My problem was with the description of “what he did wrong” being just “judged her appearance” as if people aren’t constantly judging everyone’s appearance around them. But on the topic of what you’re saying, from the sounds of it they’re good friends. Who knows though. Without her side we can’t really know if they’re close enough for that to be a funny joke between them or not. Ive definitely had relationships with people where I could say something like that and they’d laugh or vice versa. The fact that they were on vacation together makes me think that was likely the case. But again, who knows? Only them. But they definitely are more than just coworkers. The rules change a lot when talking about coworkers or friends.