Ben Affleck

Ben’s dating history includes strippers, gambling and multiple exes. After leaving Jennifer Lopez for Jennifer Garner, Garner and Affleck enjoyed ten years of marriage and three lovely kids. However, rumor has it that Affleck was caught cheating on her, and the couple divorced shortly thereafter.

John Mayer

Mayer’s melodious voice and seductive skills have earned him a reputation in Hollywood. He’s dated everybody from Taylor Swift to Jennifer Aniston to Minka Kelly. Serial dating told Ellen Degeneres in 2009 that relationships scared her. Can you say red flags?

Ryan Gosling

Who does not love Ryan Gosling? After Notebook aired, Gosling and co-star Rachel McAdams developed a real relationship before it fizzled out and Gosling became the face of each meme on the internet. It seems he has finally settled down with Eva Mendes, with whom he now shares a child.

Bradley Cooper

Cooper, was named the Sexiest Man Alive by People, seems to have a thing for blondes. He has been romantically linked to Cameron Diaz, Jennifer Aniston, and most recently, Irina Shayk. The pair split after four years together following its release A star has been born. Fans have wondered if the chemistry between Cooper and Lady Gaga had anything to do with the split.

George Clooney

Clooney for sure That Hollywood’s famous bachelor. Women and men alike want to date him. He has a long list of exes he left behind, including ex-wife Talia Balsam. Has the guy finally decided to settle down? He has now been married to Amal Clooney since 2014 whom he seems to actually like. The couple share a son and daughter together.

Leonardo DiCaprio

Known for dating super models and younger women (largely under the age of 25), DiCaprio’s dating record is second to none. Leo is getting older, but his girlfriend is still the same age. Looks like Leo has been dating science.

Orlando Bloom

This one may come as a little bit of a surprise to some. From Lindsey Lohan to Miranda Kerr, Bloom shows us that not everybody has a “type.” He is now engaged to Katy Perry; however the couple stated that they slowed down the marriage planning because they weren’t in a rush to get married.