People don’t seem to enjoy being told, “You look tired.”

This is especially true in cases in which this is said to a girl.   I don’t really think of it as an insult though.  Sure girls seem to equate looking tired to not looking good, but I don’t see it that way.  You can still be hot/cute/pretty, but just a more tired version…

If I say to a girl that she looks tired, she should almost be appreciative!  It’s as if I care about her so much, am so observant, and pay such close attention to detail, that this should all come across as genuine concern.

All I’m saying is 10 out of 10 times a cute girl who’s tired will still be more attractive than an ugly girl who’s had a good night’s sleep.