How have we done 70 of these alleged dating histories and not taken a look at Bruce Willis’ list of girlfriends, wives, and flings? Let’s remedy that today. Willis, 58, has been with the same woman since 2008, but that still leaves a lot of years for one of the most popular actors in the world to have hooked up with some sexy, famous women. The question then is, how many? Read on to find out.
Photo credit: Bruce Willis image by Featureflash/Shutterstock
Janice Dickinson (Dates unclear)
Not sure of the dates here, but Dickinson was once quoted as saying, Willis “was the kind of sweetheart who bounded out of bed to go buy you breakfast.”
Hookup score: 9.0
She was the “original” supermodel back in the day, after all (at least according to her).
Photo credit: Janice Dickinson image by Helga Esteb/Shutterstock
Linda Fiorentino (1978-1982)
All we have on this relationship is that it supposedly lasted for four years.
Hookup score: 9.0
You guys remember Linda Fiorentino, right?
Photo credit: Linda Fiorentino image by Featureflash/Shutterstock
Demi Moore (1987-2000)
Moore and Willis met at the screening of the movie Stakeout and shortly thereafter Demi broke off her engagement to Emilio Estevez. Demi and Bruce were then married the same year.
Hookup score: 9.5
This relationship was so much more fun than Ashton-Demi.
Photo credit: Demi Moore/Bruce Willis image by Featureflash/Shutterstock
Lara Flynn Boyle (2000)
Boyle allegedly left Jack Nicholson so she could start dating Willis.
Hookup score: 9.0
This was right at the tail end of Boyle still being a little hottie.
Photo credit: Lara Flynn Boyle image by Featureflash/Shutterstock
Rachel Hunter (2001-2002)
Scant details are available on this relationship other than it reportedly took place.
Hookup score: 10.0
An SI Swimsuit Issue legend.
Photo credit: Rachel Hunter image by Featureflash/Shutterstock
Emily Sandberg (2002)
Again, very little information other than Sandberg was one of several women Willis was spotted with after his divorce from Demi.
Hookup score: 8.5
She’s a model, not a super famous one, but a model nonetheless.
Photo credit: Emily Sandberg image by Featureflash/Shutterstock
Rachel Sterling (2002)
Actress Rachel Sterling is just another one of the ladies that Willis allegedly spent some time with after his divorce.
Hookup score: 8.5
Boring.
Photo credit: Rachel Sterling image by s_bukley/Shutterstock
Kim Cattrall (2003)
Willis and Cattrall allegedly dated for a little while after meeting at a party.
Hookup score: 9.5
2003 Kim Cattrall was the hotness.
Photo credit: Kim Cattrall image by Featureflash/Shutterstock
Brooke Burns (2003-2004)
Baywatch babe Brooke Burns and Bruce Willis were actually engaged, but broke up after only 10 months citing her being Hawaii shooting her show kept them apart too much.
Hookup score: 9.5
Too bad. This would have been a fun couple.
Photo credit: Brooke Burns/Bruce Willis image by Featureflash/Shutterstock
Lindsay Lohan (2005)
Keep in mind Lindsay Lohan is 27. NOW. And five years older than Lindsay’s father. But it was still reported that “they couldn’t keep their hands off one another” at a party.
Hookup score: 9.0
No surprise. Lindsay is pretty much all on of these lists.
Photo credit: Lindsay Lohan image by carrie-nelson/Shutterstock
Aida Yespica (2005)
Venezuelan model Aida Yespica is 31. NOW. Bruce Almighty.
Hookup score: 9.5
This is why we love Bruce Willis, people.
Photo credit: Aida Yespica image by emipress/Shutterstock
Karen McDougal (2007)
Willis and McDougal (Playmate of the Year 1998) definitely dated as there were numerous photos of them together being more than just friends.
Hookup score: 10.0
Playmate of the Year, people.
Photo credit: Karen McDougal image by s_bukley/Shutterstock
Emma Heming (2008-present)
English model Emma Heming and Bruce Willis were married in 2009 and had a daughter together in 2012.
Hookup score: 9.0
Demi and Ashton were at the wedding ceremony. How nice.
Other less-substantiated alleged flings: Lisa Barbuscia, Nadia Bjorlin, Louise Griffiths, Cybill Shepherd, Estella Warren, Tamara Witmer, Renee Zellweger
Photo credit: Emma Heming/Bruce Willis image by s_bukley/Shutterstock
Final Tally
Bruce Willis’ Hookup Score: 120 points
And we have a new entrant into the top five. Not like we expected anything less from Bruce Willis, did we?
1. Leonardo DiCaprio – 187 points
2. Jack Nicholson – 163
3. Charlie Sheen – 136
4. Bruce Willis – 120
5. Tommy Lee – 111
6. Sean ‘Diddy’ Combs – 110
7. Stephen Dorff – 109.5
8. Jamie Foxx – 108.5
9. Jared Leto – 108
10. Vin Diesel – 100.5
11. Cristiano Ronaldo – 99.5
12. Russell Brand – 99
13. Seth MacFarlane – 98
14. Tiger Woods – 93.5
15. George Clooney – 93
16. Tom Cruise – 92.5
17t. Benicio Del Toro – 91
17t. Josh Hartnett – 91
19. Chris Evans – 83.5
20t. Justin Timberlake – 82
20t. Ryan Phillippe – 82
20t. Tyson Beckford – 82
23t. Ben Affleck – 81
23t. Orlando Bloom – 81
25t. Tyrese Gibson – 80
25t. Derek Jeter – 80
27t. David Duchovny – 78.5
27t. Marilyn Manson – 78.5
29. Owen Wilson – 77.5
30. Joe Jonas – 77
31. Ryan Reynolds – 75
32. Ashton Kutcher – 73
33t. Harry Styles – 72.5
33t. Jeremy Piven – 72.5
35. Ryan Gosling – 72
36t. Kanye West – 71
36t. Brad Pitt – 71
36t. Jude Law – 71
39t. Colin Farrell – 70
39t. Adam Levine – 70
41. Sean Penn – 69
42t. Taylor Lautner – 67
42t. Johnny Depp – 67
44t. Ian Somerhalder – 66.0
44t. Jake Gyllenhaal – 66
46. Andy Roddick – 64.5
47t. Tom Brady – 64
47t. Mark Sanchez – 64
47t. Joseph Gordon-Levitt – 63
50t. Zac Efron – 63
50t. Adrien Brody – 63
50t. Adam Brody – 63
50t. Kevin Connolly – 63
54. Chris Pine – 62.5
55t. Michael Phelps – 62
55t. Adam Duritz – 62
55t. Alexander Skarsgard – 62
55t. Wilmer Valderrama – 62
55t. Gerard Butler – 62
60. Liam Neeson – 61.5
61. Criss Angel – 61
62. John Mayer – 60
63. Bradley Cooper – 57
64. Shia LaBeouf – 56.5
65t. James Franco – 53
65t. Alex Rodriguez – 53
67. Will Smith – 52
68. Robert Downey, Jr. – 51.5
69. Edward Norton – 51
70. Paul Walker – 48.5
71. Matthew Morrison – 47