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 (and hilarious!) dating scene. In her weekly column she shares her war stories and offers her advice and admonitions.

It is one of my most favorite traditions. Every Thanksgiving morning I suit up in my long underwear and retro Eagles jersey and join my dad, brothers, and best family friends for our annual Turkey Bowl, a friendly football game played at the elementary school where my father and his closest friends first met.

The strategy, the fumbling, the bobbing, and weaving—turns out there is no better precursor— practice, even—for what comes later, when we sit down to dinner.  

Just one week from today, it’ll be time do it again. Cue the turkey, stuffing, sweet potatoes and cogent questions. Wait, what?

Holidays bring families together to celebrate, eat, drink, and to get to the real core of what we are about—interrogation.

If you’re single, it’s, “Are there any special girls in the picture?” If you’re dating just one person it’s, “So, tell us about the girl. Is she cute? Is she smart? What does she do for a living?” If you’re serious with someone, it’s, “Is she the one? Are you two going to move in together?”

You follow me; and so on, and so forth.

Forget the extra glass of red wine—sometimes families can be a real headache. (Not mine, of course.) So how do you handle Mom’s cousin Shelly and good ‘ol Uncle Jim grilling you about your love life? When is it okay to serve up the pumpkin pie with a side of little white lies?


Last year I effectively dodged all the potent questions about the different guys I was dating. Granted, there may not have been a particular stand-out candidate, but it was still the right move.

Saying too much to your family can sometimes give them too much ammo, too much to bother you about later, and, perhaps most dangerous of all, too much hope.

Family wants you to be with someone. Family wants you to be happy. Family wants you to get married and start your own family. It is your job— and your job alone—to manage those (sometimes crazy) expectations that are particularly heightened during the holidays.

If you’re smart, you’ve done it over time. You’ve slowly leaked the details of the woman you’re wooing (because you are wooing her, right?) as the relationship has progressed. But let’s say you aren’t the call-Mom-and-tell-her-all type.

No time like the present to start: Call your mother. Give her the basic background information so she’s not surprised when the turkey comes out of the oven. This will also give her ample time to fill in the other important characters—cousin Shelly, Uncle Jim—before you arrive home for the holidays next week.


Just like my brother, the quarterback, will assess the opposing defense to decide which play to call, so do you too need to feel out the soup-eaters sitting around your table before you make your move. Sometimes the best plays are the most straightforward. Keep it simple. I told everyone last year I was really happy, meeting a lot of great guys, and having the time of my life. It was one of those “the less said, the better” situations.

Other times the only way to a touchdown is by using a little bit of trickery. Pick your most trustworthy and effective teammate—or relative—and try a wildcat offense. I might tell my sister-in-law the important facts I don’t want the rest of the family to know—at least not yet—and let her quarterback the conversation instead. It’ll take some of the pressure off of you while that person guides the rest of the team to the goal line.


Know who your cheerleaders are, and know who is trying to read your passes. If you fail to identify the latter, in the time it takes to go from the first course of mushroom barley soup to that homemade pumpkin pie for dessert, they will unspool your romantic feelings like a ball of yarn tumbling down a flight of steps.

I’m not saying to always hide your feelings. If you like the woman—and I mean really like the woman—then go ahead and gush. Along with the gravy on the side of your mouth, it’s probably all over your face anyway.

But there is a time and place for everything.

Remember this is powerful stuff you’re sharing; your family will hang on every word. They don’t easily forget, either. Whatever you tell them now, you will surely be hounded about again next month, come Christmas or Chanukkah.

So before you spill your guts at the table next week, ask yourself this: Do I want my pumpkin pie with sugary-sweet vanilla ice cream and love? Or would it be wiser to serve it up with a small side of little white lies?

In two weeks: Jamie’s Holiday Gift Guide