Before we were married my husband gave me two DIY Readers Digest books of home repair for Valentine's Day when I was kind of expecting a proposal. I might have burst into tears. He tried to explain that, as he had just put a contract on a house, that it was his way of asking me to live with him.
He did better at my next birthday. I got a kitten and a hose, and bucket- having a pet and being able to wash my car were why I wanted a house.
His mother sucked at gifts, too. She'd buy random things at craft fairs because she felt badly for her single teacher-mom colleagues trying to make ends meet. A lot of oversized sweat shirts with appliqued cats, puffy paint and bedazzle. (I'm pretty crafty, so if I'd wanted such things, I'd whip them up at home). She alternated years with DH- one year a Cross pen and the next a blue oxford cloth shirt that was too small in the collar and too short in the sleeves.
When DS's babysitter was being treated for anorexia, her grandmother gave her an open bottle of GNC Multivitamins.
One year DH got me a fancy wine opener and stoppers. I was pregnant at the time and not pleased, although I've gotten a ton of use out of it since then.
For my 40th birthday, MIL sent a $25 GC to Kohl's. It was blank.