Fellow lifty here, I've had two pretty funny moments this year:
1: I was working the bottom of my lift by myself on a slow day when this old guy (likes in his 60's orsomething) comes up to get on, as I am getting ready to bump him he says, and I shit you not "your beard is looking pretty sticky, is it from eating out your girlfriend?" So obviously I'm just standing there like WTF and laughing my ass off. The next time he comes to the lift he says "Not that she's complaining," that was the last I saw of him.
2: Same lift, another slow day. I see a group of gapers coming down the black diamond next to the lift (note, I work in mn at a hill with 300 feet of vertical, so this isn't anything crazy) and the first one does a total yard sale but is fine. Next a snowboarder chick makes it down fine and then there was this last guy who is just straightlining it to the trees. I though for sure he was gunna smack hard but then catches his ski on something and just tomahawks right at the base of the hill. Ended up cutting his neck and (I think) needing stitches.