There is one question every single person hates being asked at holiday gatherings (but inevitably always is): "Are you seeing anyone?"

Between work functions and holiday mixers, the pressure to be coupled around the holiday season can be disheartening and stressful for singles.

"There are two dates on a single person's calendar they dread the most: Valentine's Day and, ironically, the Christmas season," said Paddi Rice, the president and CEO of B.C.-based Executive Search Dating, a headhunting service for successful singles.

Rice said part of the stress comes from well intentioned family members whose prodding questions can be more annoying than helpful.

"You're getting together with a lot of family and people you haven't seen in a while and you get those old aunties trying to set you up with someone," he told "It can be pretty terrible."

The secrets of "Holidating"

But while the holidays can be a time of dread, it doesn't have to be. Rice said December is actually the easiest time for meeting someone new, a term he coined "Holidating."

"Saying 'Merry Christmas' might be the best pickup line ever - but it only has a shelf life of about three weeks. So why not take it out of the closet?" he said.

"Everyone is in a good mood and open to sharing the holiday spirit."

Toronto-based dating and relationship coach Kateryna Spiwak agrees. She advises her clients, whether age 20 or 70, to take advantage of the holiday season.

"There's a societal expectation that people will spend time with each other, with friends, with a meal and drinks. People are more open to dating because they're already in that mode and interested in socializing."

Spiwak said there are four key points for sparking a new flame during the holidays:

  • Accept all initiations. "You never know who you're going to meet and where you're going to meet them," she said.
  • Create opportunities. "Be proactive. It could be going out to some singles events, group events or going out to speed dating -- anything that you see that may involve a gathering afterwards."
  • Take some risks. You need to push yourself out of your comfort zone a bit.
  • Take action. Something as simple as a wave and a hello is enough.

Debra Fine, the Denver-based author of The Fine Art of Small Talk, says the most important part of Holidating is taking the initiative.

"It's just a matter of being the first person to say hello," she told from her Colo. office.

"Lets face it, there is no perfect icebreaker."

Fine says asking relaxed, holiday-themed questions at parties are a good way to break the ice -- without the pressure.

"Asking about family traditions, plans for the season, what their favourite gift would be. These are all really easy ways to get into a conversation. And relax. This is a great time of year for meeting someone."

But don't go too fast...

Spiwak said even though the merriness of the holiday may accelerate the dating process, it's still a good idea to keep your guard up.

"Sometimes people are feeling a little bit lonely and a bit vulnerable and might get together with someone they might normally not."

She advises singles not to drink too much on their dates or rush into anything too quickly, including introducing them to your parents.

"And if you've just met someone it is absolutely inappropriate. You could end up looking desperate and that's the last thing anyone wants."