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 like the sound of her. I think you should totally invite her.”

That was the advice I gave a dear old guy friend of mine at brunch the other day. Over (my) greek salad and (his) salmon eggs benedict, we discussed the new girl he was seeing and whether or not she was holiday party-worthy.

Pro: Over the past few weeks they’d been on two great dates and in constant communication.

Con: It’s only been two dates. Was it too soon?

Pro: She has a great job and “you know how important it is for me that the woman is career-driven, Shupakala.”

Con: She just started this big, new job. Will starting to date someone be one thing too many for her right now?

Pro: Instant street cred with the boys because she’s “super hot.”

Con: But would there be another girl at the bar he’d want the chance to talk to?


’Tis the season for holiday parties, whether through the office, family, friends, or otherwise. Then there’s New Year’s Eve just a few days later. It’s a joyous time of year, with lots of drinking, catching up with old friends, and kissing under the mistletoe.

It’s special to be able to share it with someone, but how do you know when to invite that new woman you’re dating? It can be both exciting and exhilarating if it’s the right time, or stressful and even burdensome if you extend the offer too soon.


There are two important things to consider before you make this decision. First is the caliber of the event. A festive gathering at a friend’s apartment is an easy, casual way to introduce her to your people. Everyone is comfortable with one another and there shouldn’t be too many hardball questions thrown her way. But you might want to take the bunny slope—go a little easier—if we’re talking about a soiree at your parents’ place or your office holiday party.

Sure, everyone is in a celebratory mood and plenty liquored up on candy cane martinis, but there are certain expectations that are more common and certainly more exaggerated this time of the year. As I wrote before Thanksgiving, family wants you to fall in love, get married, and make babies. “Casually dating” and “taking it slow” are not in their lexicon when the stockings are hanging from the mantle or the menorah is out on the kitchen counter.

Which brings me to the next consideration: Is she someone you’re just having a good time with, or is this a woman you’d actually like to date? If it’s the former, it might be easier to bring the woman along because the expectations are low. You can both just relax and have a good time. However, if she is someone you could see yourself with, you might not want to rush it. The pressure is high, as are the expectations, so make sure you’re on the same page before extending the invite. Still, if it feels like the natural progression for your relationship and both sides are requesting to meet one another, then who am I to object?


If you decide to bring her along, keep a few things in mind. Some women might view a holiday party invite as a sign of commitment. True, some women will see anything as a sign of commitment. (I have a friend who once famously said, “But he butt-dialed me! That means I’m at the top of his recent calls.”)

Make sure you’re on the same page. While a plus one can sometimes be an indicator that she’s more special, or that you’d like to take things to the next level, it could also mean you just want someone to talk to by the punch bowl or use to show your ex that you’re not alone.

Communication is key here because it is so easy to give and receive mixed signals and the wrong impression. The last thing you want to do is hurt her feelings and ruin a chance at a future with her.


Even though I really wanted to meet her, my friend decided not to invite the new, “super hot” girl he was seeing to the holiday party. I get it; he made the right decision.

He thinks she has some long-term potential, so he didn’t want to rush it or bombard her with all his inquisitive friends (not me – no, never). He also wanted to hang out with her one more time, just to reconfirm what he’s been feeling for her.

’Tis the season for cozying up by the fireplace with your woman. Don’t ruin it by throwing her onto the coals with your family and friends too soon.

Remember, there’s always New Year’s Eve.

Next Week: Dear Jamie, Home for the Holidays edition