AN: I have no idea where this came from. I blame writing The Stone-Hearted Queen, the approach of Valentine's Day (when I was writing this), Mac's honestly tragic love life and my running Iron-Dog joke and thus comparing Mac to Tony Stark in Just My Luck. Title comes from the song Cinderella from Disney's 1950 version and the summary is based off the Avengers quote ('Genius. Billionaire. Playboy. Philanthropist.'). I also have to give a very special shout-out to Dlwells51, who partly inspired this with a review on Forgive and Forget.

This is, I suppose, a MacGyver take on Cinderella, though it is probably less of a re-write of a fairytale as The Stone-Hearted Queen and not just due to setting. I mean, obviously, Mac is the Prince and Beth is Cinderella, but there's no evil stepmother or stepsisters and exactly who the Fairy Godmother is is probably up for debate…you'll see!

It also borrows a little, tiny bit from One Thousand and One Nights, though there is no execution and Mac has not gone the way of the Sultan, I promise! I think you'll see what I mean…

SEPTEMBER 2017

STUDIO OF A POPULAR TALK SHOW

LA

The extremely beautiful, blonde-haired, green-eyed young woman, in a designer dress and heels, smiled at the host, and then stood up and faced the camera.

'He's a billionaire, a genius, a philanthropist, a war hero and he looks really yummy in a tux…please welcome Cosmopolitan's 2017 Bachelor of the Year, Mr California, the owner of Jackson Industries, Angus MacGyver!'

Backstage, wearing a tux (which was really uncomfortable and clashed with the grease under his nails - metaphorically speaking, there was no grease today), Mac sighed internally and plastered on his best media-engagement smile, then walked out into the bright lights.

I did not even enter this Bachelor of the Year contest.

But, apparently, I'm rich and consequently famous enough that I don't get a say in the matter.

Seriously.

It'd be bad PR if I were to refuse to appear or participate in the contest, so, here I am…

Honestly, I live in California. I'm still wondering how I beat out all the bachelors in Silicon Valley and Hollywood to even be the California nominee in the first place…

He gave a jaunty wave to the studio audience, then made his way to the centre of the stage to greet the host and the Cosmopolitan representative.

JUNE 2018

MACGYVER'S PENTHOUSE

JACKSON TOWER

LA

'I'm really happy for you.'

Mac smiled, fond, happy and completely genuinely, and reached out and put an arm around Jack's shoulders, as the two of them sat by the fire-pit on the large balcony recessed into the side of the Tower, drinking ice-cold beer from Mac's walking, self-opening Esky.

Jack had been lonely in a way that Mac and the rest of his friends, as much as they loved Jack and he loved them, couldn't help with.

Honestly, part of Mac had feared that Jack would never develop another special, meaningful connection with a woman after Sarah, a CIA agent whom Jack had worked with in his Delta days and whom he had frequently referred to as his right one, had married.

For a while, it had certainly looked like that.

And then, by sheer and utter coincidence, Jack's ex-girlfriend's daughter, the girl who'd been almost his own, had re-entered his life, and thus, so had her mother.

Jack had, eventually, realized that he still had feelings for Diane.

(After some nudging from Riley, slightly Parent Trap-style.)

Maybe, just maybe, one could have more than one right one, as contrary as that sounded.

And now, they'd decided to give it another go.

(Mac was optimistic. Very optimistic.)

(After all, this time, Jack wouldn't walk out and leave. He'd regretted that, Mac thought, as much as he'd regretted not telling Sarah how he'd felt about her for years, maybe even more. And he wasn't scared, not anymore, of how much he'd come to mean to Riley, wasn't scared of becoming a father, and Diane and Riley had managed to impress upon him that he was definitely a good enough man for the two of them.)

Jack grinned back, putting his own arm around the blonde's shoulders for a moment, before they both let go. The brunette then pointed at the blonde with his beer bottle.

'Well, now that me and Boze are both coupled up, we gotta find you a woman, brother.' Jack sipped his beer. 'It's real nice to have someone, you know, someone to share your life with, go to sleep next to and wake up to and...'

Mac sighed internally, taking a swig of his own beer.

I know.

Once upon a time, I had that.

Then…well, to put it lightly, it didn't end well.

I'm lonely too, in the way that Jack was.

The way that my friends, my family, as much as I love them, can't help me with.

At least once in my life, I've thought I'd found the right one. Twice more, I've thought that I might have.

Each time, I was wrong.

And each time, it really, really hurt.

I have a high pain tolerance, which I've found out the hard way.

But I have my limits.

There's only so much I can take.

Jack noticed the darkening of Mac's mood, and continued, changing his tone.

'…Not that there's anything wrong with bachelorhood; not having to answer to anyone, being able to do whatever you want, whenever you want, free rein at the dessert table, I mean, you are the reigning Bachelor of the Year, after all…'

Mac shook his head, a little smile on his face, clearly grateful for Jack's attempt to bring some levity into the conversation.

With effort, he matched that attempt, after taking another drink from his beer.

'Unfortunately, I can't make brain-bleach; I'd love to erase that photoshoot from my memory…'

Two days later, Jack Dalton, ex-Delta Force, Jackson Industries' Head of Security and Mac's chief personal bodyguard, sat on the brown leather couch in Mac's living room, worrying about the younger man and staring at the remnants of a cannibalized toaster, a cannibalized DVD player and a cannibalized pogo stick on the coffee table.

It wasn't unusual for Jack to be worrying about Mac.

Not at all.

In fact, he had been, to some extent, for almost all of their acquaintance. Jack had made it his business (his job, literally) to watch the younger man's back, after all.

(Sure, their first few weeks of acquaintance had been…well, contentious, but after saving each other's lives a few times and cultivating some mutual respect, they'd become inseparable. And Jack knew that Mac's back needed watching – he would run towards bombs or fires and the like, not away – and he'd decided that he should be the one to do it. He'd even signed up for another tour of duty so he could keep watching Mac's back.)

It also wasn't unusual for there to be oddities like the toaster, DVD player and pogo stick remains lying around Mac's penthouse.

(Most of his projects – and all of the possibly dangerous ones - were done in his workshop on one of the R&D floors in the building, but some of them resided in Mac's apartment.)

(Those were mostly the 'domestic' ones or the ones that were 'just for fun'.)

(Those were usually the weirdest ones.)

Jack had generally heard that lots of rich people were really eccentric, and could get away with it too, since they were, well, rich.

But he was pretty sure that Mac was far crazier and more eccentric than 'normal' rich people were.

How many billionaires did half of their penthouse reno by themselves?

(He'd at least been convinced to let a licensed electrician and a licensed plumber check over the wiring and the plumbing…though, apparently, both had been very impressed by his skill at wiring and plumbing.)

How many had a house full of random DIY'd stuff?

(There was a remote-controlled flying scarecrow hanging by the door, a gumball machine-based arcade-style game next to the couch, and a pancake-making toaster on the kitchen counter next to the triple-decker waffle iron. Out on the deck sat Mac's modified grill, which could cook a side of pastrami in half an hour, but needed supervision when doing so, as it sometimes caught fire.)

Or owned IKEA furniture?

(Mac loved flat-pack furniture. He actually enjoyed assembling it.)

Ate Honey-Nut Cheerios for breakfast?

(Damn Mac and his ludicrously fast metabolism. If Jack did that, he'd be piling on the pounds in no time. Bozer said it was probably because his BFF used his brain so much – apparently, the brain burned a lot of calories – but Jack was pretty sure that Mac's fondness for running also helped. As did the fact that he was under thirty.)

Or made a hot-tub out of a kiddie pool and a vacuum cleaner, instead of buying a top-of-the-range one and having people install it for him?

(Riley refused to use it, saying that if she wanted to get electrocuted, she'd do it the normal way, but Jack – who'd been a little hesitant too, admittedly – thought that she was really missing out.)

Or had a wardrobe that seriously consisted of mostly identical-except-for-colour chinos and button-down shirts? And a much-beloved, frequently-worn brown leather jacket?

(Jack could respect sticking to your look. He, like Mac, refused Bozer and Riley's frequent and persistent offers of a makeover – he liked his black T-shirts and rock band T-shirts and dark jeans, thank you very much – but he also couldn't stand Mac's fashion sense. He dressed like a grandpa, which was probably because Mac dressed like his grandfather.)

Although, to be fair, Jack thought that Mac would probably be absolutely nuts and really weird even if he wasn't the 18th richest man in the USA.

He'd certainly thought that the young EOD tech was crazy when they'd first met, and then, he hadn't known who Mac really was.

(Mac's grandfather, the founder of Jackson Industries, Harry Jackson, had gone to great lengths to keep his grandson out of the limelight. Great, great lengths. He – and Mac's parents, at least, before Mac's mom died and his dad left – had done everything they could to ensure that Mac had as normal a childhood as possible, including raising him in a perfectly normal but admittedly nice house in suburbia in the Hollywood Hills.)

(That had carried over to Mac, who was intensely private, especially when his grandfather had been alive and he'd simply been the heir to Jackson Industries and the family fortune. Nobody in their military unit had known Mac's true identity. He'd mentioned to Jack a couple of times that his grandfather owned a business which he'd inherit and run one day, but he'd also made it sound like some mom-and-pop operation, not a multi-billion dollar corporation that made just about everything, from household appliances to agricultural machinery to medical equipment, except weapons.)

(Safe to say, when they'd come home for good, and Mac had finally told Jack the truth, he'd been really, really shocked.)

(In fact, at first, he'd thought that Mac was pulling a prank on him.)

(But, once he'd gotten over the shock, Jack had then insisted – quite literally, insisted – on becoming Mac's chief personal bodyguard, since, Jack knew, he'd need one, and there was no-one else he would rather have watching Mac's back.)

He sighed, glancing around at the four other people seated around the living room, drinking beer and eating snacks.

Diane, who was sitting right next to Jack, leaning against his shoulder, though they were refraining from any significant PDA, for Riley's sake.

The young woman herself, who worked in the Cybersecurity division of Jackson Industries, both dealing with the company's cybersecurity and the cybersecurity of anything they made, was sitting on the other end of the couch, next to her mom.

Riley had once been a black-hat hacker, but after a near-miss with a very dangerous and extremely ruthless hacker organization known as The Collective (she'd done a little digging, thankfully, when they'd first approached her, and discovered that they had a tendency to threaten and harm the loved ones of their 'recruits' to get what they wanted) she'd gone more-or-less straight, becoming a freelance IT consultant/tech/white-hat. Still, she kept her toes in the water of the black-hat world, just in case The Collective decided to go after her mom or something like that. When she'd stumbled upon some stuff on industrial espionage at Jackson Industries, she'd contacted Mac's Head of Security (Riley had a sense of morality, after all, and besides, she'd witnessed first-hand a lot of the good works of the Phoenix Foundation, Jackson Industries' philanthropic arm) who'd awkwardly and messily turned out to be Jack. Stuff had then gotten quite complicated and nasty (it turned out that Mac's girlfriend was central to the industrial espionage, which had completely broken Mac's heart, and of course, there was that tension between her and Jack, but everything was good between them now).

Bozer, Riley's boyfriend of about two months, and Mac's BFF who worked in Marketing for JI, was perched on the arm of the couch next to her.

Bozer and Mac had been BFFs since they were eleven and nine respectively. Bozer's parents worked for Jackson Industries, with Bozer's dad in Security (he'd been one of Harry Jackson's bodyguards), and his mom in Legal, plus he had an aunt in Accounting, so Bozer had been one of the few kids at their school who'd known that Mac was the sole heir to JI and really, really rich. Bozer, to his credit, had never breathed a word about that, and had treated Mac perfectly normally. One day, he'd punched Donnie Sandoz, breaking his nose, for beating up Mac, and had been suspended from school for two weeks, during which Mac had gone to the Bozer family's house and done Bozer's homework every single day. They'd been best friends ever since.

And Samantha Cage, former SASR 4th Squadron, former CIA and now a part of JI's Security team, was sitting in the armchair, watching Jack intently in a way that he still found a little disconcerting.

(Cage was an interrogation and behavioural expert. She could hack someone's brain as easily and as quickly as Riley could hack into a computer.)

Jack sighed out-loud again.

These people (plus Matty and Patricia, who were at the business dinner that Mac was stuck attending with him – Jack wasn't there as he'd been heavily encouraged by Mac to take the night off, since the dinner was in LA and there'd be plenty of security there, and besides, Jack headed a very competent security team who could definitely keep him safe for the night) were Mac's friends. Friends who were like family.

They weren't just Mac's employees (well, except for Diane, who wasn't employed by JI) and he and Bozer weren't just Mac's tenants either (they lived in apartments the floor below Mac's, and paid far below market rent – Mac would happily lease some of the other apartments in the Tower, kept for visitors, to his other friends-who-were-family, but Riley, Cage, Matty – JI's CFO – and Thornton – JI's CEO – all insisted on having their own places that weren't in their workplace).

They all worried about him, because there was definitely something to worry about.

Jack sighed again. Diane put a comforting hand on his shoulder.

'It's been almost two months since his shrink started encouraging him to get back into the dating pool, but he hasn't even stuck half a toenail in.' Jack reached up and put his own hand over Diane's on his shoulder, glancing at her. 'And he was genuinely happy for us, like he was with you two…' He gestured to Bozer and Riley. '…but…'

He trailed off, hoping that the others would get it.

Mac had, of course, being Mac, been genuinely happy for them.

But there'd been something sad in his eyes, on his face, in his posture, too.

Something resigned.

As if he was resigned to never finding what Bozer and Riley had found, what Jack and Diane had found again.

As if he'd decided to stop looking, stop trying to form one of those special, meaningful connections.

To be fair to Mac, none of them could really blame him.

Mac had a complicated and painful romantic history. He'd had terrible luck in love.

When he was fourteen, he'd been shot down cold by Darlene Martin, the prettiest girl at his and Bozer's high school and his chem lab partner in Junior year, on whom he'd had a massive crush. She'd only been nice to him so he'd do all the work in chem class, plus all her homework.

Then, in his Senior year, he and Penny Parker had dated for 26 days. Mac's first kiss, first date and first girlfriend was still a friend, but they'd realized quite quickly that their feelings for one another were really platonic.

(Penny, Mac and Bozer were still good friends, though they had less time to catch up with one another now. They still liked to laugh about the fact that Penny was Mac and Bozer's mutual ex-girlfriend.)

Then, he'd spent most of his two years at MIT pining over a fellow student and close friend, Frankie, before suddenly dropping out to join the Army, losing touch with her.

(He and Frankie had gotten back in touch after a chance encounter a couple of years ago in Boston, when Mac had been there for JI business. Jack had encouraged him to see if he and Frankie could be something more than friends now, now that their five-year age gap seemed smaller, since Mac wasn't a teenager anymore, and that they were both single, but Mac had said that A, she was out of his league – which Jack thought was nonsense, but Mac had argued that he simply didn't quite get how special Frankie was – and B, that when he'd chosen the Army instead of staying at MIT, his and Frankie's lives had diverged irrevocably, which he'd said that, in the end, he couldn't regret.)

After Mac had come home from The Sandbox for good, there'd been a nasty incident at the Korman Challenge (a one-off contest run by the military to create an autonomous med-evac vehicle that'd been open to both government agencies and vetted corporations – like JI – alike) with Allie Winthrop, a CIA engineer.

(Mac had really, really liked her, and he'd thought that she'd really liked him, but then she'd taken advantage of the opportunity and snuck a sneak peek at his drone schematics on his laptop…)

And it got worse.

Mac's first real girlfriend, Nikki Carpenter, who'd worked in Cybersecurity at JI and whom Mac had genuinely believed was the right one, had then hurt him even more than Allie had.

(Finding out that your girlfriend of two years, your first real girlfriend, ever, was committing large-scale industrial espionage against you really, really hurt…even if she said that she still loved you.)

After Nikki, Mac had been on a handful of dates with a woman he'd met online named Cindy, and then Jack had been convinced that the secretary of that shady, sleazy German guy (Wexler, he was pretty sure his name was) whom Mac had called out in the middle of an important meeting for sexually harassing her had kinda developed a crush on him (Katarina had invited him to look her up if he ever went back to Germany, after all – which Mac, being Mac, had awkwardly responded to with something along the lines of being terrible at plans, but how about planning to make plans?), and he'd had a handful of first dates and one or two second ones after that, but there'd definitely been no special, meaningful connections, though not for lack of trying.

(They all knew that it'd be hard for Mac to find true love. There was the whole fact that he was the 18th richest man in the USA, which had an unfortunate, sad tendency to attract people who wanted him for the wrong reasons, and then the fact that Mac was, to say the least, a unique individual.)

(There was nothing wrong with that, but the mad-science-ing and crazy DIY projects, unusual interests and slight awkwardness did make it a bit harder to find a perfect match.)

And then…last October, Mac had met Zoe Kiruma, a beautiful, brilliant glaciologist and grad student, after getting into a debate with her online over the age of an Arctic ice core.

Unfortunately, before they could even meet in person, she'd died a hero saving 31 of her students during a school shooting.

She and Mac had only known each other for a couple of weeks, but they all knew that they'd had (or, perhaps a little more accurately, were building) one of those special, meaningful connections.

That if she'd lived, there was a very good chance that she could have been the right one.

(Not long after her death, the Zoe Kiruma Memorial Scholarship had been endowed at her university by an 'anonymous' donor.)

(And it'd taken six months of counselling before Mac's therapist thought he was ready to consider dating again.)

(And besides, they could all see it, even if they didn't have Cage's skills.)

Still, they all held out hope that complicated, distressing romantic history aside, Mac could still find the right one.

He was still only twenty-seven years old. Definitely still young.

And Jack and Diane had had their share of complications, since Jack had thrown her ex-husband around for throwing her around, then walked out of her and Riley's lives immediately and refused to answer all calls and texts.

(After a deeply heartfelt apology from Jack, including the admission that he'd walked out on them because he was scared, because he and Riley and Diane were really becoming a proper family - he'd realized that he was the closest thing to a father Riley had ever had, and he didn't think he was a good enough man for the two of them - and some time getting to know each other again, plus a bit of nudging from Riley and a little encouragement from Mac – Jack had feared screwing it up again, because then he'd lose Riley too - Jack and Diane had fallen in love once more.)

(Not that either of them had ever completely fallen out of love with each other either, everyone else suspected.)

And Riley and Bozer's relationship, was, in Bozer's words, worthy of being made into a movie.

It had, to put it lightly, had its hiccups.

When they'd first met, Bozer had flirted aggressively and endlessly with the woman he'd called his 'future girlfriend' on their first meeting. He wouldn't take no for an answer, until Jack had given him the kick up the ass he'd needed to stop letting his hopes about what they could be get in the way of what they were.

After that, he'd apologized and changed his behaviour (with the occasional backslide which Riley didn't really mind – she knew that Bozer's heart was in the right place, and he really was trying, and old habits died hard, and he was actually cute when he wasn't being overly pushy…), they'd settled comfortably into being friends, and Bozer had moved on and dated Leanna Martin.

Then, that had ended (which, to be fair, was probably what was likely to happen when you went long-distance with someone you'd only known for three weeks, during which you'd had your share of relationship drama – those weren't the best conditions for a relationship to grow), and fast-forward six months, and Bozer and Riley were now two months official.

Cage took a sip of her beer before speaking.

'Mac's heart is guarded towards romance.'

(But, Cage knew, Mac would never close off his heart completely. He simply couldn't, even if he really wanted to.)

(Mac cared, arguably too much, about people in general.)

(It was one of his biggest strengths – if not his biggest; his grandfather had apparently said that his big brain wasn't much good without the big heart to go with it – and also probably his greatest weakness.)

Jack, Bozer, Riley and Diane all nodded in sad agreement, before Bozer plastered a grin on his face, and stood.

'Alright, much as I love my BFF, it's burger time, and nobody's allowed to be sad during burger time!'

Jack gave a snort, but a little grin appeared on his face anyway, while Riley rolled her eyes and shook her head in a fondly exasperated way, a smile appearing on her face, and Diane gave a soft little smile and head-shake. A little smile appeared on Cage's face as well, as she took another sip of beer.

AN: How'd you like that? Did I do a decent job adapting everyone's backstories into this AU? And yes, Mac is the Bachelor of the Year despite being somewhat befuddled as to the why…and yes, of course I 'borrowed' Jackson Industries/Tower/JI from the corresponding Stark Industries things!

The Bozer/Leanna bit is my own interpretation of their relationship – I honestly felt we didn't get much of a basis for it (it might have just been a chemistry thing – for example, Mac and Zoe had less screen-time together, I think, and less actual time, but established a very believable and realistic connection within that), I mean, Bozer was infatuated with her because she was really attractive (and also hyper-competent, confident, sassy and almost didn't even give him the time of day when they first met – seriously, Boze, you so have a type!), and then they had that very brief bonding experience while chasing/being chased by that guy who was spying on the spy school…and then it was sort-of boom! We have feelings for each other! I do see why and how it happened (aforementioned stuff on Bozer's part, bonding experience, plus the fact that Bozer – despite his sometimes-creepy-and-problematic-behaviour – is a genuinely really good guy and Leanna does get to see that and seems to truly value it), but I don't feel it as 'endgame', particularly in canon, where I feel like it's all going to blow up in their faces at some point…