The DiCaprio thing is funny.
In the 80s or 90s everyone knew that a movie star having a series of young starlet girlfriends meant they’re gay. They get a beard to cover their sexuality and the girlfriend gets exposure from having a famous boyfriend. They split up because it’s obviously not a real relationship, and the studio finds some new actress to link him to.
But being gay got so much more acceptable recently that people don’t understand being closeted any more. So they think DiCaprio is a dirty old man who will only date 22 year olds.
Only if something unusual has happened. Otherwise it’s just small talk about work and your family’s health. By a certain age there’s basically never anything “new” in your life.