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when in Rome

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Sometimes, sometimes, Winn thinks Kara is secretly evil. Like, there’s gotta be a tiny, dark voice in her head that sometimes takes over and makes her do things like this.


Things that are going to get Winn killed. Or worse, in jail. For life.


Okay, no, but honestly, this time he should’ve seen it coming, and to be fair, he did notice that weird little glint in her eyes that she only ever gets when she’s plotting. Once upon a time, that meant maybe pranking her sister or having two-days movie marathons. But, oh no, not this time.


This time it meant sending Winn to a fancy-pants restaurant on a blind date.


See, this is one of those things that are definitely going to end up with murder. It might be his, it might not– the jury’s still out for that one.


Because Kara had absolutely refused to give him any information on who he would be meeting. It’s a blind date, Winn, she had said. You’re not supposed to know, she had said. And she had giggled.


And because Winn is clearly a pushover and, truth be told, his apartment just doesn’t quite feel like home, not since he came back to this century– it’s too big, too empty, too quiet– and the idea of going to sleep with a warm body beside him did have some appeal, Winn said yes.


Thus, bringing him here, to this moment, the very first chapter of his future memoir that he’ll write from prison while serving his life penalty for manslaughter. Alienslaughter. “No, no, no. Absolutely not,” Winn says, still standing by his supposed table and with his supposed date sitting looking just as shell-shocked. “You’ve got to be kidding me. No. I’m going to kill Kara.”


“I don’t understand,” says Brainy, because Brainy is his blind date. Because Kara is an evil, evil person. “I was told to come here for a date. What are you doing here?”


“Is something the matter?” says the waiter.


“Just one second,” says Winn to the waiter, before whirling back on his, and Winn has to give Kara this– it was a surprise, alright– date. “ I’m your date, dumbass. Kara told me the same thing. We were set up!”


“Alex might think I should find a companion in this time,” Brainy scoffs, and it’s a true feat how much arrogance he can fit into it, “but she would never think you would be a suitable choice.”


Winn had really been about to walk away, seriously, he had. He was going to be the bigger man and walk away without a scene, but, you know what? “Excuse me?” He did not wear a blazer for this bullshit, Jesus Christ. “For your information, I am a catch, okay? You wouldn’t be so lucky to land a date with me, okay?”


Brainy raises his eyebrows, and when the waiter opens his mouth again, he waves him off distractedly. “One more second, please,” he looks Winn up and down with a judgy face, and Winn resists the urge to cover himself. He’s not a piece of meat, okay? Jesus. “I suppose I would not know the standards of this century enough to cast judgment.”


“Oh my god,” Winn throws his hands up in frustration, “can you chill on the condescension for like five minutes?”


“I was merely stating a fact–”




“Is it necessary to be so crass–”


“Don’t bullshit me then, and you won’t have to hear me call bullshit.”


“Gentlemen!” The waiter screeches, and both Winn and Brainy and probably half of the restaurant turn to look. The guy clears his throat, valiantly ignoring the attention, “I’ll have to ask that you keep it down, or I will be forced to ask you to leave.”


It’s a cross in the road. Winn could still walk away, call a cab, go to Kara’s apartment, and demand to know what terrible thing he did to deserve such punishment. He looks at Brainy, finds him already looking back, seemingly in the same line of thought.


On the other hand, this is a nice place. And so hard to get reservations. It would be a shame to waste it– actually, that would be letting Kara and Alex win. And oh no, that won’t do. They think they can mess with them and that’s it?


Winn sits down.


“What are you doing?” Brainy asks, and man, the confusion on his voice is sweet, sweet revenge.


“I,” he drawls, picking up the menu, “am ordering my dinner.”




“Dude, this is a nice restaurant. I’ve been trying to get a reservation here for ages, I don’t know what kind of magic Kara and Alex did to get one, but I’m not wasting that just because you guys are a bunch of assholes.”


Brainy looks baffled. Then offended, “why am I included on that? Must I remind you, I was tricked, just like you.”


“Yeah, but it’s the principle of the thing, you know?” Winn shrugs, turning back to their waiter. “Sorry about that, I would like this one here, see? And the wine, too, yes. Thank you.”


The waiter– Matthew, according to his nametag– sighs. “Very well,” then, turning to Brainy, “will you be ordering as well, sir?”


Winn raises his eyebrows and grins in challenge. A matching sigh from Brainy. “Yes, I suppose I will.” He rattles off his order in perfect French, of course, and waits until their waiter has left for the kitchen to narrow his eyes at Winn, “this is not going to end well.”


It’s Winn’s turn to scoff. “Please, have a little faith, will you? As long as we don’t kill each other, it’ll be fine. I’m not turning away free food because of you.”


“Free food?”


“Yeah, you think I’m paying after this little stunt they pulled? Oh, no, sir. They are going to reimburse me even if it’s the last thing I do.” A new waiter brings them the wine, politely ignoring their weird ass conversation. She fills Brainy’s glass first, then Winn’s, and yeah, this is not going to work. This is definitely not a two-glasses of wine night. “Hey, you know what, why don’t you just leave the bottle here? Yeah, just, leave the bottle. We’ll take care of it ourselves, don’t worry. Thanks.”


She leaves the bottle.


Winn knocks back a glass, pours himself another.


Brainy sighs.




“Yes! That’s what I’m saying, man,” Winn leans back on his chair, hands gesturing wildly, “they can’t just mess with us like this with no consequences!”


“Or they will not stop the messing,” Brainy agrees, nodding fervently, “the messing will go on,” he pauses, leaning in, and Winn is at the edge of his seat for this, “forever.”


He can’t help snorting on his glass. They are on their second bottle of wine, waiting for dessert, and Winn can’t believe he’s saying this, but the night wasn’t so terrible. He even wanted to gut himself with a blunt knife only twice. That’s got to be a new record somewhere. “Man, I have to say,” laughter bubbles up again, “you are a lot less dickish when you’re drunk.”


“I have to agree. You are a lot more tolerable as well,” he says, still nodding, “I wonder if this was their plan all along?”


“No, no. Kara definitely expected me to storm dramatically out of the building, cursing your name at the wind,” Winn can even imagine it, picture it on his head. “Alex too, probably. Maybe some water throwing, endless arguing, that sort of thing.”


“They will be very surprised, then, when we tell them tomorrow that no water was thrown.” He amends, “there was some arguing, though.”


“Dude!” Winn knows he must be looking like a crazy person right now, but whatever, that doesn’t matter, because he just had the best idea ever. “I know what we need to do. They think they can just go around and mess with us, right? Well, we can’t let that slide– that would set a precedent. You said it yourself, it would go on forever. Oh no, we need to fight back. So, you know what that means, right?”


“Yes…” Brainy draws out the word, clearly in deep thought. “We throw eggs at their houses!”


“No– what? No! Where did you even– what?”


“Kara has told me I should watch more movies. I believe we are currently watching all of the 90s genre.”


“No, that’s crap. Don’t take life lessons from movies, man. Especially 90s movies,” Winn shakes his head, trying to clear out his thoughts from Breakfast Club references. “Anyway. We should mess with them.”


“Oh,” Brainy looks as if Winn had just told him the secrets of Life, the Universe, and Everything Ese. No, wait, that’s 42. But still, it’s the same sentiment. “And how do you propose we do that?”


“I’m glad you asked that my friend, sort of,” he grins, “we pretend this little blind date thing worked. We tell them we’re dating. I know, genius, isn’t it?”


Brainy stares at him, cheeks still flushed from the wine but eyes surprisingly clear despite the alcohol. It would be cute if it weren’t Brainy. “You are drunker than I thought.”


Winn scoffs. “No, I’m tipsy. But that’s beside the point,” he leans in, drinking the last of his wine, “just think of their faces tomorrow morning. They think we are killing each other right now as we speak. Imagine their surprise if we waltz in tomorrow dating.”


“They would be very surprised,” Brainy concedes, “and it would be funny. I could hack in the security system later, print out a few copies of their bewildered faces.”


“See, now you’re getting it!” Winn crows, still grinning so wide his cheeks are beginning to ache, “what do you say? Boyfriends?”


“I believe,” Brainy smiles, a true mischievous smile that Winn’s never seen on his face before, “you’ve got yourself a deal, boyfriend.”


Winn laughs, raising his glass for a toast, and Brainy clinks his own glass against Winn’s– the official start of a plan that could only go uphill from here.