Kris Jenner & Cory Gamble
Come on, you had to guess that a Kardashian or two would end up on the list. Well, she’s still a Jenner technically speaking. So, mamma Kris Jenner has 25 years on her boyfriend, Corey Gamble. While she says marriage is not something she’s thinking of, these lovebirds have been happily dating since 2014.
Kris Jenner & Corey Gamble
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Suki Waterhouse & Bradley Cooper
Wow, we truly miss this adorable Hollywood romance! Did you even realize that Bradley Cooper was a whole 17 years older than Suki Waterhouse? Anyway, they began dating in 2013 when she was 21 years old and Bradley Cooper was 38. Sadly, they ended things in 2015.
Suki Waterhouse & Bradley Cooper
