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Everyone knew that Tony Stark was a ladies’ man. Seriously, if you asked anyone to describe him, being a playboy would be in his top five characteristics – along with being a mad genius, fabulously rich, dashingly good-looking, and obsessed with robots. (Well, maybe that might be Tony’s own self-descriptive list, but whatever.) He was an incorrigible flirt, and had probably tried to hit on every single girl at Avengers Academy – including several who were clearly already dating someone else (well clearly in retrospect, he’d still made a fool of himself before he found out).

Anyway, the point was that he had a reputation. What no one seemed to realize (luckily) was that the reason he flirted with so many different women was that they rarely flirted back. He lucked out with a few dates sometimes, but they always got sick of him after one or two outings. He wasn’t saying he was ready to get married or anything like that, but despite popular perception he really would like a steady girlfriend. He’d thought the hot tub and cheese fridge would be a nice draw if his money, tech, or good looks weren’t enough of an attractant, but that hadn't proven the case.

Fortunately he’d just finished designing a new solution to his dating woes!

E.R.O.S. (ie. Encouraging Romantic Opportunities Systematically) was an A.I. specifically written to identify and assess romantic compatibility with potential partners. (He was originally going to name it C.U.P.I.D., but Compatible Understanding Predictive Interpreting Device just didn’t flow off the tongue as well.) The purpose of the program though was to be able to find out who he actually stood a chance with and maybe get a few pointers on how best to woo them. There were so many amazing ladies on campus – sexy Amora, mysterious Natasha, hard-working Pepper – surely one of them would be his perfect match. With any luck, by the end of next week he will have found the girl of his dreams and swept her off her feet!


Tony decided to start with Natasha figuring he’d known her longer than most of the others (she was one of the first people at the Academy besides him and Jan), and she had even gone out on a date with him before. Maybe his A.I. could figure out what had gone wrong with that previous date so he could do better this time.

With some pointers from E.R.O.S., Tony managed to convince Natasha to stop by Stark Tower. When she arrived, however, she sent him on a wild goose chase for a different kind of cheese (which was an insult to the quality of his cheese fridge!) while she hacked into his computers. After that horrible failure of a date, E.R.O.S.’s compatibility score of 28% really wasn’t a surprise.


Deciding to swap to one of the newer students, Tony tried spending some time with Santana. It was fun being the one chased instead of the one chasing, but she kept trying to eat his soul instead of his cheese. So maybe not.


Tony had always had a bit of a crush on Pepper. She could be a bit of a killjoy sometimes, but she was so ruthlessly efficient and usually took his flirting with good humor. She’d been very pleased with the Rescue armor he’d made her, and E.R.O.S. said they had a 56% compatibility. This was the highest percentage he’d seen yet – over halfway! Plus, she’d known him forever too, and that had to count for something right?

According to E.R.O.S., Pepper really wouldn’t be impressed by big, over-the-top displays, and would instead be more likely to respond to maturity and sincerity. So Tony put on his nice “I mean business” suit and brought her a single rose (E.R.O.S. said two dozen counted as over-the-top). It took him twenty minutes to convince her that he was serious, but in the end Pepper agreed to a date.

E.R.O.S. was so worth the sixty hours of coding he’d spent to create the program!

The first date was supposed to involve drinks at Club A, but they’d been interrupted by a call from Fury with a supposed emergency. (Tony didn’t know what kind of administrative problem would warrant being called an “emergency” given that none of the other Avengers were being called to fight new aliens or anything. He’d wanted to hack into Fury’s account to see what was going on, but E.R.O.S. said Pepper would be mad if she found out. Ugh, dating was hard work.)

The next few dates were actually successful – until Tony realized he mostly ended up doing paperwork and agreeing to safety regulations and other thoroughly un-fun things. Was having a girlfriend really worth it, if he found their dates boring?

Tony decided that maybe he needed to stick with higher compatibility percentages. Clearly >50% wasn’t a high enough bar. (Pepper was very nice though – and possibly relieved – when he said the dating wasn’t working, so at least he hadn’t lost that friendship.)


Enchantress frequently liked to use his hot tub and put him under love spells which was a plus, but according to E.R.O.S. they had a strikingly low 8% in common – which mostly consisted of the fact that they both thought she was beautiful.


Peggy Carter was a lost cause as far as Tony was concerned and he avoided looking at his percentage score with her, but that was more because they both agreed that dating someone who was your dad’s colleague was just too weird. (He’d leave that intergenerational awkwardness to Cap and Agent 13.)


He also avoided Madame Hydra. Tony was all for a bit of danger in his love-life (see his earlier attempts with Black Widow and Satana), but she freaked him out a little too much.


Tony whooped when he saw that he’d scored a nice 71% with Hellcat. She was a fellow cheese-lover who enjoyed spending time at his tower. Plus Patsy had a great sense of humor. On E.R.O.S.’s advice, he invited her over to the tower for a cheese party, keeping it nice and casual to work up to asking her if she’d be willing to turn their hangouts into real dates. Only, she didn’t seem to be picking up on his casual flirting. E.R.O.S. kept saying that coming on too fast could scare potential dates away, but maybe the program was wrong because clearly Tony needed to step up his game to make his interest more obvious.

E.R.O.S. had been right. Or maybe not, but when Tony had shown up at Hellcat’s door with a gigantic bouquet of cheese-flowers she’d turned him down. Oh she’d loved the cheese-flowers, but apparently after having her last two (ex-)boyfriends turn evil she wasn’t really interested in dating for a while. Unfortunately, Tony wasn’t really sure of a way to have E.R.O.S. incorporate past dating history into the compatibility scores.

Even upset as he was to have his date shot down, Tony still agreed to continue their cheese party hangouts because it never hurt to have more cheese-loving friends. Nevertheless, he was back to the dating pool.


He had no luck with Mary Jane, Black Cat, or Spider-Gwen because they were all apparently more interested in Spider-Man (which was so not fair that Parker had three gorgeous women chasing after him!).


Agent 13? [Compatibility 19%]

Not surprising considering she was so obviously hung up on Cap and was a “serious” SHIELD agent – and by “serious” he meant not a fan of Tony’s disregard of the rules. (Although who at Avengers Academy really followed the rules? Well, except Cap… and Pepper… and Maria Hill… and Coulson… and, ok, nevermind, but that didn’t mean he was the only troublemaker around.)


Gamora was super-hot and Tony was an equal-opportunity guy when it came to alien skin colors. He even scored 51% with her – before discovering to his horror that she was lactose-intolerant and didn’t like cheese (something about her alien biology), which no. Just, no.


Many, many dates (or attempted dates) later, Tony was starting to feel discouraged. He’d nearly run through all the women currently at the Academy. Sure, there’d probably be new recruits eventually, (he’d heard rumors of an all-female team that might be coming), but he was starting to wonder if maybe the problem was him after all.

Reluctantly, he glanced over the latest data from E.R.O.S.

[Compatibility 89%] 

Wait, what? That sad attempt at a date had been a disaster.

[Compatibility 10%] 

Uhh-huh, that was weird.

Looking more closely, Tony found that there were actually two sets of data. Yes, his failed attempt at chatting up Maria Hill had been abysmal and had ranked only 10%, but he had forgotten that on his way back to Stark Tower he’d run into Jan who had solicited his help for planning a Holiday party. (They always threw the best parties together!)

Stunned, Tony sat back in his chair – only to discover he hadn’t been perched on it very straight and instead fell back on his butt still staring up at the screen. Jan. The Wasp. Janet Van Dyne. She was an 89% match. His best bestie was also his best match.

Suddenly Tony felt like an idiot. He and Jan had tons in common. They were both the best partiers and party-throwers on campus. She loved technology almost as much as he did, even if she focused more on communications-based tech outside of her suit. Even better, she liked him! Well, maybe she didn’t like him like him, but he could find out. She was cute, smart, fiery, outgoing, and she’d always stuck by him (well mostly, and they’d already talked out that Civil War thing). She was perfect! How had he missed this ultra-important fact? He was an idiot. No wait, he designed the E.R.O.S. program that helped him figure all this out, so therefore he was a genius! Hah!

Okay, next question – did Jan maybe like like him. He had thought maybe she had a thing with Ant-Man, but a quick check on Facebook showed her status was still single, so clearly it wasn’t a real relationship.

Scrambling back onto his chair, Tony started writing out code for the biggest holographic bouquet of flowers he could manage. Maybe he could flood her twitter page? Ooh, ooh, maybe he could create a fleet of tiny robots shaped like wasps to spell out “Will you go out with me?” and then fly in formations like hearts and stuff. Quickly, Tony swiped E.R.O.S. away to the background as he got to work.


– One week later –

Jan squealed and leaned over to give him a quick kiss as they sat in his workshop together working on a new social media platform just for the Avengers Academy. (It was going to be called the AVACADO or AVengers ACAdemy DOmain. Jan was awesome with cool names too!) On the table behind them was a half-eaten platter of cheese they were both snacking on. Later, Jan wanted to go out flying together, then maybe go to the blasting range or just relax in his hot tub. He had the best girlfriend ever!

He didn’t even need E.R.O.S. giving him advice on wooing – the happy squeal and kiss he’d gotten after tracking down another unicorn had been the best feeling ever. (Plus, Tony Stallion appreciated the company.) Now he was just trying to locate a giant bee that breathed fire…

Also, did he mention that he was a genius? E.R.O.S. was definitely the best idea ever, never mind what Steve said – he was just sore because the A.I. said he’d be better suited to Black Widow than Agent 13 or Peggy Carter. Tony wasn’t about to get between a super-spy and a super-soldier to get them to hook up, but he did give E.R.O.S. to Jan who had been more than happy to match-make as many people as possible. (Coulson and Pepper seemed disturbingly chipper about doing paperwork together, but Jan insisted they were cute.) Tony just hoped that if she ever found a match for Fury that he wouldn’t have to hear about it.