Managing The Holiday Trifecta

Christmas, New Year’s Eve and Valentine’s Day: ‘Tis the season to stress about being single! Try these tips for managing the toughest two months of the year.

By Dave Singleton

t’s that time of year again. The time between Christmas and Valentine’s Day is joyous for some. But for many singles, it’s what I like to refer to as the trifecta of overwrought expectations.

Christmas, New Year’s Eve, and Valentine’s Day fall within two months, and those 60 days can feel like years. Especially when you factor in the specters of kiss-less mistletoe, a dateless chorus of “Auld Lang
You are under no obligation to spill your guts with details.
Syne” and no valentine of your own — it’s definitely enough to make you dread being single.

No relationship to tout when you go home for Christmas? Your relatives will smell it on you like fear on a dog, so you better ready a fast response to avoid a long and potentially uncomfortable conversation.

No date (besides Ryan Seacrest on your new Sony plasma TV) for New Year’s Eve? You can always rely on delivery people to bring dinner for one, assuring you won’t be totally alone.

No loving boyfriend to help you ignore the seemingly endless parade of happy couples on Valentine’s Day? Take a jealousy management class so you’ll feel less like an envious “dating Scrooge” every time you pass a couple holding hands. Yes, it’s true: ‘Tis the season when your singledom is painfully obvious to you and everyone else, too. So how can you stop your holidays from becoming a sad holi-daze? Follow these five strategies to keep your spirits strong:

1. The best defense is a good offense
“Spending the holidays unattached can be disheartening if you’re deluged with ‘Why are you still single?’ questions from relatives or notice romance swirling in the air around you, but realize you’re missing out,” says Kimberly Dawn Neumann, founder of and author of The Real Reasons Men Commit. Armed with the knowledge that this could be a tough season, start mentally preparing for inevitable lonely times and questions that come during the holiday trifecta. For example, plan a response now to your family and friends’ questions about your former partner. Just a simple statement that it didn’t work out should do, and then quickly change the subject. You are under no obligation to spill your guts with details.

2. Network your way through the trifecta
Socializing with the right attitude could serve you well over the next few weeks. “The trick is not to focus on your lack of a partner but, instead, to use this season to have fun with friends and perhaps subtly network your way into finding dates,” says Neumann. “Attend all parties to which you’re invited and partake in holiday outings like ice skating or caroling. You never know if one of those outings will lead you to finding a match during this wintery time of year.”

Remember that you’re not alone in these situations. Many others may also be feeling the holiday trifecta blues. So treat social events as opportunities to connect with friends, old and new, rather than desperate attempts to score your next Mr. Right. While there’s no guarantee that you’ll meet your next partner, you’ll have fun making new friends and connecting with people in the same boat.

3. Avoid treating the holiday trifecta like a race
Some single people look at Christmas as the starting gun and Valentine’s Day as the finish line. I want a boyfriend now, so I am going to get one ASAP! Despite the pressure you feel to cure your singledom with an instantly materializing new love,
You should use this time to regenerate and recharge.
remember that this time period is not a race. Counting on Cupid’s arrow to land on Mr. Right sometime between December 25th and midnight on February 13th puts too much pressure on you!

Make an early New Year’s resolution to only set timelines for things you can control. For example, instead of setting an overreaching goal such as, “I want a boyfriend by Valentine’s Day,” how about a more reasonable ambition? The best goal might be, “I will commit to activities that make me feel better about my love life than I do today.” You can set goals such as attending networking events and parties, as well as sending out online dating feelers. You can review weekly the actionable steps above to quantifiably gauge your progress.

4. Only date if you can keep your expectations in check
Advertisers love creating images of couples enjoying perfect “Hallmark-style” holidays. But the expectations they help set create a perfect storm of despair. How can your normal holiday not pale in comparison to what’s depicted in the media? Since the pressure (and desire) to be coupled is heightened during this two-month trifecta, be extra careful about dating during this time. I wouldn’t hold to a hard-and-fast rule like, “I won’t date anyone until February 15th.” But go out with someone new only if you’re able to a) feel good about yourself, b) keep your sense of humor, and c) approach the new guy with your expectations in check. If you feel joyless, angry, sad, or overly needy, stick to hanging around your closest friends until you feel better.

This time of year can be a good time for excess (think Christmas cookies, New Year’s toasts, and Valentine’s chocolates). But when it comes to dating expectations, limit your intake.

5. Start planning your New Year now
Some experts suggest that, in addition to socializing, you should use this time to regenerate and recharge. “The time between Christmas and Valentine’s Day is a great time to celebrate your single status,” says Cherie Burbach, author of At the Coffee Shop and Internet Dating is Not Like Ordering a Pizza. “Be good to yourself and do all those things you can’t when you’re in a relationship. Make whatever you want for dinner, hog the covers, read all day, and make plans for a new year filled with whatever makes you happy!”

Consider, too, what kind of partner you might want in the future. Are your standards reasonable? What activities do you want to pursue and possibly share? What friends and events are conducive to meeting a new Mr. Right? Look at this time as pre-spring training before you enter your post-trifecta dating season.

Dave Singleton, an award-winning writer and columnist for since 2003, is the author of two books on dating and relationships. Visit Dave’s website and send your dating questions and comments to him at
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