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ask a hopeless romantic

Summary:

Tony glared at his column, trying to come up with better advice than dump his ass. The same person, Loveless in Brooklyn, wrote him every week about, presumably, the same guy. Every week, Tony advised the guy to drop the idiot. Tony had been in enough (failed) relationships to know that it wasn’t worth it to waste your time on someone who didn't want you back. Harsh, but true.

 

If only he could convince himself of that; maybe then he’d stop sending longing glances to Steve Rogers in the art department and move on with his life.

 


or, tony is an anonymous relationship advice columnist and steve really, really needs the help

Notes:

based on this prompt from tumblr

this was a labor of love that i kept forgetting existed, so it took f o r e v e r. i meant for it to be maybe 2k, and it ended at 5.4k, whoops? there are 4 chapters and i'll update every 2 days (probably, counting is not my strong suit), so stay tuned!

enjoy :)

(See the end of the work for more notes.)

Chapter Text

Dear Loveless in Brooklyn,

 

He doesn’t deserve you! It seems like all you’re doing is chasing after this guy- if he hasn’t caught a clue by now, he’s either an idiot or a douchebag. I know it sucks, but you gotta move on, dude. Life’s too short to waste time on people like that. Two years is a long time to pine for a guy who clearly doesn’t have his shit together. Anyone would be lucky to have you- go and find someone worth your time.

 

xoxo The Hopeless Romantic

 

Tony glared at his column, trying to come up with better advice than dump his ass . The same person, Loveless in Brooklyn, wrote him every week about, presumably, the same guy. Every week, Tony advised the guy to drop the idiot. Tony had been in enough (failed) relationships to know that it wasn’t worth it to waste your time on someone who didn't want you back. Harsh, but true.

 

If only he could convince himself of that; maybe then he’d stop sending longing glances to Steve Rogers in the art department and move on with his life.

 

“Stark!” Natasha, his terrifying section editor, smacked the back of his head as she passed. “We needed your column yesterday . Is it done?”

 

“I’m reporting you for abuse,” he told her as he emailed the file, backdating it quickly. “It’s in your inbox. It arrived on time yesterday. Check the timestamp.”

 

“I just watched you send it,” she raised an eyebrow. “Right now.”

 

He spread his hands and shrugged. “Time isn’t real.”

 

“Pepper will make you do the website formatting if you keep submitting things late,” Natasha warned him. 

 

Tony shivered at the thought of their editor in chief. If Natasha was terrifying, Pepper was a literal demon. She was scarily competent, too; he had no doubt that she’d follow through on her threats.

 

“You can’t prove anything,” he said, smiling like a fiend. “Timestamps are on my side.”

 

“One of these days, Stark…” said Natasha, leaving to go harass the other late writers. Tony breathed out a sigh of relief when she left him without any stab wounds, not that he’d tell her that.

 

“Love you, too, Nat!” he called after her. She just flipped him off, leveling a truly ominous smile at Clint, who gulped in fear.

 

Tony pulled up his column again. Ask a Hopeless Romantic was one of their more popular sections, much to his chagrin. He had started the column years ago as a joke, citing his multitude of experience with failed relationships as justification to Pepper. Mainly, he was bored and wanted something new (and he wanted to stop pining over unattainable men, but that was a separate issue).

 

He hadn’t expected it to take off like it did; people really sucked at relationships, apparently, and were more desperate than he thought. He fielded around forty submissions a week, choosing three or four to answer for each edition. Without fail, though, he always answered Loveless in Brooklyn, the theme of pining over a coworker a little too familiar.

 

Steve Rogers was art in human form, in Tony’s absolutely unbiased opinion. The man’s muscles had muscles, for one; he looked like a blond Adonis. Tony could talk for hours about his eyes, if he was drunk. None of that was normally what got him flustered; he could talk circles around anyone, attractive or not, and he had certainly met many gorgeous men and women throughout his life.

 

No, Steve had to be nice , too.

 

Steve went out of his way to say hello to people, to ask about their families and their hobbies and their pets. He never seemed to get exasperated with the general human condition (stupidity, which Tony could attest to) or the chronic lateness of his section. He was always smiling . It drove Tony crazy, that one person could be that good

 

He was either a saint or on some really good weed, Tony hadn't decided yet. Either way, Tony could admit to his massive crush on the man; only, not to Pepper (she’d give him the eyebrows of disappointment), not to Rhodey (he’d embarrass him as revenge), or literally anyone else he knew. 

 

He was fine with pining in silence, really. 

 

It didn’t help that Steve’s particular brand of friendliness extended to Tony, too. Every day, Steve brought Tony a coffee from the break room and stayed for a chat until Pepper or Natasha inevitably yelled at them for slacking off (and by them , he meant himself. It must have been illegal to yell at Steve, or something, because neither woman ever did). 

 

Right on time, Steve with his stupidly sunny smile and unfairly pretty face came up to Tony’s desk, setting his coffee in front of Tony. 

 

“Hey, Tony,” he greeted. “Did you make your deadline?”

 

Tony snatched the cup of coffee and drank it greedily. “Only because Natasha is a slave driver,” he grumbled. “Cruel woman, harassing me because apparently I’m ‘late’ and ‘irresponsible’.” He made finger quotes to show how unimpressed he was with his section editor. 

 

Steve smothered a laugh. “You know,” he teased, flicking Tony’s forehead. “You could always turn in your columns on time.”

 

“Steven, darling, do you even know how much work I have?” Tony challenged. 

 

“I have a feeling you’re about to tell me.”

 

Tony sniffed haughtily. “ Now I’m not, asshole,” he said primly, turning back to his work. “You’re the worst.”

 

“Guess I don’t need to bring you coffee anymore,” teased Steve, making a move to to take the mug. “If I’m the worst and all.”

 

“If you take my coffee, I will take your life .”

 

Steve chuckled fondly. Tony blamed the warm feeling in his chest on drinking the hot coffee too fast, not Steve’s stupidly attractive face. 

 

“Okay, Tony,” he said, holding his hands up in surrender. 

 

Anthony Edward Stark! ” Right on cue, Pepper walked on on her heels of death. 

 

“Oh, shit,” Tony whimpered, trying to remember what he forgot. “Steve, if you’ve ever loved me, you’ll let me hide behind you and tell Pep I’m dead, or something.”

 

Obediently, Steve slid in front of Tony, who had darted under his desk. 

 

“Hello, Miss Potts,” he greeted earnestly, like he wasn’t blocking her view of her victim. “Having a nice morning?”

 

“Wonderful, Steve,” she said warmly. “Now, if you’ll step out of the way? I have a writer to disembowel.”

 

Steve complied easily, probably thinking she was kidding. Tony watched him move aside to reveal an unimpressed Pepper. He could only see her ankles, but he knew she was making her patented look of disapproval. 

 

“Pepper, sweetheart, light of my life and wind beneath my wings,” he tried, standing slowly. Behind her, Steve looked like he had been sucking on a lemon. Maybe he didn’t like seeing Tony disappoint Pepper? “Whatever it was, I didn’t do it?”

 

“That’s exactly my point,” Pepper deadpanned. “I need your feature piece.”

 

“Bruce is on features this week,” Tony said nervously. “Right?”

 

“Wrong.”

 

“Oh, shit,” Tony repeated slowly, fingers twitching at the dangerous tone in her voice. “Have I ever told you you have beautiful eyes?”

 

“Every time you think it will get you out of trouble,” Pepper said sweetly. 

 

“Has it ever worked?”

 

“Not once.”

 

Tony winced. “Steve, a little help here?” he said, glaring at his friend.

 

Steve shook his head. “She could kill me with a single high heel, Tony,” he said. “I’m not getting involved, not even for you.”

 

“Traitor,” hissed Tony.

 

Pepper smiled. “Thank you, Steve,” she said. “Tony, get that piece on my desk by the end of the day, or else .”

 

“Love you, Pep!” Tony called weakly as she left. 

 

“Do you do that with everyone?” Steve asked, face unreadable.

 

“Do what?” Tony said, confused. “Anger them to the point where they not-so-secretly plan my murder? Pretty much, yeah.”

 

Steve made a soft noise of frustration. “That’s not… never mind,” he smiled at Tony. “I should let you get back to work.”

 

“Steve, wait,” Tony called, but the man was already gone, leaving Tony with a lingering sense of unease. 

 

He didn’t have time to dwell, though; Pepper would have his intestines as a scarf if he didn’t finish his piece. But the feeling lingered under his skin, as much as he tried to ignore it.

 

What had he done wrong?