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7 Awkward pain points for couples exchanging gifts

I started my foray into relationship expertise by making every mistake imaginable. I started blogging about it in 2008.

As relationships get more serious, one might assume that gift giving would get easier. I would argue that it gets more stressful.

awkward couple gift exchange

By the time you're seriously dating, gift giving has lost all its innocence. Gone are the days when you could — at the last minute — make something for Mom and get by on the cuteness, the hard labor and the thought. (Wasn't that what counted once?) As relationships get more serious, you'd assume that gift giving would get easier. I would argue that it gets more stressful.

Here are seven characteristics of couples' gift exchange that make the holidays stressful.

Size matters

When I was in high school, my girlfriend was a size 2. My older sister is in great shape, so when it came time to buy her a gift one year, I assumed she was a size 2 because that was all I knew.

When I gave her the gift, she said, "I haven't been a size 2 since high school."

Unfortunately, clothes are a no-win situation unless you get clear instructions. "This is too small for me" or "You think I'm this big" will not work.

Having to pretend you like it

Even the most novice gift-happiness faker can paste on a smile and dole out the necessary positive vibes in the face of a bad gift. Lest we forget, a truly effective gift-happiness faker uses said gift later on in front of the giver after the holiday lights have faded.

Proving you like a gift can be quite traumatic. Once, as a gift from his dad (who we are all afraid of), my buddy got a ridiculous, shiny sateen Baltimore Ravens jacket — super puffed. (And this was well after the '90s had ended.) Stitched onto the back of this jacket, a giant Ravens head in mid-squawk glared at all who made eye contact.

The ensuing game day, after Christmas, my friend tried to sneak out of his house, but his dad caught him.

"Aren't you going to wear your new jacket?" his dad demanded.

Since then, at subsequent tailgates and game days, my friend has sulked in bar or parking lot corners — puffed and stewing in his beer with the sun reflecting off that jacket as if it were some material in a '60s B-movie space wardrobe.

Figuring out if you're even exchanging gifts

Fledgling relationships fall victim to awkward timing regarding holiday gifts. The discussion has to happen, but someone also needs to initiate that discussion — and sometimes, each person is waiting for the other to initiate it. To those of you who don't think this discussion is necessary, I say buy a gift at your own risk. I have plenty of friends who have gotten a gift only to find out the significant other didn't get one.

Figuring out gifts for each other's family

The next layer of gift giving is the significant other's family. This warrants yet another discussion. Once you settle on giving gifts to each other's family, it adds a whole new roster of people you have to figure out.

Up-front agreements and confirmation

In the past — before the holidays — I discussed with my girlfriends what we should get each other. We made a rule that we had to spend the same amount on each other. So, remind me why we didn't just buy this stuff for ourselves and skip the stress and gift wrapping.

When guys check out on buying gifts

Because of my dad's tightwad ways and/or his general inability to listen, my mom (with some help from my older sister) has been buying her own gifts for as long as I can remember. I always thought it was strange when my mom would guess her gifts marked "To Jo, Love Art" (in her own handwriting).

She'd say, "This must be my new scarf I picked up for myself!"

One of my past girlfriends ordered a jacket she wanted before the holiday, had it shipped to her own apartment, wrapped it and opened it herself. I later wrote her a check. Many of my friends' moms have done the shopping-for-themselves move as well.

Surprises are a no-go

Isn't spontaneity supposed to be the very essence of gift giving? The other day, a female co-worker mentioned that she didn't like surprise gifts from her husband. I must admit that, more often than not, my surprise gifts are failures. Tightroping the guessing line means I'm picking out clothes I think she likes or guessing sizes. But if there's one thing I've learned about operating with a woman within a relationship, it's this: Never assume.

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