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.

A wise man once told me to pretend that you are driving without a rear view mirror. As a traffic reporter, I would never advise this. In dating however, it's a totally different story.

This was easily the best piece of advice I got when my engagement, and 10-year relationship, ended last September. You may think, as I did, that a decade of your life, a diamond ring, and a promise mean something, but in this case, it didn't. My life was turned completely upside down, but now more than 6 months later, here I am, living far better than that girl back in September ever would've expected.

Dating is Like Rush Hour...

Being on the New York dating scene for the first time is a lot like the morning commute on the 6 train: sometimes it’s an easy connection, and other times, a total train wreck (well, not literally). I'm no expert, but I've been lucky enough to meet some really interesting guys and go on some really fun — and not so fun — dates. And that's why I'm here: To share what's worked, and what hasn't.

My experience is my expertise, and all the examples you'll see in my columns are real: actual excerpts from emails, text messages, and g-chats I’ve received from guys. Tune in every week and let's see if I can't help you read the women in your life as successfully as I read you the delays at the Hudson River crossings. That wise man by the way, is my Dad. So far, he remains the main man in my life. (For now.)

Since I'm introducing myself to you, it only seems appropriate that the subject of my first column be my Dos and Don'ts for the Perfect Email Intro. Whether it's that girl your friend's setting you up with, the one you met at the bar Saturday night, or the one you've been eyeing on match.com, follow my 4 simple steps, and I guarantee you stir up some electronic chemistry. That’s almost like real chemistry, right?


Seems simple enough, right? Check out what one guy wrote me:

"Hey Jamie, my name is ___ and I got your email address from my friend ___. I hope you know him :) I went to college with ___, whats your connection to him? So how are you? Where r u from?"

What he did isn't wrong or horrible in any way, but there's just a much better approach. Don’t ask me where I’m from in an opening email. I feel like I'm on an interview, and even worse, now I'm bored. I have to wonder too, is the "I hope you know him" a joke? Is that why there's a smiley face after? Painful. We are both aware that we both know the friend. He set us up. You don't need to explain in depth how you got my info, I'm sure you already know my connection the person, so just try this:

"Hey Jamie, it's ___, ___'s friend from college." Then move right along to #2.


After the initial hello, show me what you got. Say something funny, witty, interesting... FLIRT a little. Make me smile, make me laugh, give me a glimpse into your personality. Use anything you know about me, and play on it. These are good:

"Hey Jamie, I'm ___, ___'s friend from college. So glad he gave me your info cause he told me you're an Eagles fan and I'm sure you could still use a drink after the end of that season."

"If I'm late because the BQE is bumper to bumper or the FDR is a parking lot, I'll bet you believe me."

Usually I'm against traffic jokes, cause it's so obvious and easy, but for some reason this one worked. Maybe because this is actual traffic lingo I would use? Or the rest of his email was good, too? Regardless, he's using what little he knows about me, and playing with it.


Now that you've made me laugh, go in for the kill. Make your move. Suggest a day and/or place to get a drink. This guy was perfection:

"Are you free Thursday? I love Brandy Library... have you been?"

Score! A win-win situation. I can very easily look at my calendar and see if I'm free Thursday, then great, you're in. If not, it forces me to pick another day and say something like, "Thursday is no good but how about Friday?" It's super simple for me...and a definite yes for you. Don't ever leave it open-ended. It makes you look disinterested and lazy. Always suggest a day and place for the date and the girl will love you for it.


Again seems simple enough, right? Not always. Look at this guy:

"I would like to introduce myself and give you a call, communicate via email, and/or meet up for a drink. Let me know what you think."

Okay, woah, this is just way too much. We're already communicating via email, right? And who says it like that? If you want to give me a call or meet up for a drink then for the love, say so. Even worse:

"Let me know what you think."

You want to know what I think? I think you're lame for saying "and/or meet up for a drink." I mean, I hope it's and. Isn't that the whole point here? Less is more, so just end it. Say something short and sweet like, "Can't wait to hear from you," or, "Looking forward to meeting you." Lesson learned: the best approach is a simple one: say hello, say something funny, suggest a day to meet, and get out.

Next Week: Jamie shares three things to never do on a first date.