Wintering Together: Preparing for Your First Holiday Season as a Couple
- Date Night Notes
- Dec 8, 2023
- 3 min read

The winter holidays! A time for warm sweaters, hot cocoa, sparkling lights, and...meeting the family? If this is your first winter holiday season as a couple, it’s both an exciting and potentially nerve-wracking time. Navigating family traditions, gift-giving, and maybe some unforeseen mistletoe encounters can be a bit tricky. But don't worry! We’re here to help guide you through this snowy minefield.
Embracing the Festivities as a New Pair
1. Open Communication: Discuss your holiday expectations. Whether it’s attending five family dinners or simply binge-watching holiday movies together, knowing each other's vision will help you to align your plans.
2. Balance is Key: It might be tricky dividing time between two families or sets of friends. Give yourselves time to communicate openly about what's important to you both, and then prioritize events to ensure both of you feel represented in the festivities.
3. Gift-Giving Guidelines: To avoid potential awkwardness, set some guidelines. Decide on a budget or perhaps even theme your gifts for added fun!
Pro Tip: When buying gifts, make sure to keep the individual's personal interests, preferences, and needs in mind.

4. Meet the Family Prep: Meeting the family can be a significant step. Share some family stories or quirks beforehand so there are fewer surprises and more understanding. If you have a close friend or family member who has a history of being challenging or confrontational during gatherings, make sure to let your partner know ahead of time.
5. Create New Traditions: While you’re both used to your own traditions, start something new that’s unique to your duo. It could be anything from making a special dessert to an annual holiday photo or Christmas tree ornament.
6. Stay Flexible: Plans might change. Uncle Mike might have one too many eggnogs. Stay adaptable, and remember, the season is about joy and togetherness.
7. Private Time: In the middle of the whirlwind of activities, find moments for just the two of you. A quiet evening together at home or a winter walk can provide a welcome escape from the holiday madness.
Pro Tip: Make sure that you don't lose yourselves in the chaos of catering to friends and family. Remember that you are still dating (whether you're in a new relationship or 20 years into marriage). Keep dating and be intentional about having fun together...just the two of you...during the holidays.
Navigating Potential "Awkward" Moments

1. Dietary Differences: If one of you is vegetarian or has food allergies, communicate this ahead of time to avoid dinner table awkwardness.
Pro Tip: Nobody makes mac n cheese like your grandmother. Handle food that tastes less than great with grace. Appreciate the effort and the love that went into making the dish, eat as much as you can manage, then cover your plate politely with a napkin to indicate that you are finished.
2. Cultural Sensitivities: Different backgrounds can mean different traditions. Educate each other and your families if needed, promoting understanding and respect.
3. Handling Sensitive Topics: Talk beforehand about any sensitive topics that are likely to come up during casual conversations with family and friends. In between jobs? Differing political views? Undefined relationship status? Discuss how you want to handle those questions so that you can be prepared, be in sync, and have each other's backs.

4. The Ex Factor: Past relationships might come up, especially if there are shared children or events. Discuss comfort levels and boundaries ahead of time.
5. Fitting In: If you are having trouble adjusting to your partner's family or friend dynamic, try making yourself helpful and or available to assist with meal prep or cleanup. Appreciation can go a long way toward opening doors socially.
6. Dealing with Crowds as an Introvert: If you are an introvert, being around crowds for extended periods of time can take a toll and leave you in need of a recharge. It's okay to step away for a quick moment to catch your breath and clear your mind. Just make sure to clearly communicate your needs to your partner and then "take a quick phone call" outside.
Savoring the Season
Above all, remember why you're celebrating together. It's about love, connection, and making memories. So, even if the turkey gets burnt or the tree leans a little to the left, at the heart of it, it's the shared laughter and warmth that will make your first holiday season together unforgettable.
Warm Up with More Relationship Insights
The season might be chilly, but navigating the world of love doesn't have to be. Warm up with Date Night Notes as we serve you heartwarming stories, advice, and the secrets to keeping the flame alive all winter long. Join the community today, and let's cozy up to this adventure together.
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