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Holidays with your new guy don’t have to be awkward

If you’re coming off a divorce and this is your first holiday season single, it can be an incredibly challenging time. If you’ve got a new guy, old traditions and family gatherings can feel awkward. But they don’t have to.

Woman and her boyfriend on Christmas

Here are a few tricks to surviving the holidays with your new boyfriend.

Family get-togethers

About this columnist:

You know how one minute you’re in a happy and fulfilling marriage and the next you find out that your husband of 20 years has been cheating on you with someone 10 years younger? Well I do. I went from country club wife and mother of high school students to a single, 39-year-old “cougar.” In this weekly feature, I will share with you all the mind-boggling, head-scratching, is-this-someone’s-idea-of-a-joke moments from my so-called single life. Consider this your private invitation to my tremendous learning curve…

If you just started dating, holiday get-togethers can be a fright. Your mother and aunt will be in the corner wink-wink-nudge-nudging each other over your new man. Your dad might ignore your new date or worse yet engage in that primal tug-of-war where male egos rest in the middle. If the very thought of introducing your new guy to your family gives you the hives, then don’t. Politely explain to your new beau that you have to spend time with your family, but want to spend time with him when the festivities are over. If he does decide to participate in your holiday family gathering, encourage him to bring food that reminds him of his family holidays. If you join him, bring a favorite fail-safe dish and try to relax. Or you could blow off everyone and just go bowling!


Probably the only thing more stressful than the idea of inviting someone new to a traditional holiday gathering is trying to figure out what to get the new love in your life. How much do you spend? When will you exchange gifts? Will he reciprocate? If it’s your first holiday season together, don’t put too much pressure on yourself. Dismiss the idea of impressing him. Go with something creative and from the heart but not too sappy. Early on in relationships, you are sharing a lot of memories and what your favorite things are. Log these away. If he talks about how he misses his grandma’s apple pie, ask him what he misses about it and try to replicate it. Keep it simple, thoughtful and affordable. You never want to set the bar too high early on and paint yourself in a corner next year.


If you’re newly divorced and have kids, it can feel like your heart is being ripped out during the holidays. For the first time ever you may have to spend the holidays without your kids. If that’s the case, thank your Christmas stars that you have a new guy to distract you, because he will keep you from eating a gallon of ice cream in one sitting, and consuming a case of wine by yourself. If you do have your kids and your new man for the holidays, it may be best for the kids and your sake to break things up. The kids will be looking to you to comfort them with traditions from the past, as well as maybe starting a couple of new ones. Perhaps spend the holiday morning together and invite your guy over in the evening for a quieter celebration, when the kids are tired.

The Christmas party

Bringing your new fella to the company Christmas party can be as daunting as a family get-together. You may have dated someone (or several someones) from your office. That can be tricky to navigate. You may not want your coworkers to needle you the day after the party with a barrage of questions. There is a really simple way around all this potential awkwardness. Just introduce your new guy by his first name. That’s it. “This is Joe.” No need for labels. You don’t have to say “This is my friend Joe” (which may insult Joe) or “This is my new boyfriend Joe” (which may get tongues wagging) or “This is the guy I’m trying to decide if I want to keep dating after the holidays, Joe.” Keep it simple.

Keeping it simple applies to all aspects of the holiday season as it pertains to a new relationship. Don’t over-think things. If you’re spending a lot of time stressing over a situation, then get rid of the situation. Just don’t go. There’s always next year. Above all, take care of yourself and your kids and remember if you are struggling that the New Year is just a couple of quick weeks away.

More from Miss B. Haved

When is it OK to have dinner with a married man?
When the adult sleepover has consequences
Attracting men just got a whole lot easier

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