A relationship with a big age difference can be a challenge, but it doesn't necessarily mean it's doomed. Rabbi Shmuley discusses the ups and downs of May-December romances—relationships in which one person is significantly older than the other.
Rabbi Shmuley says as long as the age difference is not too large, a May-December romance is acceptable. For example, he says, an age gap of a five to 10 years is a suitable difference. A generation gap of 25 years or more, however, should be avoided, he says. "There's really no good reason to date someone that's 25 years different than you."
Today's Shmuleyism
"In May-December romances, age gaps are okay, but generation gaps are a really bad idea. Avoid the pitfall of ever equating youth as the soul ingredient of beauty."
