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tameodesza · 5 months

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To All the Men Shawn's Ever Loved

Headcanon about Shawn’s dating history in some random AU in my head, lol. Inspired by this post by @piratewithvigor about Shawn and his 5 boyfriends 🤭

Marty: 7 years ―୨୧⋆ ˚

Shawn dated around a lot in his youth, but Marty was his first long-term serious relationship

They met at the start of their careers before teaming together in smaller promotions. Marty chased after Shawn rigorously, the blond being hard to get.

It wasn’t that Shawn didn’t find Marty attractive, but he’d made a promise to his brothers that he’d never date a wrestler. They didn’t have the best track record in relationships, and Shawn’s older brothers didn’t want him to get his heart broken. If only he’d listened.

Marty eventually won Shawn over with how sweet he was, and how interested he seemed to learn about Shawn rather than deducing him to just a pretty face. They took things slow and Shawn finally said yes to the idea of a relationship after Marty had kissed him after leaving a show.

Things were pretty good in the first few years, but the relationship eventually became super toxic, especially around the time Shawn began to gain more popularity and success than Marty.

But they still tried to make it work, Shawn more so than Marty, because of how long they’d been together. Shawn wasn’t willing to give up so easily on a man he considered the love of his life.

But love wasn’t enough to combat their constant relationship problems – trust issues, jealousy, fighting, cheating, etc.

After another pointless argument, Shawn had enough and asked for a break.

✦ . 　⁺ 　 . ✦ . 　⁺ . ✦. ✦ . 　⁺ 　 . ✦ . 　⁺ 　 . ✦.

Kevin: 3 years ―୨୧⋆ ˚

Shawn wasn’t used to being a single man, and after meeting Kevin, his “break” with Marty swiftly turned into an official breakup.

Shawn was attracted to Kevin the moment he saw him on WCW in that ridiculous Oz gimmick. When Kevin came to the WWF, everything just seemed to click between them. They got along well, Kevin didn’t care about the heat Shawn had backstage, and they seemed to have the same sense of humor with Kevin being just as goofy as Shawn.

Kevin had only been there for two weeks before they got together, Shawn determined to scoop him up before someone else could. Being with Kevin was the freest Shawn felt in ages. It was definitely an adjustment to go from his previous relationship to someone who was so laid back, gentle, caring, loving, and protective in a non-possessive way.

Kevin helped to build back up the confidence that Marty had torn down. He was the perfect man for Shawn and it should’ve been a perfect relationship. But in true Shawn Michaels fashion, nothing could ever be that simple.

Despite being with a man that treated him better, Shawn carried over the toxic traits he’d learned from his previous relationship with Marty and basically self-sabotaged his relationship with Kevin. Their problems usually stemmed from Shawn’s lies, jealousy, and trust issues. Which eventually progressed to him picking fights with Kevin just to get a reaction out of the man.

But Kevin was nothing like Marty, and he was too mature and level headed to fall for Shawn’s antics, which only seemed to make Shawn angrier. But Kevin had learned not to feed into the anger, knowing that Shawn would eventually cool off and apologize before crawling into his awaiting arms.

Their relationship reached a boiling point when Kevin told Shawn he was leaving for WCW. Shawn barely registered Kevin’s explanation before he was yelling at the man, saying he was selfish, that he was abandoning him, that Kevin didn’t love him and was only chasing after Scott.

That caused Kevin to lose his cool, his frustrations spilling over as he cursed out Shawn, offended that the blond would question his love for him and insinuate something between him and Scott. The argument ended with Kevin calling Shawn clingy, which was more of an honest observation than an insult, and Shawn telling him to go fuck himself. Who was Kevin to call him clingy? He’d show him clingy, alright.

That night sealed the fate of their relationship when Shawn did the unthinkable and cheated on Kevin with none other than the hitman, Bret Hart.

✦ . 　⁺ 　 . ✦ . 　⁺ . ✦. ✦ . 　⁺ 　 . ✦ . 　⁺ 　 . ✦.

Bret: 1 year ―୨୧⋆ ˚

My fav ship, but they don’t have a happy ending in this timeline 😭 (sorry hartbreak fans!)

Marty and Shawn’s relationship walked so Bret and Shawn’s could run, both men being equally as toxic but somewhat addicted to each other.

Their relationship had not-so-humble beginnings that spawned from Shawn’s infidelity. And what started from sex eventually grew into an unhealthy codependent relationship with both men using each other to fill some kind of void, Bret fresh from a divorce and Shawn still heartbroken from Kevin dumping him.

It may have been Shawn’s shortest relationship, but it was hands down the most intense relationship he’d experienced on so many levels.

The love was intense, both men love bombing each other as soon as they were official, quick to let everyone know the other was off limits. Bret specifically made it his mission to show excessive PDA with Shawn whenever Kevin was around, and he continued to do so up until Kevin left for WCW. Shawn was often unaware, just happy to receive Bret’s affection.

Their fights were intense, others often thinking the two would kill each other if someone didn’t step in. They’d gotten kicked out of hotel rooms on multiple occasions due to noise complaints or damage that had been done due to one of them throwing shit around the room. Many of their fights had centered around Kevin, Bret’s jealousy leading him to believe that Shawn was still in love with the man, and Shawn’s annoyance at Bret constantly bringing up his ex.

And best, or worst depending on how you look at it, was that the sex was intense. Shawn had been introduced to so many new kinks, toys, and sex positions because of Bret, and his orgasms were unlike anything he’d ever experienced, the blond often coming multiple times before Bret’s climax. Shawn found that the sex was best when they were mad at each other, thus beginning his unhealthy obsession with riling up Bret, leading to an explosive fight and the most erotic hate sex. It was almost as good as the passionate makeup sex that followed.

Overall, sex was really what kept each other coming back. But beyond their attraction, there wasn’t any substance to the relationship. They hadn’t learned anything important about each other like birthdays, favorite colors, likes/dislikes, etc., which one could say led to many of their arguments because they didn’t really have a good understanding of each other.

Shawn made the mistake many times of comparing Bret to Kevin because, honestly, he’d never gotten over the man. And deep down, he wished to work things out with him, but Kevin had made it very clear that he wanted nothing to do with Shawn after what he’d done.

So he settled for what he could get, but Bret wasn’t Kevin. He didn’t have Kevin’s patience and wasn’t one to tiptoe around his words to protect Shawn’s feelings.

But just like with his relationship with Marty, Shawn was hesitant to rip the band aid off despite how bad things had gotten between them. He’d grown accustomed to dysfunction, and he’d much rather put up with that than being alone.

The relationship only ended when Shawn got a taste of his own medicine. They say you lose him how you get him, and those words were never truer when Shawn found out that Bret had cheated on him with Sunny.

No surprise, the breakup was messy. Bret and Shawn had argued in front of the whole locker room, almost getting into a fight before Hunter and Chyna pulled Shawn away. But Shawn was a spiteful man and wasn’t going to let that be the last of it.

He keyed Bret’s car in the parking lot and threw a brick through the driver’s side window as an added bonus. Bret didn’t find out about it until the end of the show when leaving the arena. He was pissed and this led to him and Shawn actually fighting in the bathroom backstage the next week, Bret ripping out a few strands of Shawn’s hair in the process.

But Shawn got the last laugh in Montreal when Bret was screwed out of the WWF title.

✦ . 　⁺ 　 . ✦ . 　⁺ . ✦. ✦ . 　⁺ 　 . ✦ . 　⁺ 　 . ✦.

Undertaker: 4 years ―୨୧⋆ ˚

Shawn was as a broken man after his breakup with Bret, and even more so after the screwjob. Aside from DX, no one in the locker room wanted anything to do with him regardless of him telling people he wasn’t involved in screwing Bret out of the title (a lie no one believed).

It was the loneliest he’d felt in some time and certainly the longest he’d gone being single, which he had a hard time dealing with. Being the third wheel of Hunter and Chyna certainly didn’t help.

Undertaker had gained the same disdain towards Shawn as many of the guys had after the screwjob, steering clear of the blond at all costs. But he was also a professional and was willing to put his pride aside to do his job. So when Vince came to him about a possible feud with Shawn and a casket match, Undertaker agreed to it, albeit begrudgingly.

Ironically, their relationship began after Undertaker had injured Shawn’s back on that casket.

He felt absolutely devastated after hearing of Shawn’s upcoming back surgery that was a result of the casket clipping his back. When the words ‘career-ending injury’ began floating around, he felt sick to his stomach from guilt, blaming himself for the accident.

After Shawn’s surgery, Undertaker sent numerous ‘get well soon’ cards and flowers to Shawn’s hospital room. Shawn initially thought it was from his family or Hunter, but the cards never identified a sender. It wasn’t until Undertaker visited him in the hospital, the only wrestler outside of Shawn’s friends to come see him, that everything came together.

Undertaker was expecting to receive anger, insults, a spew of curses, anything other than the appreciative smile Shawn gave him when he sat at his bedside. The conversation was light, pleasant even, ending with Shawn telling Undertaker not to blame himself for his injury. He didn’t blame him, so the dead man shouldn’t do the same.

The visits became more frequent and once Shawn was released from the hospital, Undertaker had even taken some time off the road to look after Shawn in Texas. It was during that time at Shawn’s home that they officially got together.

Being with Undertaker was vastly different than Shawn’s previous partners. It was almost a bit odd being with a man that was so thoughtful, yet also not afraid to call Shawn out on his shit. Undertaker had a very no-nonsense demeanor that Shawn respected and was drawn to.

At that point in his life, Shawn was done playing games, no longer interested in the drama of relationships. He didn’t want to pick fights or throw hissy fits. He wanted something easy. Simple. And that’s what they had.

During his time with Undertaker, Shawn had matured the most. Undertaker helped him better understand his emotions, reflect on his past, and realize what wanted in life going forward. It may have also helped that Shawn was completely sober due to him taking medication, which Undertaker made sure he wasn’t misusing.

Undertaker was very instrumental in helping Shawn train to go back to the WWF, now WWE, in 2002. A lot had changed in Shawn’s absence, and he was honestly insecure and a little bit scared to return. He didn’t know if the fans would even care about him returning. And he knew a few of the boys backstage wouldn’t be happy. But Undertaker was always there to kiss away his worries, ensuring him that everything would be ok. They would be together, and he wouldn’t let anything bad happen to Shawn.

Shawn didn’t know their relationship could get any stronger, but it surely did after his return to the company. For the first time, Shawn was able to see what it was like to have a healthy relationship on the road. Undertaker didn’t question him of his whereabouts backstage or hover over him at the bar. He trusted Shawn and Shawn trusted him, knowing that they’d always end the night in each other’s arms at the hotel.

They broke up some time in 2004. The breakup was amicable, and there were no cars keyed in the parking lot this time. Shawn wanted to take some time to focus on himself and his career, which Taker completely understood as they’d both been putting their career over their relationship. Undertaker also needed to focus on his own personal issues, especially with his brother Kane. As much as he didn’t want to admit it, it was best for Shawn’s safety for them to be apart for the time being.

As mutual as the decision was, it was still a painful breakup for the two. They really loved each other, and always would, but they had their own paths in life that didn’t seem to involve each other at the moment. They figured if it was meant to be, they’d find each other again.

✦ . 　⁺ 　 . ✦ . 　⁺ . ✦. ✦ . 　⁺ 　 . ✦ . 　⁺ 　 . ✦.

Hunter: 2006 - Present ―୨୧⋆ ˚

To be honest Shawn should’ve seen this one coming.

Hunter had been Shawn’s best friend since 1996. He thought Shawn was the most beautiful man he’d ever seen when he first met him, and he’d almost made a move on the blond until he learned that Shawn was dating Kevin. Hunter settled on being good friends with Shawn and began dating Chyna shortly after.

As he and Shawn grew into best friends, his interest in the shorter man never wavered. Unfortunately for him, he never had an opportunity to pursue Shawn in their younger years as either he or Shawn always seemed to be in a relationship while the other was single.

And the one time that they were both single, they weren’t on speaking terms. They’d gotten into a heated argument where Shawn called Hunter a backstabbing friend and accused him of using him to get to the top. Hunter was fed up with taking the brunt of Shawn’s anger and they both didn’t speak to each other for over a year after that.

Surprisingly, it was Kevin that reunited the two, encouraging Hunter to talk to Shawn and hear him out. After hearing about Shawn’s injury and back surgery, Kevin was quick to call the blond, concerned about his well-being. Though they hadn’t ended on good terms, he would always care for him.

They’d kept in touch sparingly since then and through their short conversations, Kevin learned of Shawn’s falling out with Hunter. Shawn was a stubborn man and Kevin knew that no matter how sorry Shawn sounded over the phone, Hunter would need to make the first move to fix their friendship. And after learning how sorry Shawn was, that’s what Hunter did.

He still held a bit of anger towards Shawn, but he missed him. And after a tearful reunion, their friendship was back even stronger, and so was his feelings for the blond. Feelings that had never left. But Hunter soon learned it was too late to pursue anything as Shawn had been dating Undertaker.

So just as he had in 1996, Hunter settled on being a good best friend to Shawn. And he was ok with that. They had so much to catch up on, and Hunter was just happy to have his buddy back.

Shawn and Hunter didn’t get together until 2006 after DX reunited. They’d already been close after rekindling their friendship but being DX once again and constantly being surrounded by each other while also never getting sick of the other really solidified their feelings for one another. That and the kiss Shawn gave Hunter on New Year’s Eve.

For the first time, Shawn felt confident as he went into his relationship with Hunter. He was in a better headspace, had matured, and instead of carrying over toxic traits of past relationships, he carried over the lessons he’d learned over the years, determined to make this relationship last because he not only cared for Hunter as a lover but as a best friend. He’d already built up an immense amount of love for the man, and he didn’t want to ruin their relationship again. Also, Shawn was getting up there in age and was ready to settle down.

Being with Hunter made Shawn wish he’d made the decision sooner. They just got each other. Many times Shawn wouldn’t need to say anything, just give Hunter a look and the man would know what he was thinking.

Hunter was always so tender with him, probably afraid that Shawn would break or revert to his old ways at the slightest hiccup, which Shawn wasn’t going to allow to happen.

Shawn loved that Hunter was very affectionate, always touching him in some kind of way whether it’s holding his hand, hugging him every chance he got, playing with his hair, or tugging on his pocket to bring him closer.

Their fights were minimal, or at least they fought the least out of any of Shawn’s relationships. But when they did fight, it wasn’t the usual screaming matches Shawn was accustomed to. They talked to each other calmly with level heads, both hearing each other out before making a point. And they’d always end the conversation with a hug and an ‘I love you.’

Shawn’s sure Hunter’s the one after the man gets injured in 2007. Seeing Hunter in the hospital in so much pain and not being able to do anything about it broke Shawn.

He took time off the road to help Hunter with his injury, much like Undertaker had done for him. Being with Hunter every day so close in such an intimate setting of Hunter’s Connecticut home made Shawn realize he wanted to spend the rest of his life with him. And any man that could make Shawn endure the cold Connecticut winters deserved his heart.

The proposal was impromptu, Shawn whipping out the ring after Hunter’s physical therapy session. It was bittersweet, more sweet than bitter, since Hunter wanted to be the one to propose first. He’d been planning on doing it and would have done it sooner had it not been for his injury.

But as he looked into Shawn’s beautiful teary blue eyes, he said yes, of course, and they were married on New Year’s Eve of that year, sharing the same kiss that started their relationship.

Looking back on the past, as painful as it was, Shawn wished he could thank all of the men he’d ever loved for teaching him how to love and helping him grow into the husband he was today.