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 dating scene after the painful breakup of a 10-year relationship. In her weekly column she’ll share her war stories and offer her advice and admonitions.

It was cocktail hour at my close friend’s black-tie wedding this past weekend when I ran into a guy who I'd gone out for drinks with once. He was attempting the tricky balancing act of vodka on the rocks in one hand, plate piled high with hors d'oeuvres in the other, so I took the initiative. “Oh, hi. You look nice,” I told him as I leaned in to kiss him on the cheek. He smiled. “You look nice as well.” I introduced him to my date, and just then a cracker slipped off his teetering plate, allowing for an easy exit. I bent down to pick it up and told him I’d see him inside the party.

He was just as I remembered from a few months earlier when the bride and groom had set us up: a really nice guy. I couldn’t say one bad thing about him; there was nothing wrong with him at all. He just didn’t have that je ne sais quoi.

I can’t help but think that being labeled a nice guy is the kiss of death. The word "nice" has become meaningless through overuse. I can hear my mom now, circa 1988, leaving the three of us kids with the babysitter so that her and my dad could go out to dinner: “Be nice to your sister.” Or one of her more famous Helen-isms, “If you don’t have anything nice to say, don’t say anything at all.”

Think about that guy in the office, you know the one I’m talking about: the one who always gets the days off he requests, or has the inside joke with the boss, all because he does whatever it takes to get ahead. Being nice doesn’t always pay off at work; likewise at rush hour, trying to get into the Lincoln Tunnel. You let one too many cars go ahead of you as those eight lanes converge into one and then there you are, Mister Nice Guy, the first car behind the ambulance when they close it for an accident inside the tube.

So in this whirlwind race we call life, is it better to have an edge? Do we want that edge in a significant other? Maybe we need that edge. Seeing this guy at the wedding got me thinking about being nice. When it comes to dating, do nice guys finish last?


I dated a guy for a few months in college who we all dubbed the nicest guy ever. He called when he said he would, cooked whatever I wanted to eat, and was always Mister Polite to all my friends and family. I dragged him to visiting day at my overnight camp, tormented him by living near my ex-boyfriend for the summer, and then, after buying me a gorgeous necklace that my MTV News intern salary could never afford, I dumped him. You know what everyone said? “But he was such a nice guy.”

Almost a decade later I still believe that on some level nice equals boring. I need a little sass, edge, and mystery to hold my interest; that’s not to say I don’t still want you to be a gentleman. Please don’t ever underestimate the power of manners. I know what you single guys are thinking though, that it seems like a double-edged sword. Girls profess to want niceness, but then why does it seem that the guys who play games are the ones who get the girls? And if a guy is too good, the girl gets bored.

It’s a fine line. Any guy with any kind of game knows that dating is a tight rope you walk, trying to balance chivalry with aloofness. Where you begin to wobble is when the woman equates your excessive niceness with a lack of sexuality. It’s the flirting, teasing, pushing at a woman’s boundaries that will cue her into thinking you’re interested. If it’s always whatever she wants, if you show no backbone, independence or confidence, she will lose that desire to play. Flirt with her. Express real, tangible interest and desire. That’s what creates the back and forth game that will help keep the anticipation going and, by proxy, the relationship. When you stop playing, your arms start flailing in the air and then you’re falling off that tight rope.


A few weeks ago I was having dinner with a friend of mine when she confessed that the guy she liked the most right now was one she had only hung out with three times over the course of three months. “How much I like him is totally disproportionate to the amount of time we’ve spent together.” She said she felt silly saying it, but her admission gave me the confidence to share a similar story. I told her that the most intriguing guy in my Rolodex right now is one I’ve hung out with even less—just twice in three months—and only communicates with me via text. Compare that to some of the other guys in the picture, ones who call to see how my day was, mail me magazine clippings to make me laugh, always make plans to hang out, and you might call me crazy. My friend and I shook our heads at each other, blown away by the fact that guys who are incapable of making plans to get a drink occupied the brain space of two otherwise smart, successful women.

Sometimes we can’t help but be drawn to the mystique of an elusive guy—one that we should never be giving the time of day. The fun of the chase definitely gets our attention and keeps us interested, but only for so long. Earlier in our twenties it was butterfly-inducing, exhilarating, and we fell for it. Now we laugh about it over dinner, but these guys won’t last much longer, if at all. They’re fun for now, but they’re not guys we would ever consider dating seriously. We’re adult women looking to be with adult men, not boys.

So don’t get discouraged single guy, keep being a gentleman. I know many of you have seen the kind of guys I just described playing with your female friends’ heads for years, and you just don’t get it. You think the games other dudes play are distasteful, immature, or just not your style. I say challenge yourself to keep opening doors and complimenting a woman you like, but sprinkle in a little sarcasm and flirting. Don’t forget that you have to telegraph your desire—a desire to date and be intimate, not brotherly or just friendly—to the woman you’re interested in. We don’t read minds or smoke signals. Create just that little bit of tension and I think you’ll be pleasantly surprised by the results.


When I told a close guy friend of mine about this column and asked him about nice guys finishing last, he said maybe in junior high school, but not as adults. My thoughts precisely; nice.

Next Week: Jamie discusses why some people are doomed to repeat history.