Dear Prudence,
I (a married woman) just set up a single male co-worker and a single female friend of mine on a blind date. He’s a sharp guy who’s traveled the world and knows all about fine foods, wines, classical music, designer labels, etc., and she’s a stunningly beautiful and intelligent artist. I really thought they’d make a great couple. Immediately after their date, my friend thought it had gone well and was very excited. On Monday morning, I asked my co-worker, and he said my friend was attractive and a nice person, but he wouldn’t be asking for a second date.
My friend has been bewildered by her difficulty in finding a steady relationship, so I pressed him as to why. He told me they went to a swanky bar, and she—wait for it—ordered a plain glass of milk. He found this so clueless and childish that he couldn’t imagine being with her. Now my friend is neither a big drinker nor a teetotaler—just someone who’s going to order what she wants without worrying about what others think. Should I tell her why she won’t be hearing from this guy again, so she can reconsider ordering milk on dates in the future? Should I tell him how ridiculous he is for judging someone for something so petty?