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 think we’re too young to be so serious. I love you and don’t want to be with any other girls; it’s not about that. I’m really confused and just need some space.”

I’ll never forget the night back in February of 2002 when my boyfriend of two years fed me that line, dumping me just one week after Valentine’s Day. He had just bought me jewelry and told me he was going to love me forever. If you had looked outside my second floor room that night, you’d have found my heart somewhere on the pavement, smashed to pieces by his cowardly excuse for a breakup. Confused? Needs space? Not about other girls? As soon as I realized that it was, in fact, only about other girls, I went out and met another guy. We dated for the next few months, but it wasn’t even that long until what’s-his-face came crawling back.

He was on a mission to get me back, and came equipped with all the right lines. He hadn’t slept with that girl in my writing class or stopped loving me, even while flirting with every girl in the bar. Or the one I could have used to pen a book entitled How to Get Your Ex Back—that he would never hurt me again. I leapt back in his arms faster than my 20-year-old self could chug a beer.

Fast-forward nine years to this past September and there we were again. Same guy, same cowardly “I just need some space” routine, but this time with so much more to lose—we were living together, we had a dog together, and I had a ring on my finger. Difference was, I had grown up. I gave back the ring and moved out.


Familiarity and comfort in a relationship are qualities a lot of people crave, but allow me to be your cautionary tale. There’s a reason why an ex is an ex. I was young and in love, so I believed him when he promised he had changed. Circumstances and situations can change, the weather and your weight can change, and while a person can grow up and mature, I’m not sure their core values ever really change.

We’re taught from a pretty young age about the benefits of recycling, to try and use old glass, paper, plastic, and electronics to make new versions of the same product. It’s crucial to saving our air, water, and planet. But when it comes to dating, should you leave your ex in the proverbial landfill, or try to recycle her? And what about a friend of an ex, or the ex of a friend; do the same rules apply?

Click to the next page to find out.

A few weeks ago a guy took me on a date to the Mets game. We talked the whole way there on the 7 train, laughed our way through a couple beers and tacos, and before I knew it, it was the ninth inning. We took two subways back into Manhattan, he walked me all the way home across town, kissed me on the cheek goodnight, and told me he’d call me tomorrow.

It was a really fun night with a really great guy—he’s smart, fun, funny, good-looking, and has impeccable manners. By all accounts it was a fabulous first date. Except I already knew him. The guy I dated for those few months in college before I got back together with my ex? It’s his friend and former roommate. Even though it’s been almost nine years, I still got that icky feeling inside. I still talk to the ex-boyfriend, almost everyday in fact, and he’s more a close friend and confidante now than an ex. He even gave me his blessing and told me he didn’t mind if we date. But hanging out with his friend that night, I just couldn’t shake the stigma of their connection.

We have plans to hang out again, and I’m going to give it another chance, but I’m not convinced it’s okay to recycle an ex’s friend. To pick from the recycling bin of an ex’s friend, I think you have to be overwhelmed by the connection—like this is the perfect woman—to make your eco-friendly intentions worthwhile.


There was another guy I went on a few dates with who I really thought I liked. He was charming, with classic good looks, impressive job, and equally impressive apartment. One of my best friends had gone on a few dates with him a few years ago, but it was never anything serious. Naturally, when I had dinner one night with her and two of our other close friends I was gushing. Normally the best friend would be right in the conversation, hanging on to every detail about what he said, where we went, and when we were going to hang out again. This time, she sat staring with an uncomfortable look on her face—one I was neither used to, nor expecting. When she did speak up, it was to recount all the nasty reasons why he wasn’t right for her, and in turn, wouldn’t be right for me.

I thought because a few years had passed, because they were never boyfriend/girlfriend, and, most importantly, because she was now happily soon-to-be engaged that it wouldn’t—shouldn’t—matter. I was wrong.

Even though I’d just finished a delectable plate of ravioli in vodka sauce, I left dinner with a bad taste in my mouth. I never would have entertained this guy coming on to me if I thought it would upset her in any way. We hashed it out over email the next morning, and I took her warning in stride. We agreed that I had to see for myself. A few weeks later, I ended things with him. Everything she had told me about him was right.


In the end maybe recycling is best left to soda cans, water bottles, and old batteries. While there are no hard and fast rules about recycling in the dating world, I’ve learned that there’s usually a good reason why it didn’t work out the first time around.

REDUCE the amount of times you get hurt by doing your best to recognize a woman with bad intentions or bad behavior. REUSE an ex only when you trust she is genuine about how she’s going to do things differently the next time around. And let’s agree to only RECYCLE a friend’s ex after checking with them first.

Next Week: Jamie goes to dating boot camp and shares what she learned.