18. Justin Timberlake and Jenna Dewan-Tatum
Pop superstar JT is now long married to Jessica Biel, and Jenna Dewan-Tatum is very famously partnered with Channing, of course. But back when she was plain old Dewan, Jenna was a backing dancer for Timberlake. And after his devastating break-up with Britney, Jenna helped him get back in the saddle, so to speak.
17. Amanda Seyfried and Ryan Phillippe
Mamma Mia!’s Amanda Seyfried and Ryan Phillippe of Cruel Intentions fame first laid eyes on each other at Kate Hudson’s Halloween party. They’d both done a bit of imbibing and ended up going home together. They dated off and on for seven months, but Seyfried says they were a mismatch from pretty much day one!
16. Sandra Bullock and Ryan Gosling
Yes, the La La Land star was once involved with none other than Sandy Bullock – who is a full 16 years his senior. It was way back in 2002, but they both still speak fondly of each other. Gosling clearly has a thing for the older ladies, as his wife Eva Mendes is also older by seven years.