Life on the road can be difficult regardless of why one lives it. Beyond the hardships involved in simply living everyday life at hotels and airports, it can also be exceedingly difficult to maintain any sort of romantic relationships while constantly traveling. Professional wrestlers definitely understand this plight, with family problems being notoriously endemic throughout the industry. To combat this problem, romances within the industry have also become highly en vogue, but naturally these relationships are as susceptible to falling apart as any other, and thus don’t always last.
Given how many times wrestlers need to fall down and get back up, it goes without saying they live the mantra “if at first you don’t succeed, try again.” It therefore makes sense that one bad relationship wouldn’t cause a wrestler to give up on dating their coworkers altogether. In fact, most wrestlers who dated one of their female counterparts are bound to make a habit of it, giving the impression that the pros of the practice far outweigh whatever bad memories surround the inevitable breakups.
Wrestlers dating one another has occasionally caused problems backstage for both the people in the relationship and the others they worked with at the time, but there has never been any major rule against the concept in general. This could owe to the fact a large number of the most serial daters in wrestling have also been amongst the most powerful men in the business, which might also explain why they find it so easy to attract the gorgeous women of the WWE Universe. Keep reading to learn about 15 male wrestlers you never knew dated multiple divas.
15 The Undertaker
As the saying goes, certain chicks just dig jerks, so it tracks they would also downright adore Big Evil. The first female wrestler to show her affection to The Undertaker was more of a technicality, considering she only ever started making appearances in the WWE Universe because she and the Dead Man were already dating. Undertaker and Sara Gilbert got together in 1999 and were engaged by the time the Phenom turned into The American Bad Ass. Despite her lack of acting skills, Sara started getting involved in Undertaker’s storylines for a few months throughout 2001, most notably his feud with “Diamond” Dallas Page. The marriage produced two children, but was apparently even rockier than the storyline, ending in divorce seven years later. Not long after that, Undertaker began a relationship with female wrestler/model Michelle McCool, who was winding down her career after two reigns each as Divas and Women’s Champion. Undertaker and McCool were married in 2010 and had their first child in 2012.
Modern relationships being what they are, it might not be accurate to claim every relationship on this list necessarily constituted two wrestlers “dating.” Raven in particular may not have ever “dated” any of his female coworkers, but if the rumors are to be believed he certainly slept with a large number of them, starting with just about every one of his valets. The one woman we can be sure Raven never dated was Becky Bayless, although he did admit to her winding up in his hotel room one night when she was a 15-year old fan. Nothing happened, though – Raven was dating Joel Gertner’s wife at the time, and a bitter Gertner basically tried to frame him with Bayless as revenge. Outside of Gertner’s wife, there was also a confirmed relationship with Missy Hyatt, plus rumored flings with Beulah McGillicutty, Francine, Chastity, and Kimona Wanalaya, all implying Raven helped them get their ECW jobs through the relationships. Chances are this is an exaggeration of their friendships at best and sexist speculation at best, but given Raven’s general disposition, that doesn’t mean he didn’t have some relations with a few of the ladies along the way.
13 Alberto Del Rio
Thanks to social media, it's possible that Alberto Del Rio is on his way to being better known for his relationships than his long and impressive career in WWE. Multiple World Championships aren’t as scandalous or interesting as leaving his job behind for a life of partying with his younger girlfriend Paige, especially coupled with the rumor said relationship with Paige started when Del Rio cheated on his previous girlfriend, Charlotte Flair. While the Del Rio-Charlotte relationship was never as public as his current affair with Paige, it still managed to cause a stir backstage when it ended in a love triangle, only usurped by the ongoing antics of Paige and Del Rio after he left the company. Throughout it all, Del Rio has also been married to a third woman, Angela Velkei, who is also the mother of his three children. Del Rio claims the relationship with Velkei ended in 2015, though she didn’t file for divorce until his antics with Paige became well known.
12 Dolph Ziggler
Thanks to a certain trainwreck of a relationship with a famous comedienne, Dolph Ziggler will never again have trouble attracting a certain athletic type of lady. Female wrestlers are definitely capable of keeping up with his calisthenic lifestyle, most famously including Nikki Bella thanks to her later high profile relationship and reality show. Ziggler was also alleged to have had a brief fling with Kelly Kelly, the only person specifically named by Randy Orton to have done so when he made questionable comments about Kelly during a radio interview. More recently, Ziggler has apparently turned his affections to one of the latest female NXT call-ups, Dana Brooke. While the alleged couple has never made any public statement on the matter, Twitter and Instagram posts certainly paint the picture of possible romance between the two. Showing the downsides of interoffice romances, Brooke has already been accused of trying to “sleep her way to the top,” although if that were the plan, she probably would’ve aimed higher than Ziggler.
You may think you know Edge, but chances are so did his two ex-wives, plus the woman he had an extremely high profile relationship with concurrently with the ending of that second marriage. That he currently has a third wife means there’s probably a fourth woman who thinks she knows Edge, as well, and she may be right, as the first woman to give him children. Edge’s current wife is Beth Phoenix, whom he started dating around 2011 after his career was suddenly cut short due to severe neck injuries. Edge’s previous two wives were unconnected from the business, aside from the fact his first was Val Venis’s sister. More famously, between his second and third marriage, Edge engaged in a very public romance with Lita, who started the relationship by cheating on Matt Hardy. Edge was also cheating on his wife at the time, causing a huge public stir, and yet also leading to his greatest exposure in the ring.
10 “Macho Man” Randy Savage
One of the most iconic workers in wrestling history no matter how you slice it, the success of “Macho Man” Randy Savage and Miss Elizabeth’s relationship is probably the reason so many other wrestlers were willing to give the idea a go. Not the way the two acted, of course—Savage was the worst husband imaginable, both onscreen and off. He made boatloads of money, though, and created one of the most memorable acts in WWE history, showing the benefits of real life couples working together in tangible terms. Based on the past success, years after Savage and Elizabeth were divorced Randy tried to replace her in WCW with his new girlfriend, Stephanie Bellars, renamed Gorgeous George. Introducing a buxom blonde less than half his age as his new lady didn’t exactly make Savage look cool, rather making him look like he was suffering a midlife crisis, and the pairing didn’t last long either in the ring or in real life.
9 Matt Hardy
Quite a few of the stories on this list end in relative happiness, at least for now, so there’s no blaming these superstars for having no regrets about their dating life. However, considering how the concept has worked out for Matt Hardy on a personal level, it’s still a little surprising that he specifically would keep with the practice until it finally worked. His first two relationships were both highly tumultuous, both ending in shattered friendships. First there was Lita, who cheated on him with Edge. As if that wasn't bad enough, blogging about the ordeal temporarily cost Hardy his job. Matt rebounded with 2005 Diva Search winner Ashley Massaro, and though their relationship ended reasonably normally, their breakup caused Hardy’s friendship with Paul London to shatter when London and Massaro started dating before Matt was ready to move on. Nowadays, Hardy is married to Reby Sky, who he met in 2011 one month before she made her in-ring debut for Lucha Libre USA. Sky has since followed Hardy to TNA and other independents, presumably staying away from Hardy’s friends while doing so.
8 Tommy Dreamer
Heralded as a pretty boy upon his arrival to ECW, it didn’t take long for Tommy Dreamer to shed that reputation and instead earn regard as the Innovator of Violence. However, the fact Joey Styles was no longer lauding his boyish good looks in no way stopped women from taking notice of Tommy, most importantly his future wife Beulah McGillicutty. While most fans probably assume Dreamer and Beulah were together from the moment their storyline in ECW began to the present, the two actually had no interest in one another when they first met, at least not beyond a professional one. By the time Beulah left ECW to return to school, Dreamer was reported as dating Francine, and had no particular interest in his future wife’s departure. The full story has never been told, but what we know for sure is that Dreamer and Beulah reconnected some point after his relationship with Francine ended, and the two were eventually married in 2002.
7 Eddie Gilbert
Nicknames like “Hot Stuff” don’t come easy, and Eddie Gilbert earned the moniker by becoming on of the earliest examples on this list. Gilbert came to prominence throughout the mid 1980s wrestling for various southern territories, most notably the CWA in Memphis and the Mid-South promotion run by Bill Watts. Both a wrestler and a manager, Gilbert extended his reach by forming Hot Stuff Incorporated, a stable of wrestlers who served as his clients and tag team partners, all serving his nefarious means. He started dating fellow manager Missy Hyatt in the late 1980s, changing his organization’s name to “Hot Stuff & Hyatt International, Inc.” and eventually marrying Missy in 1987. The marriage didn’t last long, ending in divorce in 1989. Gilbert almost instantly rebounded with legendary female wrestler Madusa, who he married in 1990, though that relationship was even shorter. Interestingly, short relationships ran in Gilbert’s life whether professional or romantic, as his career was marked with brief and explosive tenures in a number of different companies. The prevailing wisdom often held he could have been a big star if he were only willing to stick in one place, and the same may well have been true for his love life.
6 “Stone Cold” Steve Austin
For all of the Texas Rattlesnake’s unmatchable accomplishments as a sports entertainer, when it comes to relationships, it would probably be more suitable to use his other nickname, the Bionic Redneck. Austin is currently in his fourth marriage, and though things are looking fine for him and his wife today, at least two of his exes aren’t particularly fond of their time together. He cheated on his first wife to pursue his second, who also happened to be the ex-wife of his trainer, Chris Adams. Showing a strong understanding of his student from the start, it was Adams who introduced Austin to Lady Blossom, initially as his valet. Despite their past, Adams apparently never had any trouble with Austin and Blossom’s marriage, using it to their advantage during an early feud in USWA. Blossom followed Austin to WCW until she retired due to her first pregnancy. They stayed together as Austin jumped to WWE, and it was in fact Blossom who came up with the iconic “Stone Cold” nickname. That wasn’t enough to keep their romance alive, though, and the couple divorced in 1999. Austin then married former WWE Women’s Champion Debra in 2000. The couple later divorced in 2003 after a domestic violence incident the year before.
5 Shawn Michaels
Only a certain type of man can get away with calling himself a sexy boy who ain’t no boy toy, especially in the WWE Universe, and a big part of the equation is having women willing to vouch for him when he says it. Technically speaking, Michaels has a less lengthy dating resume than some of the other athletes on this list, and chances are casual fans will only remember one of his two famous flames. During his time on top of the world as WWE Champion in 1996, Michaels was also living the boyhood dream behind the scenes, dating future WWE Hall of Fame manager and valet, Sunny. The relationship was volatile from the start, fueled by their respective drug dependencies and hurting many friendships along the way. After things with Sunny fell apart and Michaels life started spiraling into drug use, he asked Kevin Nash to introduce him to Rebecca Curci, better known to WCW fans as Whisper of the Nitro Girls. Like most Nitro Girls, Whisper didn’t do anything particularly noteworthy, at least until she left sports entertainment behind to marry HBK in 1999.
One of the most prolific lotharios in WWE history, Batista was rumored to hook up with just about every single female working for the company during his run on the top of SmackDown. Prior to even entering the wrestling business, Batista had already gone through one divorce and was in the middle of a second marriage, which started going south when Batista was constantly on the road. The Animal filled the romantic void in his life through flings with Melina, Kelly Kelly, Rosa Mendes, and possibly others. Throughout it all, he remained close friends with his second wife, albeit not close enough to prevent divorce, splitting in 2006. Whenever questioned about his dating habits, all Batista could say in his defense is that WWE hires the most beautiful women in the world, and to be fair, it’s a hard argument to beat. Batista might have found his own retort, though, by marrying a competitive pole dancer in 2015. The marriage has even survived Batista’s latest return to WWE, and thus working with female wrestlers, so she may just be the one.
3 John Cena
As the face of WWE, more women have laid eyes upon John Cena than any other modern performer, and from the looks of it, they like what they see. Even before Cena was a superstar, he dated Victoria when the two were up and coming stars learning the ropes in OVW. The relationship later became a point of controversy when Kenny Dykstra alleged Cena was dating a number of his female coworkers at the same time, though Victoria later denied this, pointing out their fling was brief and much earlier than Dykstra claimed. The point of the accusation was that Dykstra believed Cena was also in a relationship with Mickie James, which has never been officially confirmed by either party. Definitely confirmed and at a much higher profile than either of his former flames, Cena is currently in a long-term relationship with Nikki Bella. As fans of Total Divas are well aware, the couple have no immediate plans of marriage due to Cena’s previous divorce to a fourth woman unconnected to wrestling, Elizabeth Huberdeau.
2 CM Punk
Dropping a pipe bomb attracts all sorts of attention, and plenty of women have liked the cut of CM Punk’s jib enough to drop three word pipe bombs to him like “I love you.” They may not all have gone so far, but each of Punk’s past wrestler girlfriends no doubt shared some sort of affection for him during their time together, no matter how long things lasted. There were short flings with Maria Kanellis and Kelly Kelly during his runs in OVW and ECW respectively, an on-again-off-again relationship with Lita from 2011 to 2013, and another short stint with Beth Phoenix during the “off-again” phase, all before his current marriage to AJ Lee. Of all his relationships, Lee seemed the most integral to his career from the start, or perhaps we should say end, as it was her advice that lead Punk to seek out a second opinion after WWE doctors ignored his complaints. Had Punk and AJ never met, he may still be wrestling today. However, he could also be seriously hurt or worse, and might not be as happy, so we bet he’d keep things they way they are.
1 Triple H
All of the men on this list are lucky in one way or another to have dated some of the most beautiful and talented women ever to enter the WWE Universe. Luck doesn’t even begin to cover what Triple H fell into by successfully wooing Stephanie McMahon, thus gradually ensuring he would inherit her father’s company. While that hasn’t quite happened yet, the process is well underway, starting way back in 1999 when the two were paired together onscreen. Triple H was still dating Chyna at that point, but he didn’t let that stop him from romantically pursuing Stephanie for real, openly flirting with her while filming segments and causing the relationship to bleed into real life. The benefits for Triple H were immediate and obviously, only growing when the relationship blossomed into a marriage that has since lead to three children. Triple H is just as close with Stephanie’s father and family as he is with his wife, and the McMahon’s couldn’t be happier for it. As for Chyna? Let’s just say not all stories have happy endings, especially not when your ex is powerful enough to block you from the Hall of Fame.
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