Your Guide to Dating During the Holidays

Your Guide to Dating During the Holidays

Posted By: Kelly Seal Date: 12-01-2018 Comments: 0

The holidays are here! If you’ve just started dating someone new and aren’t sure what to do this holiday season, relax – we’ve got you covered.

We’ve taken our top 5 of those tricky topics – like whether or not to buy your new love interest a present or invite him over for your family’s holiday dinner – and given you some time-tested advice. Now is not the time to sweat the small stuff. Save yourself the stress and check out our handy Q&A guide to dating during the holidays…

We just started dating. Should I invite him/her to my holiday office party?

If you’ve only been on a few dates and are still feeling the relationship out, hold off on inviting your date to important events, like meeting your work colleagues. While it might seem fun to have a plus one, invite a pal instead of a date to take the stress off of both of you – there’s plenty of time down the line to enjoy a work-related happy hour together!

If you’ve been dating for a bit longer and feel more comfortable around each other, AND you think the relationship has future potential, then inviting your date to meet your colleagues is up to you. Think about the venue first and whether your date will be comfortable, too – is it a casual gathering at a bar or an event with dinner or fancy dress codes? How many people will be there? How much will you and your date be drinking? It’s important to know these things – after all, these are people you work with every day. If inviting your date feels like too much pressure, better to wait it out until after the holidays.

What kind of gift do I buy for someone I’ve only been dating a few weeks? Do I get a gift at all?

The rule for gift buying is simple: if you haven’t been dating for very long, then don’t expect a gift. There’s no need to go crazy on holiday gift-buying for someone you’re still getting to know, especially because it could make your date feel awkward. Imagine you’ve been dating a few weeks and your date gives you a lavish gift like a diamond necklace – is that an indication your relationship is more serious than you thought? Do you feel more pressured to give him an expensive gift?

Instead of stressing over whether to buy a gift, and how much money to spend, relax. I would suggest getting a small gift to acknowledge your date, especially if you’re worried he will get something for you and you don’t want to show up empty-handed. Try a more generic gift, like a bottle of scotch or wine, or a book by an author he likes, or an assortment of coffee beans if that’s his thing. If there’s an event coming up you think he might enjoy, buy a couple of tickets if it’s in your price range. This shows you’re thoughtful without the stress of spending too much money.

Should I introduce my new love to my family over the holidays?

Maybe you’re crazy in love already, or maybe you are taking things slowly and seeing how your relationship evolves. Regardless, I would caution against introducing your new love interest to your family over the holidays unless you’ve been dating a while and are more serious about your relationship.

Family time around the holidays is limited, and events and social gatherings are usually steeped in tradition. If you are unsure if your date will fit into the picture long-term, why go through the stress of including them in your holiday celebration? Let’s face it – when you invite someone home with you for the holidays to meet your family, it implies the relationship is serious. If you aren’t quite there yet, and especially if you haven’t had the conversation about being exclusive – why put yourself and your family through the stress? Wait until after the holidays to make introductions, when you and your date feel more comfortable and have discussed taking this next step.

Should I take a break from dating until after the New Year?

No way – the holidays are the best time to meet someone new! There are a ton of holiday parties and chances to meet new people in social settings instead of just over an app, giving you an advantage to actually ask someone out. Say yes to invitations and get outside of your comfort zone. It’s okay to go alone to a party, or if you feel more comfortable, grab a friend to be your wingman/woman. This is a great time of year for dating – plus, the winter can be very romantic. Go for it and have fun!

What if my date doesn’t invite me to her holiday parties, even after I’ve invited her to mine?

If you’ve already invited your date to a holiday party and she hasn’t returned the favor, don’t feel embarrassed or frustrated. It doesn’t mean that your date isn’t interested, it’s just that you have different comfort levels with introducing your date to the people who occupy other parts of your life – whether it’s friends, co-workers or family.

Instead of second-guessing your next move, try just having fun and getting to know your date better over the holidays. Approach the season lightly when it comes to dating – again, take the pressure off of both of you.

In addition to inviting her to a party, plan dates for just the two of you. Ask her what she enjoys most about the holidays – the lights, cooking together, whatever – and make plans to do it. And if she seems distant, ambivalent, or puts you on hold? That’s no reason to spoil your holiday. Maybe it’s time to move on, so enjoy your friends and family and try dating someone new.

Happy holiday dating!

Kelly Seal is a freelance writer, dating expert, and author of the book “Date Expectations: A Guide to Changing Your Dating Life and Finding Real Love.” She got her start in the dating industry by hosting speed dating events around southern California and offering advice and encouragement to attendees. She now lives in L.A. and spends her free time hiking in the Santa Monica mountains and blogging at