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Grappling Casanovas: 15 Wrestlers Who Dated More Than One Diva

It’s no surprise that many men in the business of professional wrestling do pretty well for themselves when it comes to meeting women. After all, these athletes have fame, fortune, and also spend more than their fair share of time in the gym. They also have access to some of the most beautiful women in the world, working with and around gorgeous female wrestlers and valets.

Of course when you have a group of attractive men and women spending a significant portion of time together, one can reasonably assume a few romantic connections will occur and this assumption would indeed be correct.

However, there are some wrestlers that have been fortunate enough to have dated more than one of the lovely females involved in sports entertainment. In fact, many of these athletes have dating resumes that most men (especially wrestling fans) would envy.

There are some pairings in the this article that folks might be aware of and also more than a few that only the most diehard wrestling fans will know about. The list includes some of most well known wrestlers in the history of the sport.

So let’s take a look at 15 wrestlers who dated at least two different female talents during the course of their careers.

15 CM Punk

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CM Punk won over wrestling fans with his impressive skills in the ring and on the mic. The two-time WWE Champion retired from wrestling in 2014, in order to pursue a career in mixed martial arts. His current MMA record stands at 0-1 following a submission loss to Mickey Gall back in 2016.

Punk might have the most impressive dating resume of any wrestler on the planet. He has been previously involved in relationships with WWE Hall of Famers Lita and Beth Phoenix. He has also dated current WWE star Maria Kanellis. Moreover, Punk has been romantically linked to TNA wrestlers such as Traci Brooks and Daffney. There were also rumors circulating at one point that the Chicago native and Kelly Kelly were an item. Today he appears to have settled down and is currently married to former WWE Divas Champion AJ Lee.

14 John Cena

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John Cena has been a top draw in the sport of professional wrestling for well over a decade. He has headlined numerous WrestleMania cards and is arguably the biggest name in sports entertainment today. Cena is also a 16-time World Champion.

Even the most casual wrestling fan likely knows that John Cena proposed to Nikki Bella at WrestleMania 33 and that the two have dated for quite some time. However, Cena has also been linked to several other past and present WWE employees. Apparently, the former champ had previously been involved with current WWE star Mickie James. The Massachusettes native has also been romantically linked to former WWE Diva Victoria way back in 2002. There have also been unsubstantiated rumors linking Cena to wrestlers like Kelly Kelly and Maria Kanellis over the years.

13 Matt Hardy

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Matt Hardy is one-half of the legendary tag team known as The Hardy Boyz. He has held tag team gold in virtually every promotion he has competed in. He has also had a successful career as a singles competitor and has held the ECW Championship and the TNA World Heavyweight Championship. Hardy recently had a bit of a career resurgence by portraying the character known as “Broken” Matt Hardy on Impact Wrestling, which resulted in him and his brother Jeff being re-signed by WWE.

Hardy was involved in a high-profile relationship with former Women’s Champion Lita. The two dated from 1999 to 2005 before Lita began dating “The Rated R Superstar” Edge. Hardy also dated former Diva Search winner Ashley Massaro, who worked with the company from 2005 to 2008.These days, Hardy is married to wrestler Reby Sky. The couple recently welcomed their second child in June of 2017.

12 Zack Ryder

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The former self-proclaimed “Internet Champion,” Zack Ryder, has had his share of success while working for WWE. He is former United States Champion, Intercontinental Champion, and was even a former Tag Team Champion. He currently wrestles as a member of the tag team known as The Hype Bros with his partner Mojo Rawley, though current storylines suggest they may be teasing a breakup and feud.

Zack Ryder dated Australian wrestler Emma for most of 2016. However, the two recently separated sometime around last November. Apparently, Ryder moved on rather quickly and began dating Impact Wrestling’s Laurel Van Ness in April of 2017. It would appear that Ryder may have a thing for blonde female wrestlers in their 20s. Ryder may not be the biggest star in WWE at the moment, but he still seems to be doing alright with the ladies.

11 Dolph Ziggler

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Two-time WWE World Heavyweight Champion Dolph Ziggler is known for being one of WWE’s top in-ring performers. He is a former Money in the Bank briefcase holder who has also won both the WWE Intercontinental Championship and the United States Championship. Fans may also remember him as a member of the all-male cheerleading stable known as The Spirit Squad when he performed under the ring name Nicky.

Dolph Ziggler is known to have dated Total Divas star Nikki Bella from around 2008 to 2011, though the exact timeline isn’t known. In an episode of Total Divas that aired back in 2015, Ziggler even claimed we still had feelings for Bella who didn’t seem to share the sentiment. Ziggler also dated fellow wrestler Dana Brooke for a brief period in 2016.

10 John Morrison

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The winner of Tough Enough Season 3 went on to make quite a name for himself in WWE. He began his career with the company performing under the ring name Johnny Nitro as a member of the tag team/stable known as MNM. He went on to perform as a singles competitor and became John Morrison. During his almost six years in the WWE as a member of the main roster, he won various title, including the ECW World Championship. He currently competes in the upstart promotion Lucha Underground as Johnny Mundo.

Morrison dated former WWE Diva Melina (Perez) for about 12 years before calling it quits in 2015. These days he is currently involved with his Lucha Underground co-star Taya Valkyrie. In fact, as of June 2017, the two are officially engaged.

9 Triple H

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Triple H has headlined WrestleMania on seven separate occasions. He is also a 14-time World Champion and was one of WWE’s biggest stars during The Attitude Era. These days the former D-Generation X member officially holds the title of Executive Vice President of Talent, Live Events, and Creative for the company while working primarily behind the scenes.

Triple H is married to Stephanie McMahon, the daughter of WWE CEO Vince McMahon. They have been a couple since 2000. The two actually started dating while portraying a couple on-screen as fiction eventually became a reality. Before his relationship with McMahon, Triple H dated his fellow D-Generation X stablemate Chyna for several years. In fact, Chyna even served as his bodyguard/valet during the early part of his career in the WWE.

8 "Macho Man" Randy Savage

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The “Macho Man” Randy Savage was one of wrestling biggest stars in the 1980s and 90s. He is arguably best remembered for his feuds with Hulk Hogan and his legendary match with Ricky Steamboat at WrestleMania III. Savage was a two-time World Heavyweight Champion and also held the Intercontinental title.

During a good portion of his career in WWE, Savage was accompanied to the ring by Miss Elizabeth (Hulette) who was his wife behind the scenes. Hulette was actually introduced to the wrestling business by Savage, and she became a legendary figure in her own right. Toward the end of his career, in the late '90s, the former world champ was involved in a relationship with his blonde valet known as Gorgeous George (Stephanie Bellars) whom he also brought into the business.

7 Alberto Del Rio

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Alberto Del Rio or Alberto El Patron for the Impact Wrestling Fans out there is the current Impact Wrestling Champion. However, he is probably better known for his time in WWE where he was able to capture the WWE Championship and the WWE World Heavyweight Championship (twice). He also held the WWE United States Championship on two separate occasions.

In 2016, the wrestling rumor mills were swirling with allegations that suggested that Del Rio was involved in a love triangle with Charlotte Flair and his current girlfriend, Paige. However, the exact nature of Del Rio’s relationship with Flair isn’t clear, though they are believed to have been romantically linked for a short period before Del Rio and Paige became an item. The Mexican superstar is currently engaged to former Divas Champion, Paige.

6 Edge

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The Canadian wrestler known as Edge had an eye-popping 31 title reigns during his time in the WWE. He is best known for his reigns as a World Heavyweight Champion and for teaming with his tag partner Christian. In 2012, Edge was inducted into the WWE Hall of Fame.

Edge was involved in a relationship with fellow WWE Hall of Famer Lita back in 2005. At the time, Lita was dating another wrestler, Edge's friend Matt Hardy. The love triangle was actually turned into a moderately successful on-screen storyline involving the three superstars. The relationship didn’t last long, and Edge and Lita drifted apart sometime in 2006. Edge would eventually settle down with another WWE Hall of Famer Beth Phoenix. The two were wed in 2016 and have two daughters together.

5 Randy Orton

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Third-generation superstar Randy Orton has certainly had a Hall of Fame worthy Career in World Wrestling Entertainment. Orton is a 14-time World Champion and has been one of the most popular performers in the company for well over a decade. Moreover, Orton has also headlined WrestleMania XXV and WrestleMania XXX.

Randy Orton is another wrestler whose romantic exploits are often the subject of rumor. He has admitted to being involved with former WWE Diva Kelly Kelly. There was also gossip in wrestling circles that Orton dated wrestler Mickie James some years back. The relationship (if there even was one) between James and Orton has never been confirmed. Moreover, Orton was also romantically linked to WWE ring announcer JoJo Offerman back in 2013, based largely on a photo of the two being posted on the internet. The evidence that Orton and Offerman were an item is flimsy at best.

4 Davey Richards

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Davey Richards has been featured prominently in Impact Wrestling over the course of recent months. He is probably best known for being one-half of The Wolves (or The American Wolves) with his former partner Eddie Edwards. He has held the TNA World Tag Team Championship on five separate occasions and is also a former Ring Of Honor World Champion.

Richards has been previously married to an independent professional wrestler who performed under the ring name Christie Summers. Summers and Richards were married in 2008 and separated sometime around 2010. In 2015, Richard began dating six-time TNA Knockouts Champion Angelina Love. The two announced their engagement in April of 2015. Moreover, Love gave birth to their first child in March of 2016.

3 Paul London

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Longtime WWE fans will likely remember Paul London as a member of the tag team collectively known as London and Kendrick. He and his then-partner Brian Kendrick are former WWE World Tag Team Championship. The pair won the titles back in 2006. London has also held the WWE Cruiserweight Championship as a singles competitor. These days he can be seen on Lucha Underground as the leader of “The Rabbit Tribe.”

Paul London dated Impact Wrestling’s Angelina Love some years back but the details regarding their relationship are scarce. He also dated former WWE Diva Ashley Massaro around 2007. His dating Massaro apparently caused some heat between himself and her former boyfriend, Matt Hardy. London and Massaro called it quits in 2008; the two were both released from WWE the same year.

2 Shawn Michaels

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Shawn Michaels is considered by many fans and insiders to be one of the best in-ring performers to ever set foot inside a pro wrestling ring. His matches against the likes of Bret Hart and The Undertaker are considered to be among the best matches in WWE history. Michaels was inducted into the WWE Hall of Fame in 2011.

Shawn Michaels is known to have hooked up with former WWE Diva Sunny way back in the late 1990s during the height of her popularity. He would also been romantically linked to WCW Nitro Girl Whisper. In fact, Michaels would even go on to marry Whisper, whose real name was Rebecca Curci. The two have been married since 1999 and have two children.

1 Tommy Dreamer

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Tommy Dreamer had a very respectable career in WWE. In fact, Dreamer is the only wrestler to hold both the WWE version of the ECW Championship as well as the original. The “Innovator of Violence” has also held the WWE Hardcore Championship. That being said, Dreamer arguably reached the height of his popularity in the 1990s as a member of the original ECW roster.

During his days in Extreme Championship Wrestling Dreamer became involved in a relationship with “The Queen of Extreme” Francine (Fournier) who was his on-screen manager briefly in the late-'90s into the early-2000s. He also dated another ECW alum, Beulah McGillicutty, whom he would eventually wed. Dreamer and McGillicutty have been married since 2002 and even have twin daughters together.

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Grappling Casanovas: 15 Wrestlers Who Dated More Than One Diva