“OOmis – I haven’t addressed you in a long time, but since when is it now taboo for an older guy to try and get a date with a younger woman? In my opinion, it’s polite to say to the guy -“No thank you”. This is the preferred torah way. Instead of detesting other Jews, it’s more polite to say no and not be Oiver “Lo sisna”. They wouldn’t be so disgusted if they immediately let the other party know the score. They wouldn’t bottle up their bad feelings. It would bother them a second with a “Eew”, and then they would forget about it. Your definition of being polite, only causes the male to keep trying, and then this causes the female to build up more resentment. “
Health, it is not taboo (yet would not the reverse be taboo, that of an older FEMALE of that age, dating a very much younger guy?), but it nevertheless is awkward. The guy comes of as a predator, if the girl is really much younger. It is simply inappropriate for a 40 year old to go after a 25 year old. and when it happened to my friend’s daughter, she could not get rid of the guy, who to his credit, was a pleasant enough fellow, but did not accept that he was making her very uncomfortable. She didn’t want to hurt his feelings or be rude, but he really followed her around. This made her feel very eckled.
It is not so easy for a girl to say outright to someone to please stop following her because he is not the right age for her. It’s also why I personally think that singles events should stick strictly to an age limit within five years of the oldest female present. Once the female are in the mid-late thirties or more, there is no shaychus to them being in a singles event with girls in their mid twenties to 30 or 31. And if divorced/widowed fellows are present (and should be), the age should be appropriate.
You may disagree, Health, and I get that you do, but a normal mid 20’s girl will likely feel that a guy 15 years older who is pursuing her, is a bit creepy. The guys also cannot seem to accept that they are not so desirable to that much younger demographic. they need to accept and act their age, which is still young, by all means, but not as young as they seem to think they are. Nothing is taboo (except what Hashem says is taboo), but such guys look extremely socially awkward, and they would do far better to go for more realistic shidduchim with older women than the ones they are scouting out.