Is this a horrible thing to say or just careless?

Hey guys. So a female friend of mine, Naomi* was set up by another friend of ours, Steve* to go out with this guy, Darren*. They got along really well and have been seeing each other for a few months now. The thing is, the other night they were just talking about anything and everything and Darren very casually said to Naomi that before their first date, Steve raved on about how she was so pretty and even likened her to a supermodel. Darren then went on to say that although she was pretty, she certainly wasn't THAT pretty and Steve was such a drama queen to even think such a thing. Naomi just took it and laughed along but afterward felt really bad about herself. She doesn't know whether he was at fault or whether she should stop being so vain. Now, I've already told her what I think but she would like to know what all of you think.