Who has dated the most celebrities?

14 Hollywood Celebrities Who Have Dated a LOT of PeopleKim Kardashian – 11. John Mayer – 12. Kirsten Dunst – 15. Jennifer Love Hewitt – 17. Madonna – 22. Justin Timberlake – 22. Paris Hilton – 23. Leonardo DiCaprio – 28.More items •11 Jan 2017

Do celebrities ever date non celebrities?

“Celebrities can successfully date ordinary people as long as theyre both aware they will be publicly scrutinized and that their lives may be dictated by the celebritys appearance and production schedule.