TCW - Dating During the Holidays

Is Dating in December futile or fruitful?

Contrary to popular belief, dating during the holidays can be fun and fruitful. I get a lot of holiday related questions, and thought I’d address the two main ones:

Dating in December – Futile or Fruitful?

Last week, during a lunchtime coaching session on Michigan Avenue, one of my lovely Chicago clients asked me if I believe that men “go on dating hiatus, and shut down and hibernate between December and Valentine’s Day.”

The answer is a resounding “no!” If you’ve been reading my columns for the past few months, you know that there are good men everywhere and at all times (especially now!). Think about it: the Christmas holidays are when people are out and about, dressed up and ready to mingle. Your challenge is getting yourself into situations/being available to meet them. All year long, people complain about not wanting to meet men in bars, not getting set up, not having parties to go to.

And now, think about your December calendar. Many of you have weekends that are double and triple booked with parties – hosted by friends, colleagues or family members. Keeping in mind that 1/3 of married people were introduced by family or friends, what should you do when you’re invited to a party? Say yes to everything (or as many as you can humanly handle). Enter with your flirty, friendly, approachable face (smiling, eye contact), and have some icebreaker questions in your pocket ready to fire out at the cute boy by the fondue fountain

And for you gals in relationships going to the parties, don’t forget about your single friends. Play the matchmaker. Keep your eyes open for your single friends at the holiday parties. Get the emails/numbers of interesting guys – and bring yourself some good karma.

What should I give my new squeeze for Christmas?

The eternally stressful situation – I have many clients in this boat. They’ve been on 5-10 dates with someone, and are very close to being “off the market.” My advice is if you’re in a newly budding relationship, go high on the thoughtfulness but low on the budget. Think of something that they've talked about being interested in/liked/wanted to do, then think of a fun gift along those lines. I once went on a first date in December with a guy who was a great listener. I told him that I loved French Impressionism and that Monet's "Two Sisters" painting was my favorite. The night after our date (near Christmas), he dropped off a box of Renoir note cards with my doorman, with a note on top that said, “Had a great time today!” Did he get the second date? Absolutely.

One of my NYC clients and her new beau (they’ve been on eight dates) both love cartoons, and he especially loves the Tasmanian Devil. She searched high and low to find a Pez dispenser with Taz’s head on it – and has made him a “gift certificate” to spend any night of his choice on the couch watching the Cartoon Network with cartons of his favorite MidTown Chinese food. Keeping high on thoughtfulness shows the person you listen and care about them – and will earn you big brownie points.

So, get your sparkly, pretty clothes ready for the next few weeks – and say yes to everything you get invited to. Be the fun, smart girl you are, put on a happy face, an icebreaker in your handbag – and you’ll be the belle of the ball