A/N: I took some liberties with Pepper and Will's backstory.

When Tony and Pepper stepped out for a formal dinner at her favorite fancy restaurant one night—it had a dance floor, that's how fancy it was—he didn't expect to be jealous. He also didn't expect to run into Will Schuester.

They were walking in the establishment and were about to head over to the hostess for their reservation when a name rung out amidst the dinnertime chatter.

"Holly Holliday!"

Normally, Tony would have blocked out that sort of thing but who the hell had parents that named them Holly Holliday?

A man, vaguely familiar, strolled over to where he and Pepper stood and was beaming at their direction. Tony was about to turn around to see if Holly Holliday was behind him when Pepper broke into a grin and responded with, "Will Schuester, it's good to see you!"

Pepper? Tony looked on, stunned, as the man, this Will Schuester—a good looking man with sandy hair and a cleft chin—pressed his hands on both sides of "Holly Holliday's" cheeks. Okay, what the hell was happening? A random stranger had his hands on his girlfriend. Alert. Alert.

"You look amazing!"

Pepper smiled demurely and enveloped the man in a hug. "You too! Are you with Emma?"

Will shook his head, pulling away. "I'm flying solo tonight."

Pepper turned to Tony, introducing him. "Will, this is Tony Stark. Tony, Will Schuester, an old friend of mine."

Tony quickly recovered, hiding his astonishment and smiled at Will. He shook his hand saying, "You look very familiar. Why is that?"

"You saw him in the video," Pepper answered for Will.

"He saw it?" Will asked, breaking into a smile.

"What video?" Tony asked.

"The one where I was singing with high school students."

Tony racked his brain for a memory. One came up."You mean your sex ta—"

"—the one where I was wearing lots of leather, yes." Pepper cut in before he could finish saying the word.

A few weeks ago, a video from a "Will" was sent over to the house. It was addressed to Pepper but Tony watched it out of curiosity; he discovered his girlfriend wearing leather (which she never usually does) and seductively dancing to Do You Want To Touch Me with high school students. Tony called it Pepper's sex tape. She, obviously, disagreed.

"Oh, that video. Now I remember." Then Tony wagged a finger at Will. He remembered this guy alright. This was the guy Pepper kept flashing her boobs at while she was dancing. She may have had a tank top on but clothed boobs were still boobs. "You're Will, the Glee Club teacher." Tony remembered feeling jealous as he watched the guy in the video. Seeing him in person right now did nothing for the awakened green eyed monster in him. He kept his cool, of course, because he was Tony Stark and he didn't do blatantly, conspicuously jealous. "I kept asking about you but she wouldn't tell me anything more. Thanks for sending that by the way, made my day. I didn't know she could sing and dance like that. Really spiced things up in the bedroom."

Pepper elbowed him while Will whistled and gave Pepper a look that Tony thought was a little bit too appreciative...or maybe that was just Tony because Pepper was indifferent.

Tony shifted, annoyed.

"If you only knew," Will said. "Holly Holliday could party."

Tony forced himself to laugh. He placed his hand around Pepper's waist. If Will Schublig here got away with touching her face right in front of him, Tony wasn't gonna back down. He asked her, "Why are you Holly?"

Pepper and Will locked eyes and they both giggled at what was surely an inside joke. And that's when Tony began to feel a little left out. And of course there was also that bubbling pot of jealousy because Pepper never giggled. She giggled when it was just the two of them, usually because Tony said or did something funny, but she never giggled in public! Especially not with other people!

Tony's mouth twitched. He wasn't the possessive-asshole-when-jealous type. He was more of an impulsive-idiot-and-he-hoped-kind-of-endearing-when-jealous type. So, it wasn't really a surprise when he blurted out, "Hey, d'you have a table yet?"

Will shook his head. "I'm on the waiting list."

"Why don't you join us?" Tony asked.

Pepper stared at Tony suspiciously. Since when did he invite people he barely knew to dinner?

Reading her mind, Tony assured her and Will, who already looked like he was about to decline, that it was totally fine. "This way you can tell me all about Holly Holliday. I know there's a great story in there."

"Wow," Will said, "Well, I'll take you up on that offer because I'm starving."

"Perfect!" said Tony, pulling his hand away from Pepper and offering her his arm. "Let's get our table."

Pepper sent him a knowing look. "I know what you're up to, Tony," she said to him quietly so Will wouldn't hear.

"Who says I'm up to anything? I'm just being nice to an old friend of yours." He made a show of kissing her cheek but whispered, "Don't think I haven't forgotten you flashing your boobs at him in that sex tape."

Pepper hit him on the chest. "For the last time, it was part of the choreography! And stop calling it that. People might get the wrong idea."

"Alright. But I'm not going easy on him."

They had originally reserved a table for two but being Tony Stark meant he could change it to a table for three on such short notice. Tony pulled out a seat for Pepper, beating their waiter to it. After they each had ordered their food and got served their wines, Tony turned to Will. "So, Holly Holliday. How did that happen?"

Will laughed and consulted Pepper, "Do I tell him or—"

"Go ahead. You christened me that anyway."

Tony's eyebrows shot up in interest. So, he wasn't the only one to bestow a nickname on Virginia Potts.

"Okay, so I met Holly in college and she wasn't Holly then. She was Virginia. We were both in the college glee club and every Christmas, we would go around and sing carols. By the way, this is the girl you want with you when it's cold and freezing! The things she could do with her hands!" Tony's blinked. Did he hear that right?

"Anyway, there was this one time, she fudged up her solo of Deck the Halls and ended up singing a very croaky 'Holly.' And that never happens! She never croaks! But she did and I started calling her Holly Holliday ever since, as a reminder that she's only human even if her voice is that of a goddess." Will gazed adoringly at Pepper and Tony couldn't help but think that this wasn't how old friends acted; Tony never gazed at Rhodey. Will was acting more like an ex-boyfriend that you were on good terms with.

Pepper buried her face in her hands at the memory. "I hated that name!"

"I love that name!" said Will, "It's like your brand cause, you know, you're always so loosey goosey and fun."

Tony had to do a double take. Loosey goosey? Pepper? With this guy? Now, that was just plain unfair.

"Back up a minute," the billionaire said, "Loosey goosey? You're kidding."

Will shook his head. "The first time I invited Holly to teach the Glee Club with me, my students buttered up the floor so she'd trip."

"But I didn't," Pepper said proudly.

"But she didn't."

Pepper shrugged, pointing her thumb at Tony, "I work with him for a living. If they think buttered floor was gonna intimidate me, they've got another thing coming."

"She also sang CeeLo Green's Forget You and after that brought everybody to Taco Bell. The kids were so impressed at the fact that she let them skip class, they fell a little bit in love with her. I did too! I mean, who isn't at this point, right?"

"Wow," Tony said, capturing Pepper's hand on the top of the table, playing with it a little as he gazed at Pepper this time (he hoped Will was watching). "You never even let me skip meetings! Why is it that you're loosey goosey with kids but you're so no-nonsense with me all the time?"

"Because they're children while you're an adult."

"Who has an inner child inside him too and is feeling a little unloved," Tony added with a grin. "So, Will, tell me about that video with Holly. Are there any more I should know about?"

Pepper shook her head good naturedly while Will nodded. "Oh, there are tons. We always record our performances so we know which areas can be improved."

"And do you choreograph those performances?"

"Sometimes. But if you're referring to the one I sent, that was all Holly."

"Really." Tony sent Pepper a smug smile. She giggled and Tony couldn't help but preen at the sound. He caused that. Not Will.

"He thinks it was a little racy for a high school number," Pepper explained.

"Well, it was a little too much but it still followed the theme of Sexy. So, overall, it was a fantastic number."

"Ooh!" Pepper extended her hands across the table at Will and Tony pouted at the loss of contact. "Do you remember when we did that Umbrella/Singing in the Rain mashup?"

Will touched a hand to his chest in a heartfelt gesture. "Sharing an umbrella with a gorgeous woman was the highlight of my career."

Tony was glaring openly now because Will was shamelessly flirting with his girlfriend in front of him! Not that Tony disagreed with his compliment.

Pepper didn't seem to mind and instead said, "That choreography was insane! I still have dreams about it."

"Well, I couldn't just let you finish your visit with a lame number." They laughed and Tony joined them even though he couldn't relate to anything they were saying much to his growing irritation. There was nothing Tony hated more than being ignored.

"You still dance, of course?" Pepper asked, sipping her wine.

"Of course! Working out by dancing is more fun than going to the gym."

Tony resisted the urge to roll his eyes to the back of his skull because he could dance too. Anybody could dance and sweat it out. But can anybody save the world?

"Saving the world also burns a lot of calories," he couldn't help but say.

Pepper touched his arm which Tony knew was supposed to make him back down but he was done being polite.

"Well, saving-the-world workout wins for sure." Will admitted, shaking his head. "My kids will never believe that I had dinner with a celebrity much less Iron Man."

"Hey, don't sell yourself short," said Pepper. "You're an amazing mentor."

Tony drummed his fingers on the table, trying hard not to glare at Will Schuester. The man didn't have anything Tony should be jealous over; Will was an underpaid teacher while Tony was a rock star—well, a superhero but that was almost like being a rock star. But Tony couldn't help it; Will and Pepper clearly had a connection with dance and music and Tony wanted in on that too. And to top if all off, Pepper was loosey goosey around William and not with Tony. That one hurt the most.

Suddenly, Will perked up and pointed a finger to the air, listening. "They're playing Kiss!" He held out his hand to Pepper, "Care to dance for old time's sake?"

Tony frowned. Dance and have a repeat of that sexy number—rub it in Tony's face? No thanks.

Tony steeled himself with what he was going to do. He knew this would make the news, but despite red and gold being his favorite colors, it seems he was going with green tonight.

Tony took Will's outstretched hand. "I thought you'd never ask."

Will blinked, no doubt trying to process the fact that Tony had just hijacked his invitation to dance. He recovered after a second and said, "I'm always down for something new."

Pepper started to shake her head. She grabbed Tony's hand to stop him. "Tony—Will, you don't have to—"

"Are you kidding me? Dancing with Iron Man is on my bucket list."

"Really?"

"It is now." Will turned to Tony, "You know how to tango?" The song was Prince's Kiss and Tony had never seen it done as a Tango before but he'll be damned if he let Will one-up him.

Tony sauntered to Will's side. "I had dance lessons when I was a kid. Hated them but I was good."

Behind them, Pepper buried her face in her hands with an "Oh, God." She should have known Tony would do something like this.

Tony and Will walked hand in hand to the dance floor, ignoring the looks they got.

"Very well, then. You lead. Show me what you got, Dancing Man." Will placed his hand behind Tony's shoulder while Tony's hand was on Will's back. Their free hands were clasped together, extended to the side.

"It's Iron Man," Tony said, pulling Will against him a little roughly than necessary.

And then it was a dance off... Or for Tony it was because Will was honestly having one hell of a good time, working on some foot play and letting Tony dip him low to the floor.

While they danced, Tony finally asked, "Okay, I gotta ask, because it's killing me not knowing. Were you and Pepper ever together?"

"Yes," Will replied and his honesty surprised Tony. "But it was short-lived. She broke up with me."

"Hmm. Maybe it's because you compliment her too much."

Will laughed. "It was because I was in love with someone else."

Tony almost tripped as they stepped to the side. "What? Have you seen that woman? She's perfect and funny and smart and makes those adorable rare giggles. How could you not be in love with that?" Will raised an eyebrow at him and Tony said, "You know what I mean."

"Well, you're right. She is one of a kind, a walking ball of joy. But my wife is just as amazing and she and I fit perfectly together, much like how you and Holly do, no doubt."

Tony dipped Will again. "Your wife?"

"Yeah, I'm married." Will's eyes widened in realization. "Oh, you didn't think I was—"

Tony pulled Will up and stopped dancing, "Yeah. 'Cause you were being all touchy, cupping her face, and flirting with her and being reminiscy—"

"That's only because she's Holly! After the breakup, she became like a sister to me and flirting with her is like a running gag between us. I don't want to get back together with her! I love my wife! Holly was the one who even told me to ask Emma out!"

"Okay, I admit I may have misjudged you a little bit but also, we're dancing a tango! We're way beyond awkward now." Will laughed.

"It's fine. I get it." They took one step away from each other. "If it's any consolation, the last time someone hit on Holly, I got really mad at her."

"Oh, I bet she did not like that at all."

"Yeah. We broke up a day later." Will clasped Tony's arm and looked him in the eye. "You're handling this way better than I did."

Tony smiled gratefully and nodded his head back to their table where the food and Pepper were waiting. "Want to stop gazing at each other and go back to our woman?"

Will chuckled. "Don't let her hear you say that."

"Yep. Already regretting it."

The rest of the evening turned out a little differently and if Tony hadn't expected to be jealous on this date, he definitely didn't expect to like Will Schuester himself afterwards.

A/N: Thanks for reading!