Should I flirt with my boss at the holiday party — and other festive questions

From family stress to work-party hookups, Claudia Dey helps you navigate the holiday season.

Family with two children (4-6) opening gifts by Christmas tree

Photo, Superstock/Getty Images.

Dear Claudia
My brother and I are really close, and he just told me he has been having an affair and wants to leave his marriage. But first he wants to fly 3,000 miles with his wife and my two beloved nephews to spend one last Christmas as a family — at our house. If I say yes, I’m a complicit liar. If I say no, I’m a terrible sister. What do I do?

Dear Supportive Sibling:
An ongoing affair is like a Sudoku of lying, trying to ensure that the excuses and omissions add up. Your brother is thinking only about the now — not about the future. Still, you probably can’t change his mind. He is going to leave a heartbreaking mess by undoing the structure of his family, regardless of what you say. What must remain intact is your relationship with his boys — and with him.

I know it’s hard being the only one who has a sense of what is to come, but by confessing to you, he is showing that you are the only steady presence in his life. Let him lean on you. And let him have one last perfect holiday. Once his secret life becomes his real and only life, perhaps some good will emerge (a father is much more engaged with his children when he is not doing Sudoku). Try to forget what you know and enjoy the untroubled time you have together for this holiday season.


Dear Claudia,
I’m hosting our office holiday party at my place this year, and I have a serious five-alarm crush on my boss. I know he feels the same way — and that his wife is out of town for the party. I realize how wrong this sounds, but it feels like the perfect chance for something to happen between us.

Dear Boss Crush,
I am throwing a pail of freezing fjord water at you. I’m sorry, but you do need to snap out of it. There is no perfect chance for something to happen between you — until he is unmarried. Surely, you have read the bumper stickers, the graffiti and the Greek myths? The upshot: Stay away from married men, especially if they’re your boss.

And if the married man won’t stay away from you? Husbands who stray have already proven themselves untrustworthy. Let’s say he kisses you at the end of your party — mistletoe, eggnog, the winter sun rising — then leaves your home, perhaps leaves his wife, moves into your home, marries you and then, one day when he is out until dawn, you will wonder: Who is he kissing now? Cheating — just like any form of lying — will haunt you until the end of days.

Instead, come at this crush the right way, the honest way. If it feels like he is the love of your life, wait for his circumstances to change. As it stands, he can always go home to his wife, while you risk having to leave or losing your job. The moral of the story: Until you are both available, you will have to look for your five alarms elsewhere.

Dear Claudia,
I’m 24 and have lived on my own for six years, but I always go home for Christmas — and it’s always a disaster. (My stepfather is a brute.) This year, my new boyfriend has invited me to stay with his family. As tempted as I am, I worry that it’s too much too soon — and, worse, that I will break my mom’s heart. Please help!

Dear All Grown Up,
You must do what is good for you, while still being considerate of others. This is the sometimes overwhelming first instruction on how to be an adult. (No one has yet figured out how this applies to the holiday season, but let’s give it a try.) In your case, you want three things: an un-disastrous Christmas; to pace your romance; and to protect your mom’s heart. What does this worthy wish list look like in action?

Perhaps an attempt to celebrate Christmas with your mom — without the Brute. This might mean inviting her for a sleepover, her favourite dinner and a gift exchange — on a night other than the 25th. You may also want to spend some time with your boyfriend’s family, though it might be best to choose another day. The heavyweight trifecta of the 24th, 25th and 26th might feel too high-pressure — and too “engaged to be married.”

Knowing you’re entering the season with a new format — one that you’ve actually scripted for yourself — might just help you recover your holiday cheer.



Claudia Dey is a novelist, columnist and Governor General’s Award–nominated playwright. She is the author of How to Be a Bush Pilot: A Field Guide to Getting Luckier.

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