10 years before you can even call yourself a beginner), but it does require a basic natural inclination. You can spend three decades teaching a stiff-fingered, tone-deaf man to play the piano, but it’ll never sound quite right. The same goes for providing comedy instruction to a man whose funny bone was surgically removed at birth. As hard as they try, it’ll always be as convincing as Arnold Schwarzenegger getting in touch with his feminine side.

What I can tell you, though, is this: Whatever else you try, never, ever look to an article about how to be funny on a date for advice. Ever. If you do, you will encounter a shocking array of the most contradictory, misguided and flat-out wrong information imaginable.

Take, for example, the very first result that came up when I searched for tips on being funny on a first date: “How To Be Funny and Humorous With Girls,” on a website called I Help You Date. There were several things that surprised me about this article, although perhaps none more than the fact that it turned out to have been written by a San Francisco-based dating coach and not, as I first suspected, something run through Google Translate after being hammered out by a content farm in a distant country:

To in reality turn out to be a funny particular person whose firm everybody loves, you need to take child steps into changing into a greater you.

Okay then!

Despite the inclusion of helpful tags such as “alpha male,” “inner game” and, uh, “terminology,” navigating this 2,000-word collection of random nouns and inexplicable conjugations was very difficult. But as bad as the article is, it’s not light years worse in its actual advice than supposedly more reputable sources of information.

As an act of public service, I’m going to run through some of the most egregious and baffling pieces of advice that keep popping up in these articles.

#1: Tell Jokes!

A favorite saying of one of my first editors was this: “If you tell jokes, you’re not funny.” He was 100 percent correct, yet so many dating advice-givers claim the best way to make your date laugh is to keep a stash of crappy old gags on file in your brain.

“Learn quite a few jokes — jokes and funny one liners provides you with a lot of catchphrases that that [repetition theirs] you must use yourself,” advises I Help You Date. “Practice jokes ahead of time,” says WikiHow in an article called, “How To Make a Girl Laugh.” “Have a joke pool — if you’re at a lame party … a reserve of jokes can come in handy,” explains Ask Men in its contribution, “How To: Be Funny.”

Let me put it this way: The words, “Oh man, I heard this great joke the other day…” serve but one function, and that’s to bring formerly lively conversations to a grinding halt, the faces of those present freezing in a rictus of resigned awkwardness as the atmosphere is smothered by some witless goon’s attempt to recite a joke to which they only now realize they don’t fully remember the punchline.

Now picture your potential date’s very soul howling in dismay as you recite your collection of tried-n-tested one-liners.

Please, men. Please don’t do this.

Of course, I Help You Date claims that knowing lots of jokes will help you in other ways, too:

It’ll additionally can help you visualize eventualities higher on your own existence.

Good to know!

#2: Do Some Slapstick!

“You can use a number of different elements of slapstick to get laughs from your girl,” insists WikiHow. “Use falling, double takes, slipping, tripping and collisions to your benefit.” Because there is truly no greater way to make a good first impression than by reenacting the opening scene of Naked Gun in the middle of a crowded restaurant.

#3: Launch Into Random Bits!

Anyone who’s dated an aspiring stand-up will recall the cold, sick horror of realizing that every other conversation ends with them trying out a new bit on you. And yet, almost all of these articles recommend going to comedy clubs and noting what comics do onstage to get a laugh, then applying that to your date (“Watch some stand-up comedy shows to get a feel of comedic timing,” says WikiHow. “Keep notes of anything funny that you think might work in your situation.”)


No, no, no.

Stand-up routines only work in context, i.e., in front of a paying (or at least drunk) crowd of people who have chosen to see a stand-up comedy show. They do not work anywhere else.


You know when your annoying coworker starts reciting an entire bit from a Netflix special he just watched and no one laughs? That’s only partially because he fucked it up. It’s mostly because stand-up is, by its very nature, designed to be one-way. It’s a pact between the audience and the comic — the comic speaks, the audience listens. It doesn’t work in any situation in which both parties have equal right of speech, and your date is absolutely not obligated to listen silently while you recite your carefully rehearsed five minutes on how dogs be like this, but cats be like this! And even if they do, they will not laugh, because that isn’t how it works.

Aspiring stand-ups, this goes double — triple — for you. Because you should know better.

#4: Ask Wacky Questions!

“When you’re on that first date. And there’s that awkward silence. Because none of you knows what to say. Don’t worry, we got you!” says Z!Koko’s article, “22 Hilarious Questions to Ask on a First Date to Help You Really Get to Know Your Date.” Somewhat impressively, this article’s author has less of a grasp of what to say on a first date than they do of how to use a period. Here are some of their suggestions for livening up that frosty dinner date with a hilarious line of interrogation:

  • Have you ever been, like, sexually attracted to a piece of fruit?
  • How big do you think Thor’s penis is, just like, scientifically speaking?
  • How many murders have you witnessed?

There’s no way that last one could backfire, right?

#5: Make Sex Jokes!

“If somebody around you says something funny, try to find a hidden meaning which can be associated with sex,” says I Help You Date. “And answer back to the to the [repetition theirs] question or the comment keeping the sexual reference in mind.”

There are no words for this level of wrongness. Move along.

#6: Show Her Funny Things You Found on the Internet!

“Have a collection of funny material that you can send her,” advises WikiHow. “Find a website that specializes in sweet pictures of animals doing funny things, such as kittens sitting in a shoe or piglets in boots. Send her some of the photos to make her laugh.”

It’s never clear if this is something you should do to break an awkward silence during the date, or if it’s essentially an icebreaker to ask for another.

Either way, the message is clear: PIGLETS IN BOOTS WORK EVERY TIME.

Look, I don’t know what to tell you. Maybe being funny isn’t actually all that important? Maybe just being, like, a good dude who doesn’t act like a creep, who listens to and takes interest in the things his date has to say, who handles his shit and treats other people with care and respect, is all more important than painstakingly memorizing a complicated equation for tricking others of your species into finding you amusing? All these same bullshit lists that say women only like funny men also stress that confidence is a massive chunk of the puzzle, so you could just try being confident in your un-funniness.

Y’know — be yourself.

Then again, maybe not since you could be a major asshole.

All I really know is that literally anything’s better than trying to use the advice in these articles.

Sorry, man.