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.

I was at my friend’s lake house for the Fourth of July and one of her single guy friends asked if we had any single girlfriends for him. Because I'd never met him, I asked what he was looking for, even though I was banking on some cringe-worthy response like “Someone hot,” or “Got any blondes?” 

Instead, he said, “I just want a woman. That’s it. I’m good for any single female.”

I was gobsmacked; these were hardly the musings of a seemingly young, confident man. If you’re thinking this guy is desperate, then you’re thinking what I was thinking—but that's not correct. “I used to have a type," he explained, "And it got me nowhere. All it did was lead to bitchy girls.”

Imagine that. Some of my guy friends have jaded me into thinking this was a never-ending cycle: they say they want a girlfriend, but then only date girls whose best assets are, well, their assets, and are then shocked and bothered that said girl is a personality-less bore. It’s like going to the Palm, ordering your filet well-done, and then complaining when it comes out grey inside.

What I loved about this guy at the lake house was that he had learned his lesson. Sure, we finally got him to own up to having a type—he loves leggy blondes a la Carrie Underwood (who doesn’t?)—but he was ready to test drive the theory that perhaps personality and a career can also make a woman interesting. He didn’t want to repeat his dating history and wind up with another “bitchy girl,” and I don’t blame him.


Some of us have pretty horrifying ghosts of dating past. When we study terrifying events from world history, we are taught from a very young age about how easily history can repeat itself. I can still hear my Hebrew school teacher now, saying the only way to prevent something from happening again is to educate ourselves about why it happened; it’s the remembering, the honoring, and the teaching of it that will keep these obscene events from happening again. The same principle applies to dating.


A friend of mine emailed me not long ago to say: I dated the same broken record of guys for years. Maybe one worked construction and another was a bartender, but really they were all the same—undependable and selfish.

While my eyes rarely meet a construction worker they don’t like, let’s get to the real root of the problem here. We too often point the finger at the other person because it’s so easy to say, “It was you, it’s all your fault.” I’ve been there, I’ve done that, and all it did was leave me with a broken heart. That’s because the problem wasn’t the other person’s behavior (though it did leave something to be desired), it’s that I was letting them behave and treat me that way. So here’s what you need to do, single guy. If you find yourself in a situation that feels all too familiar, like maybe I’ve been with this kind of woman or I’ve felt this something-isn’t-right twinge in my stomach before, stop pointing fingers and take a good hard look in the mirror. It’s not her; it’s you.

Ask yourself this: Why am I dating this kind of destructive person again? Why am I letting her treat me this way? What attracted me to this person in the first place? What’s the real reason why this relationship isn’t working? Was I in it for the wrong reasons?

I promise that once you can take a big enough step back from it—and her—and answer these questions truthfully you won’t make those same mistakes again. You can change the course of your own dating history and make much wiser decisions about the next woman you get involved with or start dating seriously. I know because I’ve done it.

The toxic ones are always going to be there. It’s about learning to recognize them—via patterns, personalities, and habits—and not letting them have their way with you again. People often ask me if I think I’m going to have trust issues or worry about being cheated on again. Luckily, I can laugh to myself a little about it now, because it’s actually the total opposite. I can now smell an ego or self-absorbed dude from a mile away. It’s like someone is waving a giant red flag in my face and I need no other cue. I’m out of there. I used to dig that kind of confidence in a man. But I know better now. That’s not how a real man shows confidence; it’s through humility and grace.


We all have a friend who has a type. Maybe he’ll only date brunettes, or girls from the South, short girls, curvy girls, you name it. I think it’s because I’m attracted to personality and not a specific look that this forever fascinates me. Like the guy at the lake house, you have to let go of that ideal a little bit if you don’t want history to repeat itself. If you endlessly pursue those physical qualities instead of the qualities that make for a real relationship, you’re not being fair to yourself. What’s so tricky about relationships is finding both—the ability to feel physically and emotionally close to that one person. It’s this tough interplay between what might immediately attract you to a person and whether you can also be friends with them, simultaneously. Finding the right balance is always difficult, and I’m not suggesting you sacrifice those specific qualities or characteristics in a woman that turn you on. But maybe you haven’t been as lucky in love because you haven’t been as open-minded as you could be.

Whatever has gotten you into trouble in the past, whatever has led you down the long ugly road to heartache, it’s time to honestly reconsider what you want in a woman. As soon as you tell yourself that you deserve better than what your dating scorecard historically shows, that type of woman who’s been detrimental to your heart all these years will never be able to hurt you again.


I’m still looking for a girl to set the guy at the lake house up with. I want to find one who’s fun, smart, and ready for a good guy. And who knows—maybe she’ll be a Carrie Underwood look alike after all. We’re not trying to completely rewrite history here.

Next week: Jamie discusses being the last man standing