Stars who date younger men Model Chantel Jeffries has been in the spotlight since she was photographed with Justin Bieber before his arrest in Miami on January 23. It's unclear if the two are dating or are just friends, but if she gets into a relationship with him, Jeffries will be the latest older lady who's fallen for the pop star: She's 21; he's 19. Jeffries also wouldn't be the only celebrity who dates younger -- take a look: