When one of my daughters was about junior high age, a relative gave her a hairpiece that the relative used to wear back in the 60’s I think. I’m not even sure exactly what the proper term for it is or how you would wear it. She thought it matched D’s hair and she could wear it too. In our house it’s called “the toupee.” The kids get some pretty odd gifts from grandmas now and again, but “the toupee” reigns as the strangest!
One year a relative made all of us t-shirts with different scenes from our then-favorite tv show with each person’s face photoshopped into his/her own shirt. It was funny, but actually wearing them wasn’t happening.
To continue the lingerie theme, as teenagers a friend and I were out shopping together and each bought our moms the tackiest pair of underwear we could find for Christmas. Think dollar store, lime green and black. They were regifted several times over the years on special occasions!
Several years ago we had a couple over for swimming and a BBQ and they left their wet swimsuits hanging in the bathroom. A couple of months later it was Christmastime and we had planned a get together with them again, so I took the swimsuits, which I had washed, and wrapped them up in a beautiful box with lavish paper and bow. When we saw them we presented them with their “Christmas Gift” and I could see the wife giving her husband the side-eye, embarrassed that they had brought nothing for us. They were so gracious, carefully opening the wonderful gift, then, when they saw their old, forgotten swimsuits, they burst out laughing. It only worked because they had a sense of humor.
Not Christmas but I have a good birthday story. One year we had some family members over to celebrate DH’s birthday. The seven of them arrived all bearing separate gifts of assorted sizes and wrappings. DH opens the first one and it is a single pair of socks.
DH says, “Thank you, I really need new socks.”
Cousin says, “Yes, I noticed you had holes in your socks last week at our place.” Everyone laughs, me louder than anyone. DH opens next gift, another single pair of identical socks. Again everyone laughs, me louder than anyone.
Next gift, same thing and so it goes until he has opened all of their gifts. DH grabs my gift and says, “At least I know it won’t be socks.” Except of course it was. Not only that it was the exact same socks (package of 6 with one pair free). I had been mortified at the hole a week ago and thought it would be fun to gently embarrass him. His real gift was a ceiling fan that I knew he would want to help out. I just didn’t expect the whole family to have the same thought.
I was mortified after opening Christmas gifts for the first time as an official family member when my MIL gleefully shared that she had rummaged through my suitcase on an earlier visit so she could buy the right size. I would have preferred the wrong size than someone pawing through my personal items.
For Yankee Swap one year I got a hedgehog boot scrapper thing. It was bristled. When I opened the box, I shrieked when I saw the beady eyes because I thought it was roadkill. That Christmas punch.
My DH has an old, eccentric, poor bachelor uncle that we help support financially. He always sends gifts to me and our children for Christmas - but he is not quite right in the mind so it is always a mystery. Some years he gets us all, some years just some of the kids, some years just me. NEVER my DH, his nephew. My MIL is really good and when she brings his gifts to us she would make sure there were things for everyone and fill in if one of the kids was left out. Interestingly he would only acknowledge 2 of my SIL’s 4 kids - and never the same 2. He shops at the salvation army and the church resale shop, although once and a while we get really expensive (yet inappropriate gifts) He gave my 3rd grader a cell phone once and my 14 year old a knock off Barbie from the Dollar General - in the same year!
The best was my now college freshman DD was at the tough preteen age of 10-11 and opened a used romance novel from the 80’s in front of our entire family and all of her cousins. It had a nearly naked women on her knees in front of a shirtless man on the front cover and was entitled something like “Hot Unbriddled Lovers”. It was clearly from the used book store and had dog-eared pages. My MIL not realizing what kind of book it was said loudly - “oh finally a good gift - he knows you love to read… what is it about?” My daughter was a bit naive and clueless about the genre (although embarrassed about the cover) and turned the book over and read the back (thankfully not out loud!!) and I thought she was going to die. We quickly wisked the book away but have since had lots of laughs over it. It has made an appearace at different gift giving times around the family and now that DD is 18 I think we need to cycle it back her way just for some memories!
When DH and I were still young newlyweds, my in-laws relocated to our city. Our first Christmas together, crazy DH proudly got me a red sheer baby doll nighty set. (Fredericks-style.) I was so embarrassed. But worse when I opened my gift from MIL - a long red plaid heavy flannel prairie nightgown. She said maybe it would help me avoid the flu.