The Mature Single’s Guide to Stress Free Holiday Gift Giving

Giving gifts on a date - mature daters

It’s The Holidays. That oh so awkward time for those who are dating or in a new relationship. Yah, you’re dating after 40, but you may still have the same questions about gift giving that you had when you were 20: Do I give him a gift? If, so what? What if I get him something and he doesn’t get me anything? Or vice versa?

If you’re in an exclusive relationship, and have been for some time, I’m assuming you know each other well enough to figure out the gift giving thing without me. But for those of you who have been with your man anywhere from several weeks to just a few months, I’m going to make it easy for you by giving you a couple stress-free gift-giving guidelines (GGGs).

#1: Communicate With Your Man Like a Grownup

Have a conversation in advance of the holidays about each others’ expectations. You might start by sharing what you like to do, what plans you’ve already made, who you like to share your time with and what gift giving means to you.

This isn’t about telling him what you want so he rubber stamps it. Share what makes you happy, and then tell him clearly that you want to hear how he likes to enjoy his holiday season. You are starting a conversation so you can collaborate and come to some decisions that will please you both during the holiday season.

This is the great thing about “mature” dating and relationships. You can have honest, meaningful discussions about things that matter. Games and guessing be gone!

#2: Keep Your Expectations and Perspective in Check

Keep in mind that your man may be even more stressed out by the gift-giving conundrum than you are. Men feel a lot of pressure around this time of year. This is one reason men (and some women) end emerging relationships before the holidays; to avoid the drama around gift giving.

Your man may want to make you terrifically happy, but unless you followed my advice above, he may have absolutely no clue how to do that. If you don’t receive what you hope for or he gives you something you don’t like, give him the gift of appreciation and understanding. He is with you, and he made the effort to please you. That deserves some major points in my book.

You can have honest, meaningful discussions about things that matter. Games and guessing be gone!

Remember, too, that this is just one day in the journey of your budding relationship. Maybe he still feels he’s getting to know you and doesn’t quite know what you like so he gave it his best shot. Or maybe he isn’t quite “there” yet, so he doesn’t want to give you the wrong message. That doesn’t mean he can’t turn out to be the love of your life!

Don’t over-analyze what you receive or put too much emphasis on his gift. (Or even the lack of a gift.) This is just a tiny, tiny part of your overall relationship.

#3: Don’t Over-Give

When it comes to gifts, chose a gift that says “I’m thinking of you” or “I’m happy to have the opportunity to do something nice for you.” Don’t make your gift something that says “I’m assuming we will be together forever” or “I’m trying to impress you.”

In the beginning of a relationship I would err on the side of too little rather than too much. Choose something that isn’t too expensive, but make it personal and tells him you listen and care about him.

Here are some safe gift ideas:

  • A copy of your favorite book with an inscription as to why you like it and are sharing it with him.
  • A bottle of his favorite spirits, wine or champagne.
  • An invitation to an exceptional meal; home cooked or at a special restaurant.
  • A bag of exotic coffee beans or loose tea, with a couple of mugs.
  • A concert t-shirt or memorabilia from his favorite band.
  • A box of fine chocolates. (Yes, many men like these too.)
  • Golf balls or personalized tees, if he is a golfer.
  • A fine manicure travel kit. (I bought this for my husband and he loves it.)
  • Some hand-selected gourmet food items, in a nice basket.
  • A gift certificate for a massage.

You can add a personalized card or note to any of these to make them more special, flirty or romantic, depending on where you are in your relationship. With the bottle of wine you can add a note that says “This would be delicious with my famous Pasta Bolognese. Are you game?” Or, include a note with your invitation to dinner that lets him know how much you appreciate all he does for you and that you’re looking forward to “showing him a great time.”

#4: In the End, Take Care of Yourself

When in doubt, get him a gift, wrap it up and make sure you keep the receipt. Better yet, make it something you like as well. This way, at the last minute if you feel it’s too awkward or you are just not “feelin’ it” you can return it or enjoy it yourself. After all, you deserve a nice bottle of champagne or box of chocolates, right?

Now it’s your turn. What are your gift giving ideas and tips to help relieve the drama of it all? We want to hear from you!


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