Ranking the hot hookups of Owen Wilson

Owen Wilson dating history girlfriends

Owen Wilson image by s_bukley/Shutterstock


With Owen Wilson recently reuniting with Vince Vaughn for the film The Internship I thought this would be a good week to take a look at Owen Wilson’s alleged dating history. His buddy Vince has been married for some time now, but that’s not been a real problem for Owen as he’s hooked up with several famous women over the years. How many famous women? Read on to find out.

Photo credit: Owen Wilson image by s_bukley/Shutterstock

Angel Boris (Date unclear)

Angel Boris

Angel Boris image by s_bukley/Shutterstock


Angel Boris once told Howard Stern that she and Owen Wilson never dated, but did have sex. Nice.

Hookup score: 8.0
Just like you, I too had no idea she was an actress, but she is!

Photo credit: Angel Boris image by s_bukley/Shutterstock

Amber Hay (Date unclear)

Amber Hay

Amber Hay image by s_bukley/Shutterstock


I don’t know who Amber Hay is, but she and Wilson allegedly dated. She’s pretty.

Hookup score: 8.0
Another actress I had to look up.

Photo credit: Amber Hay image by s_bukley/Shutterstock

Mei Melancon (Date unclear)

Mei Melancon

Mei Melancon image by s_bukley/Shutterstock


Once again, I have no idea who she is, but trust me, she is an actress!

Hookup score: 8.0
Hang on, the list gets better.

Photo credit: Mei Melancon image by s_bukley/Shutterstock

Sheryl Crow (1999-2001)

Sheryl Crow

Sheryl Crow image by s_bukley/Shutterstock


Finally, someone we know. Wilson and Crow began dating after they met on the set of The Minus Man. The Minus Man?

Hookup score: 8.5
They reportedly are still good friends so that’s nice.

Photo credit: Sheryl Crow image by s_bukley/Shutterstock

Gina Gershon (2000-2002)

Gina Gershon

Gina Gershon image by Featureflash/Shutterstock


Not much to report here as the Internet is pretty bereft of details, but I am pretty sure they were once a couple.

Hookup score: 9.0
Pretty sure.

Photo credit: Gina Gershon image by Featureflash/Shutterstock

Demi Moore (2002)

Demi Moore

Demi Moore image by s_bukley/Shutterstock


Again, no real details, but as before I am pretty positive that they were an item at one time.

Hookup score: 9.0
His list is getting better.

Photo credit: Demi Moore image by s_bukley/Shutterstock

Kate Hudson (2006-2009)

Kate Hudson

Kate Hudson image by CarlaVanWagoner/Shutterstock


And heeere’s the one everyone knows all about, since it was a thing not once, but twice as they broke up in 2007 only to get back together, only to break up again.

Hookup score: 9.0
The force was strong in Kate…to Owen…or something.

Photo credit: Kate Hudson image by CarlaVanWagoner/Shutterstock

Jessica Simpson (2007)

Jessica Simpson

Jessica Simpson image by s_bukley/Shutterstock


Reportedly Owen and Jessica were spotted on a date in Los Angeles where “he couldn’t keep his hands off her.”

Hookup score: 9.0
I like his style.

Photo credit: Jessica Simpson image by s_bukley/Shutterstock

Le Call (2007)

Le Call

Le Call, Twitter


Apparently she’s a famous model…named Le Call. Did not know that. Anyway, they were seen out together several times in New York, but never confirmed anything.

Hookup score: 9.0
Le Call? And she’s American. Oh, it’s short for LeAnn. That makes a lot more sense.

Other less-substantiated alleged flings: Jennifer Aniston, Xhoana Xheneti

Photo credit: Le Call, Twitter

Final Tally

Owen Wilson’s Hookup Score: 77.5 points

Not too shabby considering that he spent the better part of four years shackled to Kate Hudson.

1. Leonardo DiCaprio – 187 points
2. Jack Nicholson – 163
3. Charlie Sheen – 136
4. Tommy Lee – 111
5. Sean ‘Diddy’ Combs – 110
6. Stephen Dorff – 109.5
7. Jamie Foxx – 108.5
8. Jared Leto – 108
9. Vin Diesel – 100.5
10. Seth MacFarlane – 98
11. Tiger Woods – 93.5
12. George Clooney – 93
13t. Benicio Del Toro – 91
14t. Josh Hartnett – 91
15. Chris Evans – 83.5
16t. Justin Timberlake – 82
16t. Ryan Phillippe – 82
18. Orlando Bloom – 81
19. Derek Jeter – 80
20. David Duchovny – 78.5
21. Owen Wilson – 77.5
22. Joe Jonas – 77
23. Ryan Reynolds – 75
24. Ashton Kutcher – 73
25. Jeremy Piven – 72.5
26. Ryan Gosling – 72
27t. Kanye West – 71
27t. Brad Pitt – 71
27t. Jude Law – 71
30t. Colin Farrell – 70
30t. Adam Levine – 70
32. Sean Penn – 69
33t. Taylor Lautner – 67
33t. Johnny Depp – 67
35. Jake Gyllenhaal – 66
36. Andy Roddick – 64.5
37t. Tom Brady – 64

37t. Mark Sanchez – 64
39t. Zac Efron – 63
39t. Adrien Brody – 63
39t. Adam Brody – 63
39t. Kevin Connolly – 63
43. Chris Pine – 62.5
44t. Michael Phelps – 62
44t. Adam Duritz – 62
46t. Alexander Skarsgard – 62
46t. Wilmer Valderrama – 62
46t. Gerard Butler – 62
49. Criss Angel – 61
50. John Mayer – 60
51. Bradley Cooper – 57
52. Shia LaBeouf – 56.5
53t. Alex Rodriguez – 53
53t. Will Smith – 52
55. Robert Downey, Jr. – 51.5
56. Edward Norton – 51
57. Paul Walker – 48.5
58. Matthew Morrison – 47

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