8 TIPS FOR DATING DURING THE HOLIDAY SEASON
HELENA LORIMER
DECEMBER 11, 2024
5 MINS READ
It’s that time of year again! Festive events, office parties, gatherings, Christmas Eve, Christmas, and New Year celebrations.
And let’s not forget about the Northern Hemisphere—those who are cold and looking for a cuffing partner.
All in all, dating over the holidays is hard. Especially when it’s a first date or the beginning of a new relationship. It’s basically a whole new set of rules that apply over this period.
Tiring, yes—but if you follow some of our tips for dating during the holiday season, you may just enter the new year slightly unscathed.
Gift Giving can be tricky. Consider talking about it to make sure everyone is comfortable. Being open about gifts will make a big difference in your relationships. This will prevent any gift giving awkwardness or unwanted stress. Communication is key.
Consider talking about gift expectations early on. If you’re not really ready to have a serious chat about gifts, make it more informal. A simple "Are we exchanging gifts?" can suffice. It opens the door to a comfortable discussion and sets the stage for stress-free gift giving.
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Another great idea is to just go shopping together and get something for one another. That way, you know everyone involved will like their gift. And your best bet may just be deciding to do an activity together, think small concerts, winter fairs.
Equally important is to discuss how much you’re both planning on spending, just so there’s no unevenness. Discussing budgets beforehand ensures that no one feels overwhelmed or undervalued. This prevents any potential awkwardness or financial strain during the gift-giving process.
2. Festive Events & Parties
If you and your new partner have mutual friends, this will be a lot easier, as you’ll probably be invited to the same party or parties.
But what about work events? You know how some office gossip goes. Do you take your new person with you to these kinds of celebrations?
Well, you’re just going to have to be brave enough to actually talk about it. And when you do, it’s best to define where you stand. If it’s a casual dating situation, it would be great for both partners to know beforehand as not to assume anything.
Family events are, of course, way more intense than a mere friend or work group hanging out. If you feel that the relationship you’re in has a future, and both of you are comfortable with this kind of thing, then you can invite them.
Perhaps you’d like to let your family know it’s new beforehand though, just to avoid any intrusive or awkward questions.
If you’ve decided that you and your partner will indeed go to each others’ festive events or parties, think about your outfit.
If you’re going to their work or family event, it’s probably not the best time to show off your most revealing and/or trendy outfit.
There will be many more occasions, with or without your new partner, to wear a sexy outfit.
Outfits to Events & Parties
Intimacy
The honeymoon phase of a relationship is great, largely because it’s filled with exciting and new sex.
But when the festive season comes around, people are busy. End-of-year work deadlines, events, etc. You don’t want to lose the sexual spark too soon, so we suggest making time for intimacy.
Make sure to plan a date or two in advance so that you can enjoy each others’ company… and de-stress.
Sex aside, having an intimate date or two simply to be with each other is a fantastic way to get to know them better and to connect.
It could even prompt the growth of a more meaningful relationship.
5. Going Back to Your Ex
A lot of people tend to reflect at the end of the year. They may realise that they’re actually feeling quite lonely and they may look for solace somewhere familiar… such as with an ex.
This is usually a bad idea. Before you dive in and start texting your ex, ask yourself two questions: have the reasons or circumstances that led to the breakup changed? And would meeting with them lead you to fall into the “short-term gain, long term pain” pit?
The answers to these can help you to decide whether it’s worth the temporary company.
Likewise, “cuffing” up a new partner just because you don’t want to feel lonely for the holidays isn’t good intentions. There is no need to jump the gun on anything new.
6. The Holidays Spent Apart
If you’ve decided that you won’t be doing holiday events and parties together, maybe a little chat about that is a good idea.
For example, deciding whether you’re officially dating, if you’re in an open relationship, or if this is merely a fling and both can do as they fancy.
There’s nothing quite as hurtful as finding out a new interest was intimate with someone else during the Christmas period when you had your sights set on them.
Use this quality time surrounded by friends and family to recenter and figure out what you want for your future – maybe it’s enjoying the next few years traveling while single, and maybe it’s marriage and kids as soon as you meet the right person.
7. New Year’s Eve Date
Are you wondering whether your new love interest is going to ask you to hang out on New Year’s Eve? Well, the general rule of thumb is, if they haven’t asked you by Christmas, the chances are low.
Most people plan their New Year’s Eve celebrations a week or more in advance, so Christmas is a good goal to think about.
If you haven’t heard from them about spending the holiday together and you haven’t asked them, then you should probably go ahead and make your own plans.
Short-Term Relationships
Winter is also a notorious time for engagements, and when surrounded by other relationship milestones, we have to ask ourselves – are the flings worth it?
A study by YouGov found that men are more likely to answer yes to that question, as are Boomers when compared to Millennials.
While those all sound nice, it’s really up to you to decide if you’re ready for a serious partner or if you even want one.
And if you do, an informal chat about things could just be the magic that brings you two closer in the new year. Wishing you tons of holiday fun!
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HELENA LORIMER
Helena is a sex-positive freelance copywriter in her mid 30’s from Cape Town, South Africa. She’s travelled and lived in various countries in Asia and Europe for almost a decade, and continues to live her dream — traveling the world independently as a copywriter. Having written for various companies and magazines within the industry, she has extensive knowledge in the field of sexual health, the escort industry, and sex toy marketing.

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