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 a beautiful September evening, the kind that makes you feel lucky, like you’re squeezing one more warm day out of summer. I was walking the loop in Central Park with a close guy friend of mine, talking about change: from the colors of the leaves to the tide in my dueling end-of-summer romances. We talked about Boy A, whom I'd known for almost a year, dated off and on, and was on the cusp of turning a more serious corner with, were it not for Boy B. We had only been on a few dates, but like the dog days of August when we met, things were hot and steamy.

After the walk, when my friend and I got off the subway in my neighborhood, I had a voicemail. "Ms. Shupak, please call us back—we have a flower delivery for you."

I called them back and they agreed to re-deliver in fifteen minutes, every second of which my friend and I spent debating, pondering, hoping that it was Boy A. It had to be.

When they arrived, I couldn't believe what I saw. A dozen red roses, stems cut off, packaged perfectly in their own miniature garden. My friend and I stood back from them, staring them down in confusion and bewilderment, as if they were a UFO that had just landed inside my apartment.

Wow, Boy A was really ready to do this—to admit to both himself and me that he had real feelings, and that we should be together. 

Hope can do a funny number on that left logical side of your brain.

As you may have figured out—faster than I did that day—the roses were from Boy B.

I snapped a photo on my iPhone and sent it to five friends with just his name in the text.

All parties polled—male and female—replied with the exact same message.



Red roses are lovely, as are pet names that you might use with the woman you’re fond of. Emailing and texting sweet reminders of a shared night are both smart moves as well. But doing too much too soon at a courtship's beginning can do more harm than good. 

Instead of thinking that you’re really into her, a woman will think that there's something wrong with you. Red roses are red flags that indicate desperate Stage 5 Clinger more so than Mister Casanova. I'm not saying to stop the chivalry and romance. No, I am a champion of those two strategies. But know your girl and take your time.

Relationships are not meant to be flash-fried. Treat them more like a Thanksgiving turkey than a plate of greasy french fries. The latter tastes good going down, but the satisfaction, just like the time it took to cook, is gone in an instant. Then you are slugged with regret.

The former however, you baste all day with the sweetest of juices, watch as it turns a golden brown color, then savor every bite when you finally sit down for dinner. The advantages of a slow-cooked bond, like the day you spend tending and caring for that big 'ol bird in the oven, are long-lasting.


Verbal red roses are just as dangerous. Women get turned off if you say too much too soon. I had a guy text me after our second date, "Good night, Jamiepoo."

I never responded. We never went out again.

Sure, there were other factors at play, but come on, man. Use some of the tools in your arsenal to win her, but please—please—save some of the goodness for when you actually know and like each other.

Build the anticipation, flirt with her by not showing all your cards at once, and she will see naturally that you're a romantic dude. Shove it down her throat too soon and risk your otherwise good intentions backfiring.


Pretend you have other options. Better yet, have other options so you’re not feeling like all your eggs are in one basket.

That will help you to take it easy. Be a gentleman. But don't go overboard or you will freak her out and lose her.

Sadly, that was exactly what happened with Boy B. I called and thanked him for the red roses that night because it was a very thoughtful gesture. 

But my friends were right; it was aggressive. For that and other reasons, we never went out again. 

And I never told Boy A that I wished it were him who sent the flowers. Until now, that is. 

Next Week: Jamie says, Nice is making a comeback