How to Handle Awkward Holiday Moments

Ah, the holiday season. It’s a time when we connect with friends and loved ones we haven’t seen since last year…your brother who lives in California, your childhood bestie who comes back to town, your drunk uncle and of course the awkward turtle. Ok, the last two may not be towards the top of your nice list, but nonetheless, the holidays bring them out in rarer form than usual (which says a lot). Sometimes it seems like awkward holiday moments are the reason for the season and you really wish it wasn’t like that.

There’s not much I can do to get rid of your uncle, sorry. I can help you keep the turtle inside its shell, though. That’s not to say cringe-worthy stuff won’t happen, it will, but it’s how you handle it that counts. To help you make it through the season without turning redder than Rudolph’s nose, I got April Masini, relationship expert and founder of, to share tips on how to navigate the most awkward holiday moments.

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You spilled wine on your SO’s mother’s couch. The wine is red. The couch is white.

You brought over a fabulous dip that everyone is raving about. You complimented your SO’s mother’s dress. You think you’re about to be canonized by your main squeeze’s family…and then it happens. You spill your glass of red all over her couch…and it’s white. Don’t run to the bathroom and cry. First, apologize immediately. “Offer to reimburse her whatever cleaning she needs to have and switch to white wine,” Masini said. It doesn’t end there, though. “Call her the following week to apologize again,” Masini said. “The red wine stain will be there, so it’s a good idea to make that second apology.”

Your parents want to know when you and your long-term beau are getting married and they’re not afraid to ask.


These days, it seems like the only excuse your parents need to ask you when you and your long-term significant other are tying the knot is, “Can you please pass the mashed potatoes?” I’m not sure how spuds make them think of marriage either. “The truth is, they’re asking because they’re concerned about your future and think marriage is the answer to their concerns, they’re old-school and think marriage is a goal to be achieved or they’re bored and unhappy in their own lives and projecting their discomfort onto you,” Masini said.

If they have a habit of popping the question, call them in advance of the party and politely ask them to lay off. Tell them it makes you feel a bit anxious when they ask. Should the question come up, Masini recommends simply saying that you don’t know but will let them know when you do.

You recently became unemployed and it’s your turn to tell everyone what you’re up to.

Dealing with this awkward holiday moment might feel like ripping off a Band-Aid, especially if you were laid off or left your previous gig on bad terms. “If you don’t want to get into it, ‘I’m in transition,’ is very decipherable code for unemployment.”

Another option is to be straightforward. “You can simply say, ‘I’m out of work right now, but I’d love to hear about what you’re doing.’ and if you want, ‘Do you have any pointers for me?'” Who knows, the person may have the perfect connection or lead for you, which would be the ultimate gift.

Your co-worker comes up to you with a gift and a huge smile. You didn’t get her anything. You actually kind of forgot she existed. Ooops.


When you were a kid, the old cliché of “it’s better to give than to receive” seemed like a big load of…coal, but you realize just how wrong you were when someone presents you with a gift and you have nothing to give them. When you’re stuck in this unenviable situation, acknowledge the elephant in the room right away—and be real about it. Thank them and apologize. “It’s easy to get caught up in your own feelings of failure and ignore the fact that someone just spent a lot of time, energy and money on a special gift. Not thanking them because you’re focused on yourself creates a second problem.” Finally, cure the problem within the next week by getting them a make-up present with a card. “Acknowledge what you’ve learned from them, and how you were remiss to overlook their kindness.”

Your uncle is drunk. And he’s teaching your kids new words.

Provided it’s just a holiday-party habit and there’s not a serious problem involved, a tipsy relative can be a riot until everyone starts having children. “Prepare your kids in advance. Letting them in on the problem gives them power to take care of themselves and not feel victimized.”

What you tell your child depends on the age. For a 5-year-old, Masini suggests saying, “Uncle Tony gets really silly at the holidays sometimes. Should we give him a timeout if he says something really inappropriate?”

You can get more specific with a teenage child and even use it as a teaching tool. “You might say something like, ‘you know Uncle Tony sometimes says inappropriate things when he drinks too much. I wish he wouldn’t and I hope he doesn’t hurt anyone’s feelings, but I just wanted to talk to you about this before we go. His behavior when he drinks isn’t something I like.’ This also opens the discussion for teenage drinking either in the moment or in the future.”

Call him before the party to voice your concerns. “Ask if he can cut back when the kids are around because his comments are inappropriate for them.” If he refuses and you’re concerned about the example it’s setting for your children, consider not bringing them or declining the invite.

beth ann clyde

beth ann clyde

Beth Ann Clyde is a Digital Editor of Long Island Pulse. Have a story idea or just want to say hello? Email or reach out on Twitter @BAClyde.