Jamie Shupak is the Emmy-nominated traffic reporter for NY1, the Big Apple cable network that’s the end-all and be-all on all things Gotham for New Yorkers. She’s also a beautiful, single woman navigating New York’s treacherous (and hilarious!) dating scene. In her weekly column she shares her war stories and offers her advice and admonitions.

Last Valentine’s Day I received presents from three different guys. (I know; I was a baller back then.)

Dude #1 played it like the classic romantic he is, dropping off a bag of candy at my office with a note that read, “From the guy you beat in ping pong, but who beat you in Scrabble, happy Valentine’s Day.”

Dude #2 tugged at my heart strings just a tad harder by sending me the NFL Gameday book from the Eagles/Packers playoff game with this note: “If you were with me, they would’ve won.” 

Dude #3 emailed me a picture of himself and DJ Pauly D. from the Jersey Shore. They ran into each other at an event and were wearing similar outfits in the photo, so his email read: “Happy Valentine’s Day from Pauly D and me! Yes, we dress alike on purpose and it’s cute, dammit.”

Sure, I told my friends about all three because that’s what any woman with a pulse would do. (Don’t ever believe a woman who says otherwise.) But which one won me that day? Easy—guy number three. Why? He made me laugh.


If I had a choice to marry either Brad Pitt or Jon Stewart, ten times out of ten I would be Mrs. Daily Show.

If it were between Johnny Depp and Zack Galifinakis, I am walking down the aisle with the sexiest member of The Hangover wolf pack.

Don’t be gobsmacked, guys. Humor is hot.

If you think flashing your washboard abs or batting your baby blues will win us over, you’ve got it all wrong. You don’t have to stop doing that, but newsflash, guys: the way to a woman’s heart is through her mind.

So make her laugh.


You don’t even have to be funny, per se. Cracking jokes is great, but it’s more about letting loose, not caring as much about the little things, not being so uptight, and just having a little fun.

I can’t tell you how many dates I went on this year with guys who were nothing short of marriage material. They were smart, successful, well-mannered, interesting, and even good-looking. All good, sure, except where they were from: Lame City.

It’s simple: if you can’t make me laugh, we can’t go out again.

When it’s one of those days, and you know the kind I’m talking about—you run out of gas, your boss lays into you about a project, your sister aggravates you about family dinner on Friday—the last thing a woman wants is to have Mister Serious around.

That is the worst kind of wet blanket you can be.

What I want, what my girlfriends want, hey, what every woman I know wants, is the guy who will see the humor in a situation. It only takes two seconds to text her that funny picture or email her that link to the hilarious story you just read.

If you enable the anger and crankiness of the day, you are making it worse for your woman and, by proxy, yourself. And perhaps she’s too annoyed at this point to actually laugh, but if you can get her to smile, you win.


There are different kinds of funny and just as many ways to infuse it into your relationship. Try this: Instead of sending her that boring email confirming the details of your date, why not follow the lead of one guy I went out with? He sent me a picture of the ridiculous orange and blue Dumb and Dumber suits and asked which one I preferred him in for the evening.

I laughed; he won.

There is just no price tag to put on a sense of humor. Your bulging biceps are fun to look at and touch now while we’re young. But in 10, 20, heck 40 years from now it’s not going to be your hot body that gets us through the stress of kids, marriage, jobs, or even worse, a turn of bad health.


As for the guys from last Valentine’s Day, two of them are still good friends of mine. They still send me funny emails from time to time, and I still laugh.

One of them is a little more than a friend and who knows—maybe by this February 14th he’ll be my boyfriend.

Now that would funny.

Next Week: Jamie on Communication Chemistry