Getting Into A New Relationship Before The Holidays Is The Most Awkward Thing Ever

Getting Into A New Relationship Before The Holidays Is The Most Awkward Thing Ever ©iStock/Katie_Martynova

There’s never an ideal time to get into a relationship, but certain times of year can be a little less convenient than others. When you start dating in the fall and things are brand new, you enter holiday mode with awkward questions about the events and cutesy sentiments that typically go hand in hand with that time of year. Sure, things are new and exciting, but you can probably determine the long-term potential by asking yourself a few questions.

  1. Do I buy him a gift? It probably wasn’t originally in your budget, but now you’re stressing about if gifting between you two will be an actual thing. It’s a good idea to ask in this case, because it can set the tone of what to expect overall around the festivities. This is step one.
  2. What kind of gift should I get him? What does he even like? You don’t want to get something too overboard, but you don’t want to be too frugal, either. Underwear could be too personal, but a watch could be too much. Gifting the person you’re dating for the first time is a little nerve-racking and it sets the pace of what will be expected going forward. Also, you don’t want your gift to creep him out or scare him off either. Ah!
  3. Should we set a budget? Is that weird? After you obsess about the ideas of gifts, you decide a budget is the most reasonable solution to your problem, which only actually complicates the process even more because finding something within your desired price range is an even more narrowed search. The pressure is on!
  4. Ugh, I actually have to buy the gift. Stuff gets real when you actually make the agreed purchase. Your relationship just went to a new level: the holiday level.
  5. Should I invite him to my work holiday party? You technically have a plus one in your life, but are you at the stage where you feel comfortable enough to take him to your company party? Will he think it’s weird that you ask, or rude if you don’t ask? How will you introduce him to your boss and colleagues? Help!
  6. Should I invite him to family events? Is it too soon? It’s the holidays! You kind of dread attending the events solo when you technically have someone, but much like the thoughts surrounding your company party, you wonder if he’ll think it’s weird or rude if you do or don’t ask.
  7. Is he going to ask me to family events? It would be a lot easier if he asked you first, because then you really know where things stand. If he doesn’t, then you’re stuck wondering if it’s because he’s also dancing around the subject to avoid knowing where the relationship is headed, if anywhere at all.
  8. Are we spending New Year’s together? They say that whoever you kiss at midnight will be the person you spend your year with, so you wonder if he’s thought to make plans with you and if not, who he’ll be locking lips with when the countdown ends.
  9. Will this be fun or just incredibly awkward? The fact is that holidays are always a bit of a stressful time of year, and having a new relationship complicates that a bit. It’s normal for most people, even the dudes, to have these lingering thoughts of what the right protocol is to make it through smoothly. The good news is that if your relationship survives this incredibly awkward time, even if you don’t necessarily attend them all together, you’re off to a great start! Just breathe, relax, and take things in stride.