After DIL gave birth to twins she was out alone after about 2 months and someone asked her when her baby was due.
Going by her histrionics about it I assumed she did not feel complimented, at all.
(She did lose the extra weight)
Your glasses make you look smart. Uhh… OK. Thanks?
(back when I used to wear glasses)
I absolutely cringe when I remember this but in my callow youth I asked someone what they actually did with a liberal arts degree. I’ve never seen that person again but I wish I could so I could apologize. I think compliments are amazing if they are heartfelt.
Mama Plant told me, “You don’t stink so much since you quit smoking”.
Somebody told me that once, and my reply was “What little hair you have left has dandruff in it.” The look on his face was priceless!
I have a kind of eclectic style of dress that sometimes elicits compliments. One co-worker looked at my outfit and said “only WOOK could pull that off”.
Would that be in the same way that only Sideshow Bob could pull of that hair? 
I first encountered it in the Viz comic - a character named Sid the Sexist, who exclaimed "Tha divent sweat much for a fat lass!’
I have a whole collection of these I’ve heard (and been subjected to) over the years. My absolute all-time favorite was my mother-in-law upon meeting her son’s soon-to-be third wife. “Oh, you’re lovely! Much prettier than the other two.”
I was about to begin a minor home improvement project, and my wife hit me with her own version of an affirmation. “I’m sure it will be the very best you can do.”
You smell better than usual.
I often tell my little brother (who’s nuts, btw) “For the black sheep of the family you sure are a good brother!”
He takes it well.
As in, he’s never punched me.
Hahaaha. Yeah, i had a Father in Law that was very sweet and honest (he’s since passed away). Got him in trouble a lot.
My (now) wife and I flew to her hometown so I could meet her parents. Conversationaly I ask my FIL to be if he had any trouble getting to the airport - FIL: “No, and I haven’t been here since (wifes name) brought that other guy home” 
“What, what did I say?”
I knew I was gonna like this guy.
That doesn’t seem so bad to me. I know what I do with my mechanical engineering degree, and my background there gives me some sense of what other types of engineers do with their engineering degree. But “liberal arts” is such a general and abstract description and so far from my own area of expertise that without more info, I just have no idea what kind of work someone with an LA degree does. Is it rude to be curious?
I’d be proud if someone said that to me. I read an article today pointing out that Rob Lowe is now 60, and I had exactly that thought: when I hit 60, I hope I look as good as he does (I won’t).
Back in the 80s there was a little dive bar in Detroit that some college buddies had started hanging out at. It was also a hangout for Vietnam vets. I got in the habit of going for a couple beers and a few games of pool every Thursday night.
The vets, a generation older than us and pretty wild, were all characters. I had a pretty decent pool game, but they were all insanely good. I could often beat my college buddies, but very rarely the vets.
One time I was playing a game with a vet, an enormous, maybe 6 foot 5 biker-looking guy with a long beard who was very intimidating. I had my best game face on and almost, but not quite, beat the guy, finishing with a long green across the table shot and a very difficult bank-combo that I both made before I missed and he took over and put the 8-ball away.
After he won he came up to me and said “you know what, when we started the game I thought ‘who is this scrawny little dorky-looking pipsqueak to challenge me to a game?’ But I have to hand it to you-- you really stepped up and made a couple amazing shots. There’s more to you than I thought. I gotta say…”
“…you’re a real Sonny Bono!”
As @Machine_Elf says, not in itself a particularly rude or embarrassing question.
As a graduate of a school with a unique classical liberal arts program, we use to joke that our degree qualified us to be bartenders.
Interesting. I’ve often commented that people were intelligent and enlightened despite having a higher education. I was usually lying though.
your hair looks nice today - did you wash it?
or one that I actually use (among good friends) … congrats on getting rid of your fungal problem
See, this is why I’m hesitant to hand out compliments.
“Others may say you are not fit to live with pigs, but I think you are!”
Two probably pointless anecdotes:
Someone on this board once told me, in our (so far) only meeting in person, and in front of others, that I wasn’t anything like he thought I would be (presumably this was based on my posting here). No elaboration or further comment.
My husband, waaaay back the first time we had a close personal encounter, said “You don’t smell!” Considering he is Japanese, the way he said it, and the fact that I knew it to be true*, I took it as a compliment. In my patented ironic style, I said “Thanks, neither do you.” It was ironic because he was wearing a nice cologne.
*I had, after all, recently showered, as one does in such situations.