Not funny, but definitely cringeworthy:
Our tour guide at a college about an hour west of Boston was heavyset. As we went into the dining hall, she said enthusiastically “This is the best part of campus, because who doesn’t love food!” So awkward.
I was told this third-hand and can’t vouch for its truth, but this allegedly occurred at a well-known Midwest LAC. The tour group was touring and a girl on campus pulled up her T-shirt to expose her pierced, um, lady lumps. This is not the LAC that begins with O.
We visited Penn State on an unseasonably warm February day. Everyone was out in shorts and T-shirts. I believe this is common, but shortly after the tour commenced, a student on campus walked by our guide and shouted “We are!” Without missing a beat, the guide shouted “Penn State!” It happened again, but this time everyone is the group shouted back “Penn State!” Then it happened a third time. It was fun and definitely impressed my kid.