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.

Hands down the best date I ever went on—and by proxy, one of the most fun nights of my life—was when I went to the Eagles/Giants game with this guy back on a beautiful Sunday night in November. We had been friends for years but this night changed everything. He brought me to our favorite place (the Linc), to cheer on our favorite team (the Eagles), just steps from one of my favorite sportscasters (Al Michaels)—it’s not hard to do the math. I was in heaven.

If you’ve been reading my other columns you know that I’m a rabid Philadelphia sports fan. You’ve seen the texts and emails from guys I’ve dated—some that have helped them score; others that have gotten them cut—so this guide has been in the works for some time now. Let’s be clear though: not every woman is a sports fan. This is what works for me, a girl who grew up the middle of two brothers, who always preferred football in the street over playing with Barbie or an Easy Bake oven. So, if you ask me, dating a female sports fan is fun. What’s even better? It’s so easy. (Flag: intentional bias)


The beauty of sports is that no matter what season or day of the week, there’s always a game on. So you can’t afford tickets to the Rangers-Capitals playoff game next week? No problem. Here in New York, that’s why people take the 7 train to Queens, to go see the Mets. Get this: there are tickets to next Tuesday night’s game versus the Astros for as low as $15. Fifteen bucks? That’s almost the same as a movie ticket, and I don’t care how hot Jake Gyllenhaal is, Source Code will be streaming on Netflix in 3 weeks. Let’s go to the game instead. I know my nephew’s t-ball team is more exciting than both of those squads combined, but going to the game is exponentially more fun than meeting you for another night of dinner and drinks in the West Village. Snooze.


I had plans to go to a new wine bar in the neighborhood with this guy and when he came to pick me up I called an audible, suggesting we go to Barrow Street Ale House instead. I mean, come on…the Knicks were playing the Heat, Maryland was playing Duke, and I knew I’d be fidgeting to check scores on my ESPN app between sips of Cabernet (which we of course know, is a big dating don’t; the phone-checking, not the wine-drinking). He was thrilled, and admitted to wanting to watch the games too, but being scared to suggest it at the risk of looking like a cheap skate. While I respect the chivalry, as my boy Keyshawn Johnson would say in my favorite TV segment on Monday Night Countdown, “Come on, man!” (If you don’t know it, YouTube it) A true female sports fan wants to watch all the games, all the time…so don’t be scared to suggest the sports bar. I’d personally rather have beer and wings than edamame dumplings at Buddakhan. Well, you get the point.


It gets a little more complicated when the guy doesn’t know how many points a touchdown is worth. I dated a guy once who not only didn’t follow sports, but also, wait for it…didn’t own a TV. (A future column: other areas you must excel in if you need me to explain what’s happening every time they stop the clock.) I never thought I could date someone who didn’t watch sports, but this guy proved me wrong. He checked in on the games I was watching, kept up with Adam Schefter’s twitter feed, and was happy to cheer for my teams. Win, win, and oh yeah, win. There have been other guys who pretended to be into sports, and it’s just painful. It’s like me dating an investment banker and telling him I understand how fears of a nuclear disaster will affect the Nikkei. He would call my bluff in two seconds. So don’t fake it, show interest and just follow along. Be who you are. If you’re an artist, own it. If you’re a musician, own it. If you’d rather get a mani/pedi/massage than watch football on Sunday, dude, live it up. Can’t say I’d date you, but as my Mom and her friends would say, there’s someone for everyone. Every Sunday during football season my day begins with Boomer and the boys on Sunday NFL Countdown, continues with the 1 and 4 o’clock games, and ends with Al and Cris calling the Sunday night game on NBC. If you want to watch with me, awesome…if not, that’s okay too. Just don’t knock it, or pretend to understand or care if you don’t.


A few weeks ago I told you a sure way to land a second date is to challenge me to something. Now let’s take that one step further, make it a little more interesting, and put a fun wager on the game. I dated this one guy who knew I had never tried and was actually borderline petrified of cottage cheese. (No explanation necessary.) So we bet if I lost in ping-pong that I would have to eat it. Sure enough, he brought a tub with him to taunt me, put it on the edge of the net, and when I lost I dug right in. (Wasn’t as bad as I thought.) That same guy went head-to-head with me in a March Madness pool, and this time, the stakes were higher. If I won, he’d wear an old Rodney Peete jersey of my brother’s out to dinner, and if he won, I’d wear his Eli Manning jersey. Once again, I lost, no thanks to Kansas State, Duke, and the most ridiculous final four ever. I’m a woman of my word though (remember the cottage cheese?) but sadly we stopped dating. Still, let the record show the only good thing that came out of our breakup was that it happened before I had a chance to fulfill my end of the bet.


My friend Jon cracked me up a few weeks ago when he told me that he always likes to be “the away team,” a term I had never heard before. As he so eloquently explained, it’s his preference for sleeping over at a girl’s house instead of them being at his place. “Always easier to leave when you want than to try to get her to leave,”… which got me to thinking: is this why most of the guys I’ve dated suggest bars and restaurants in my neighborhood? Am I that naïve? Well, unlike Jon, I always prefer home field advantage. I love when a guy makes it easy for me by picking a place close to my apartment. Just like in sports, I feel more comfortable and it’s more convenient when I don’t have to travel. Plus, as so many have advised me since I’ve been single, let them come to you.


The same guy who I went with to that Eagles/Giants game also sent me the Gameday book and sweat towel when I couldn’t make it to the playoff game versus the Packers. Another time he showed up at my apartment with a retro Phillies snow hat for me. Love it! Those gifts, which together break the bank somewhere around $20, mean more to me than any other present I’ve gotten from a guy. It reminds me of when I got engaged and everyone was speculating how big my ring was, asking about the cut, size, you name it. I didn’t know, and I never cared to ask him. It didn’t matter to me how many carats it was (sorry girls, I know you’re all shaking your heads)—it only mattered how much he wanted me to be his wife. And ya know what? I was proven right. There’s no rock big enough or present expensive enough to make up for lack of care, thought or character. You don’t have to spend a lot of dough, guys, trust me. Shower a female sports fan with swag from her favorite team. That's the way to her heart.

Next week: Jamie on how you guys can look your best on date night.

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