5 Tips For Flirting At The Office Holiday Party

It's time for you office's annual holiday bash and you've got a crush on a coworker. How should you handle it? We'll help you negotiate the tricky aspects of flirting on the job.

By Dave Singleton

"I had my eye on a hot colleague at our company holiday party, but didn't have a clue what to do," said Washingtonian Linda, 29. "He was so sexy and smiled at me. I felt an intense attraction, but bosses and colleagues were everywhere I looked. So I just let the moment pass and did nothing."

The holiday party can't be all about drinking eggnog (ugh, who thought that up?), talking to the third-floor chatty Cathy, or hanging with your coworker's lonely, bored wife all
I felt an intense attraction, but bosses and colleagues were everywhere I looked.
night. You want to have fun with colleagues, make a few smart (and sober) professional connections, and — if you're lucky — spice it up with a little romance, too. But what if you see Mr. Hottie across the ribbon-festooned table as you gobble one of those powdery white Russian tea cakes that bakeries only seem to make in December? What then?

If you meet someone at a holiday party — where there's an even ratio of work colleagues to "inhibitions out the window" behavior — there's a lot at stake. Any time you're enjoying the company of your company, so to speak, it pays to be careful. Especially when mistletoe and festive drinks are encouraging you to let go, remember that other eyes are watching you and your professional reputation is on the line.

It may be challenging, but don't despair — there are ways to successfully pursue and start dating someone that you meet through a company holiday party or event. Just remember to follow these five guidelines to safely cross the bridge from work to romance:

1. Make it your policy to know your company's HR policies.
Businesses have cultures, and cultures vary from buttoned-up to liberal. While some workplaces are open to office romances, others may not be. Before you allow yourself that first magical holiday flirt, make sure you know what the rules are. Forewarned is forearmed. Does your company's policy specifically forbid office romance? If so, you may have to ask yourself if a hot holiday crush is really worth losing your job over. If there's no anti-office romance policy, you still need to assess company culture and determine if a romance — assuming you are both discreet and respectful during company time and on company property — could work.

2. Prepare yourself for the three disastrous "Ds" of office parties beforehand.
Before you step into the corporate holiday wonderland, ask yourself if you're prepared to manage the three disastrous "Ds" of such office parties: namely, drinks, dancing and desperation. The three Ds can take down professionals faster than a stomach virus, and with equally unpleasant consequences. Make sure you:
  • Drink judiciously. It's not hard to hit it off with a holiday crush at an open bar, especially if you're single in December. But there's a fine line between getting his or her attention and drawing attention to yourself, and that line gets finer with each drink that finds its way into your hand.
  • Dance like everyone's watching. Whatever you do, avoid being the "dirty dancing" show-off who shakes, shimmies and hurls yourself at that sexy coworker from Accounts Payable.
  • Ditch the desperate vibes. Uninterested singles can sense desperation like a dog senses fear. If you've chatted someone up and the other person's not picking up on your signals, don't take that as a cue for you to work harder. Walk away instead.
3. Network your way into a date.
'Tis the season of giving, and by giving, I mean offering up your undivided attention, suggestions for activities outside of work, and business cards (you brought some, didn't you?) — not your reputation. Treat your
Whatever you do, avoid being the "dirty dancing" show-off.
office party like a networking event, not like last call at the only bar in town. Look for ways to make a connection that might lead to a future plan with Mr. or Ms. Right, who happens to be standing right next to your boss. Treat the food, drink and entertainment options as opportunities to snag some one-on-one time. Bring up topics that tie into activities that will lead the conversation towards talk of a concert, restaurant, sports event or movie you might want to see together in the future.

4. Proceed with caution and keep your expectations in check.
You've made a list and checked it twice, like the good holiday dater you are. At the top of your list is that attractive person from Marketing… but your paths never cross during the work day. That's the situation Marylander Ali, 27, found herself in as she prepped for her company's office shindig. "For months, I'd dreamed about seeing Josh at the party. Hanging out in a social setting would be perfect, I thought — and then I'll find out if he likes me," she says. Talk about high expectations! The party might just be about igniting a slow burn, as opposed to a fast flame. Think about how long it took for enamored colleagues Jim and Pam from The Office to finally get together. Don't get discouraged if you get mixed signals or a reserved response at the event. Remember, the other person is probably just as wary about acting like a fool at the party, too. But make contact so it's easier to chat the next time you see each other in the hall at work.

5. Keep your crush to yourself.
What's the first thing you'll want to do when eye contact with your business colleague seems to be working? Tell someone, of course! But remember, these folks don't qualify as your best friends. If you want to guarantee that "all is calm, all is bright" during your holiday party, then make it a silent night — at least when it comes to sharing your excitement with others. Many a work romance has gone up in smoke once the office gossip gets wind of it. And while gossip can be evil, it's also no joke. Cautious PR tactics can prevent a social media disaster, too. Know that what you say (or, worse, are photographed doing at this event) could end up under someone's online updates without your knowledge.

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