Leonardo Dicaprio won't date anyone older than 25. There's a video by coach Red Pill called "Never date a girl over 25." A lot of red pill youtubers say the same thing that any women over 25 is damaged goods and isn't worth being with. Leonardo Dicaprio won't date anyone older than 25.Are you supposed to dump your gf when she turns 26 and get the next 20-25 year old lol?