With all the commotion caused last week by rumors of Sean ‘Diddy’ Combs dating every man’s pretend girlfriend Kate Upton I though that this week we’d take a look at Diddy’s alleged dating history. As you will see from this list, it should come as no surprise to anyone that he could land a gorgeous woman like Kate. His dating history with the pretty and famous is impressive. But how does it compare to the other 49 men we’ve chronicled thus far? Read on to find out.

Photo credit: Sean Combs image by cinemafestival/Shutterstock

Salli Richardson (1990-1991)

Richardson and Diddy allegedly dated back in the day. I say allegedly because i don’t even think there was Internet when this took place.

Hookup score: 9.0
A 23 year-old Salli Richardson is a nice find.

Photo credit: Salli Richardson image by s_bukley/Shutterstock

Kim Porter (1996-1999, 2003-2007)

Porter and Diddy dated on-and-off for over a decade and had three kids together, one before the initial split and two after.

Hookup score: 9.0
Kim is quite the looker so it’s easy to see how he reconciled with her.

Photo credit: Kim Porter image by s_bukley/Shutterstock

Kimberly ‘Lil’ Kim’ Jones (1997-1998)

Again, I am not sure about this one, but it’s been reported that they went out so I guess we’ll count it.

Hookup score: 8.5
Sadly they had a falling out and are reportedly no longer friends.

Photo credit: Lil Kim image by Featureflash/Shutterstock

Jennifer Lopez (1999-2001)

This one definitely happened as it was prime celeb gossip fodder for a couple of years. Lopez was even with Diddy the night that his entourage got into a night club argument that ended in gun fire.

Hookup score: 9.5
Ah, love…

Photo credit: Jennifer Lopez image by s_bukley/Shutterstock

Emma Heming (2001)

Diddy posed with Bruce Willis’ current wife in a photo spread for a 2011 issue of Details magazine and reportedly it went from there.

Hookup score: 9.5
Another hot 23 year-old for Diddy.

Photo credit: Emma Hemming image by s_bukley/Shutterstock

Sky Nellor (2002)

Diddy was rumored to be cheating on Kim Porter with Sky at this time while he and Sky were on tour together.

Hookup score: 8.5
This isn’t the first list she’s made.

Photo credit: Sky Nellor image by s_bukley/Shutterstock

Naomi Campbell (2002)

Diddy and Naomi dated, but it didn’t last long. They’re still friends though!

Hookup score: 10.0
Models and singers. Models and singers.

Photo credit: Naomi Campbell image by Anton Oparin/Shutterstock

Cassie Ventura (2006)

Diddy signed Cassie to his Bad Boy label and rumors abounded that they were an item, even going so far as to report that they might have been engaged at some point.

Hookup score: 9.5
Models and singers. Models and singers.

Photo credit: Cassie Ventura image by Featureflash/Shutterstock

Noemie Lenoir (2007)

There were rumors that Diddy had an affair with the then-married French supermodel Lenoir.

Hookup score: 9.5
Rumors, schmumors, we’re giving it to him.

Photo credit: Noemie Lenoir image by Jaguar PS/Shutterstock

Sienna Miller (2007)

Combs was spotted entering a New York hotel one morning with Miller sparking rumors that they were an item.

Hookup score: 9.0
Finally someone other than a model or a singer.

Photo credit: Sienna Miller Image by Jaguar PS/Shutterstock

Aubrey O’Day (2007)

Combs and O’Day worked together on his reality show Making the Band in which her group Danity Kane were the winners. She claimed that their relationship was “strictly professional.”

Hookup score: 9.0
Sigh, another singer.

Photo credit: Aubrey O’Day image by Featureflash/Shutterstock

Cameron Diaz (2008, 2011)

Diaz and Diddy were caught kissing at a hotel in New York in 2011 after she had broken up with Alex Rodriguez. Apparently they also hooked up a few years earlier as well, according to reports.

Hookup score: 9.0
Yes, an actress again!

Other less-substantiated alleged flings: Alicia Douvall, Claudia Jordan, Karrine Steffans, Kendra Wilkinson

Photo credit: david_shankbone, Flickr

Final Tally

Sean ‘Diddy’ Combs’ Hookup Score: 110 points

And we have a new entrant in the Top 5! At just 43 years-old and with still plenty of game Diddy could make a run at Charlie Sheen for third before it’s all over.

1. Leonardo DiCaprio – 187 points
2. Jack Nicholson – 163
3. Charlie Sheen – 136
4. Sean ‘Diddy’ Combs – 110
5. Stephen Dorff – 109.5
6. Jamie Foxx – 108.5
7. Jared Leto – 108
8. Seth MacFarlane – 98
9. George Clooney – 93
10t. Benicio Del Toro – 91
10t. Josh Hartnett – 91
12. Chris Evans – 83.5
13t. Justin Timberlake – 82
13t. Ryan Phillippe – 82
15. Orlando Bloom – 81
16. Derek Jeter – 80
17. David Duchovny – 78.5
18. Joe Jonas – 77
19. Ryan Reynolds – 75
20. Ashton Kutcher – 73
21. Jeremy Piven – 72.5
22. Ryan Gosling – 72
23t. Kanye West – 71
23t. Brad Pitt – 71
23t. Jude Law – 71
26t. Colin Farrell – 70
26t. Adam Levine – 70
28. Sean Penn – 69
29t. Taylor Lautner – 67
29t. Johnny Depp – 67
31. Jake Gyllenhaal – 66
32t. Tom Brady – 64
32t. Mark Sanchez – 64
34t. Zac Efron – 63
34t. Adrien Brody – 63
34t. Adam Brody – 63
34t. Kevin Connolly – 63
38t. Michael Phelps – 62
38t. Adam Duritz – 62
38t. Alexander Skarsgard – 62
38t. Wilmer Valderrama – 62
38t. Gerard Butler – 62
43. Criss Angel – 61
44. John Mayer – 60
45. Bradley Cooper – 57
46. Shia LaBeouf – 56.5
47. Alex Rodriguez – 53
48. Robert Downey, Jr. – 51.5
49. Edward Norton – 51
50. Matthew Morrison – 47