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.

Last week he told me he had a surprise for me. When he said he would give it to me the following day, I asked for a clue. 

After moments of pondering he said, “Something we’re going to fight over.”

Something we’re going to fight over? I thought. I stared into his eyes like a police officer would during an interrogation, waiting for a confession from the culprit. It didn’t take me long to read the grin on his face and realize what he meant; the present would involve competition.

Bag in hand, he came over the next day, as promised, to deliver the surprise—first a card, and then my very own ping-pong paddle.


Gift giving can be fun and even momentous at times, but it sure isn’t easy. He nailed it last week though. The card was thoughtful, the present meaningful— we play ping-pong together a lot—and the surprise element elevated the whole occasion.

Just as this guy wanted to show his gratitude, the gift you buy for your woman this holiday season depends on the message you want to send. Yes, every gift—even no gift—sends a message. So what do you get her? Maybe you want to spoil her, but you don’t have a lot of money. Or perhaps you’re into her, but don’t want her to think you want a serious relationship. There is an appropriate present for every phase of dating, each of which includes a well-written card.


If you’re at least thinking as far ahead as New Year’s plans with this woman, then you should buy her a gift. You don’t have to go overboard, but a little something goes a long way, especially if you’re hoping to kiss her when the clock strikes midnight on January 1.

If you’re not monogamous (and aren’t trying to be), avoid a wrapped present, which might be misconstrued as a plea for that status. Instead, plan a fun night out, like to dinner and a concert. Doing something together is always the best kind of gift. If you don’t have the dough to shell out for tickets, invite her over to your place and cook her dinner. Plan a menu full of her favorite foods and most importantly, make sure to have her favorite liquor on hand. Flowers and candles are a nice touch, too.


If things are a little more serious, and you’re hoping she’ll be your Valentine on February 14, then break out the wrapping paper and bow. Think about what you’ve done together, places you’ve been, jokes you’ve shared, and stories she’s told. Perhaps she’s been complaining about how old her watch is; get her a new one. Maybe she’s been dying to go to an Eagles game; buy tickets and take her.

I wouldn’t buy her clothes or something household-related. Unless you know (because she has explicitly told you to get the black coat in a size 4), judging your woman’s clothing size can be detrimental to your relationship. Likewise for any tool or gadget for her apartment; leave the screwdriver and TV stand for her dad.

Instead splurge for new sunglasses, a bag or wallet she’s been eyeing, or iPad, iPod or Kindle. 


A little more time and care are required if she's your girlfriend and you want to make fireworks with her on the Fourth of July. A woman wants to know you thought about the gift, that you spent time figuring out what would make her happy. If your bank account allows, a weekend away at a bed and breakfast is special. Not only are you taking care of the details (women love a guy who makes plans!) but you’re also telling her you want to spend time with her.

Not every woman wants (or can have) a cat or a dog, but a different kind of small pet could be cute. I once gave a guy twin tree frogs as a present. Roll your eyes, but it was unique and memorable, plus it was a chance for us to care for something together.

A special piece of jewelry is always an easy go-to, but make sure to consult with her best friend or someone who knows her well before buying.

This is your chance to really win her, so give her clues and make it exciting. Send her a riddle via email once a week until Christmas or Chanukkah and let her mind swirl with possibilities.

If you’re worried about your wallet, bear this in mind: no blow-out present is going to make up for bad behavior, nor will it ever take the place of day-to-day chivalry and hand-holding.


Don’t forget the card. A woman will always remember a guy who writes her a thoughtful note. It doesn’t have to be a love letter, just short, sweet and from the heart. The guy who gave me the ping-pong paddle wrote two simple sentences in his card: an inside joke between us first, followed by the two most important words a man can say to a woman.

“Thank you,” he wrote, and signed his name.

I loved that; he is thankful for me. I was just thankful he didn’t sign his name with a heart.

Next Week: Is she holiday party-worthy?