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Holiday Shopping for Your Date

It’s very common for “Holiday Hookups” to happen this time of year. There are company holiday parties, friends parties, and of course New Years Eve.

However, as soon as you start dating someone, you do face the gift giving dilemma.

  • Do you get them a gift?
  • How much do you spend?
  • What if they don’t give you a gift back?
  • Will they feel pressured?

It’s enough to make your head hurt.

So much depends on several factors, too many variables for me to cover in one blog article. However, here are some things to ask yourself and some rules of thumb you can use to help ensure you don’t become a Grinch.


  1. How long have you been dating?
  2. Have you discussed Holiday plans?
  3. Have you discussed gift ideas?
  4. Has the other person been avoiding any holiday talk?
  5. Do they celebrate the same holidays that you do?

Ask your self these questions and seriously think about your answers. The longer you have been dating, the more significant (at least in meaning, not in dollars) the gift should be. If you have plans to actually spend Christmas Eve, or Christmas Together, a gift would be appropriate. If you have actually talked about what you want as gifts, you are giving the all clear for some shopping.

However, if he’s been avoiding holiday talk like the plague, and getting very non-committal about holiday plans, signs are good that he’s just not ready to take the relationship to the wrapping paper level. For the guys you’ve just started dating, or are dating on a very casual level (but not just booty calls), there are a few things to take into consideration.

Rules of Thumb:

  1. Don’t go overboard. I once spent days tracking down a signed copy of a boyfriends favorite book by his favorite author. It was a bit overwhelming for him, even though we had been dating at that point for several months. There is often a feeling that gifts need to be equal, and setting the bar to high can either scare the guy off or make him feel inadequate in the package department.
  2. Do put thought into the gift. Unless you know it’s what he really wants, a gift card is just a little impersonal for someone you are interested in. If you get him something that reflects and interests, you will show that you have really paid attention to things he’s said.
  3. Don’t go for “couples” gifts. It’s probably way too soon to get the matching t-shirts with your photos on it. Any gift that screams “I’m already planning our wedding” is going to make the other person uncomfortable.
  4. Do get something fun. A practical gift in my house is referred to as an “Aunt Edna” gift, because she always gave something practical, useful and BORING. You are not at the point where socks and underwear are a good gift. Unless the relationship is an exclusive, sexual relationship, even sexy underwear is a big no-no.
  5. Don’t give to get something back. If you are going to give a gift, give it for the sheer joy that the act of giving brings. Go into it fully prepared that you might not get a present at all, or that it might not equal what you have done. Have no expectations, and then if you do get something back, it will be wonderful, and you won’t face disappointment.

As we are inundated with commercialized gift giving, it’s hard not to set up expectations of the “perfect” holiday. However, mentally check yourself, and just enjoy spending time with someone you like, and who likes you back.

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