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IJL Team Member Cassie

Dating During the Holidays? Tips for Handling a New Romance


‘Tis the season for those frantic internet searches, like “how much should I spend on a romantic gift” or “how long should I date someone before I can ask them to my office holiday party”. We understand that the holidays are stressful enough without adding dating into the gingerbread mixing bowl. So, we’ve gathered some of our Matchmaker’s favorite tips for navigating through a new romance this time of year.

The Art of Gift Giving:

Stop over-thinking the question “to give or not to give,” and go with the spirit of the season. The key is to talk about it. Yes, it can be slightly awkward to bring up, but it’s less awkward than not having a gift for someone you care about if they have one for you. Your conversation can be as simple as “are we exchanging gifts this year?” If so…

  • Consider giving a hobby-themed gift. It sends a thoughtful message that you know them, and you’ve been listening to what they’re excited about.

  • One of our favorite gift ideas is a shared experience. It says to the person that you’re with that you are hopeful for the future. It's also something fun for the two of you to look forward to.

  • A very safe option for new couples is a game. There is no personal attachment to it and you can play it together, which is also a great dating idea.

Home for the holidays!

  • As a rule of thumb, you may want to ask yourself: if it wasn’t for the holiday season, would I be inviting my new partner to come home and meet my family right now? If the answer is no, it’s best to celebrate separately this year. Besides, when your new romance lasts until after the wrapping paper is tossed and the tinsel is put away, you will have many more holidays together with your family.

  • If you do decide to spend the holidays together with their family, make sure you don’t show up on their doorstep empty-handed. Consider picking up a beautiful bouquet of flowers or a nice bottle of wine as a gift of appreciation for welcoming you into their celebration.

Beside family gatherings, the holidays usually bring office parties with co-workers and clients.

  • Don’t get discouraged if your new partner doesn’t invite you to their office holiday party. You deserve their full and undivided attention, so inviting you to a party where that requires them to split their attention between you, colleagues and even clients, may not be the way they want to charm you.

  • If they do decide to extend an invitation and you choose to attend, make sure to relax and be yourself… and avoid consuming too many alcoholic beverages. You don’t want to be the topic of conversation at the water cooler come Monday.

Whether you decide to exchange gifts, invite them to your office holiday party, or spend the holiday together with your family, make sure to make time for romance and perhaps start some new holiday traditions together. Putting stress aside, the holidays are a wonderful and magical time of year. We recommend you take advantage of the extra romance in the air and all of the wonderful date ideas that the holiday season brings.

Whether you’ve been together for years or weeks, any relationship can become stressful during the holidays. There is no recipe or measurements to follow. Communicating with your partner is key to having a warm and wonderful holiday season.

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