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Toronto, 2004
“You haven’t been social enough since starting high school,” Gilfoyle’s mom said as she pulled up in front of Brent’s house. “You used to go over to friends’ houses all the time. This will be good for you. Why are you acting grumpy? Do you not like this Brent kid?”
“He’s fine. I don’t really know him,” Gilfoyle said. “I just wish I’d been asked instead of you and his mom just deciding I’m going to spend the night at his house.”
Gilfoyle’s mom rolled her eyes and said, “Bertram. It’ll be fun. Stop being stubborn.”
Gilfoyle grabbed his backpack and stepped out of the car.
“Bertram,” his mom said in a stern voice. “I love you.” She crossed her arms and looked at him expectantly the way she always did when she told him that.
“I love you too, mommy,” he said in a quick monotone.
Gilfoyle sat down on Brent’s bed. He looked around the immaculate room. “Uh, thanks for inviting me over,” he said politely.
“I didn’t, really,” Brent said. He frowned and said, “That sounded mean. It’s just… my mom decided I should have more friends. So, she asked me to pick someone from Sunday school and invite them over.”
“Why’d you pick me?” Gilfoyle asked curiously.
“You seem cool,” Brent told him with a little smile.
Gilfoyle gave him a slight smile back. “So, there’s no one at your school you wanted to have a sleepover with?”
“I’m homeschooled,” Brent said.
“Oh, wow,” Gilfoyle said. “Is that… okay? I don’t know if I could spend all day with my mom.”
Brent laughed and said, “It’s not as bad as it sounds. Do you want to play a board game?”
“Sure,” Gilfoyle said.
“Do you think all the stuff we learn in Sunday school is real?” Brent asked. It was close to 3 a.m. and the conversation was starting to get deep.
Gilfoyle sat up so that he could look at Brent, who was in his bed while Gilfoyle was on an air mattress on the floor.
“Not all of it,” he said. “I figured out my mom is wrong about the Earth being 6,000 years old a long time ago.”
“This is going to sound really bad, but sometimes I hope none of it is real,” Brent said.
“None of it?” Gilfoyle asked with surprise.
“Do you ever, um… just panic thinking about hell and everything?” Brent asked him.
“All the time,” Gilfoyle said softly. “But, my mom always reminds me that Jesus died for our sins…”
“Mine too,” Brent said. “It never makes me feel better.”
“Me neither,” Gilfoyle admitted. He curled up with his chin resting on his knees and asked, “What, um… what kind of stuff do you feel so bad about you worry about going to hell?”
Brent sat there biting his thumb nail for a minute before he said, “You first.”
Gilfoyle looked down and played with the drawstring of his pajama pants. “I think about violence a lot,” he said.
“Really? What kind of stuff?” Brent asked.
“I don’t know. I’ll be sitting somewhere and imagine stabbing someone or something. I’ve never told anyone this…”
“It’s okay!” Brent said immediately. “I’m not judging you.”
“I’d never act on it and I can’t help it,” Gilfoyle told him. “I don’t know why it keeps happening to me. I guess I’m a little insane, but I worry sometimes that it’s more than that. That it’s, you know, Satan.”
“That’s so intense,” Brent said softly.
“Yeah, well, I guess whatever you feel bad about doesn’t seem so bad now,” Gilfoyle said, trying to keep his voice light and hoping that Brent would tell on him.
“I don’t think about hurting anyone, but it’s still a little bad,” Brent said.
“Tell me,” Gilfoyle said.
After a long pause, Brent asked, “You know how sometimes guys’ll wear baggy pants without a belt and their pants sag down really far?”
“Yeah…” Gilfoyle furrowed his eyebrows. When Brent didn’t say anything else, Gilfoyle slowly put it together. “Oh,” he said. “Well, you know, a lot of people don’t think that’s bad at all. That church near the U of T campus has a pastor who’s married to a man.”
“Yeah,” Brent said. “I guess that’s true.”
Gilfoyle rested his hands on Brent’s bed frame and said, “I think you’re right about what you said before. None of it is real.” He smiled a little saying it out loud.
“Yeah, probably not,” Brent said, smiling slightly back at him.
Gilfoyle leaned forward. After only slight hesitation, he asked, “Do you think we should kiss?”
“Yeah,” Brent told him.
The kiss itself was gross and slobbery and it was very apparent neither of them knew what they were doing. But, the feeling of doing something he wasn’t supposed to was deeply satisfying.
Toronto, 2006
Gilfoyle didn’t normally like going out to eat with his parents, but tonight he was too excited to complain. He watched his mom cut up his steak, without complaining about how he was too old for that kind of doting behavior.
“So, I already know what car I want,” he said. “I found a used truck so you won’t even have to spend that much.”
“We wanted to talk to you about that…” Gilfoyle’s mom said.
He frowned. He realized he should’ve immediately known that they’d only suggested going out to dinner so he wouldn’t make a scene. “You guys have been telling me you’ll get me my own car after I pass my driver’s test since I was twelve and I did it. What could possibly make you change your mind?”
“Your behavior,” his mom said. “Staying out all night. Going who knows where.”
“I’m not doing anything that bad!” Gilfoyle said. “You can’t expect me to just stay home every night, studying and praying or whatever.”
“You’ve come home drunk four times now,” Gilfoyle’s mom said.
Gilfoyle felt some satisfaction at the fact that he’d actually come home drunk much more than that and his mom had only noticed four times. “I’ll stop,” he lied.
“You know how much scarier the idea of you drinking would be if you had a car?” his mom asked.
“What if I behave well for a month or something? Then can I have a car?” Gilfoyle asked.
His mom shook her head and said, “You’ve lost your chance. You’re reckless and you’re scaring us.”
“You’re not scared or worried about me. You’re just mad,” Gilfoyle said. “But, you can’t stop me from doing whatever I want to do. I don’t care what stuff you refuse to buy me.”
His mom shook her head and said, “Eat your dinner, Bertram.” She sighed and said, “You used to be so good. I don’t know what happened.”
“I don’t know. I guess it’s just a reaction to you being an enormous cunt,” Gilfoyle said.
His mom shrieked. Gilfoyle grinned when he saw people turning to stare at her and how embarrassed his mom looked.
Quebec, 2008
Gilfoyle had been casually asking every single person he knew at McGill about their plans for the holidays. As much as he hated to admit it, he was terrified of being alone on Christmas. Not terrified enough to go home, obviously, but pretty terrified.
The one person who was also staying in the dorms over the holidays was a guy named Topher. He was weird, but it’s not like Gilfoyle could judge anyone for being weird. They’d agreed to spend Christmas together.
Gilfoyle took a big bong hit and then squinted at the TV. “It’s a Wonderful Life sucks my fucking balls.”
“Right?” Topher asked. “Why is a woman becoming a librarian the darkest thing they can imagine? Who’s that sheltered?”
“Yeah, she could’ve become an assassin or fucking something,” he said. He blew smoke out and said, “I wonder if my mom would be even more miserable if I’d never been born.”
“My parents would for sure be better off if I’d never been born. Guarantee,” Topher said. “The whole world would.”
“Yeah?” Gilfoyle asked. “You don’t seem that upset.”
“Well, you can’t live to make other people happy. That’s how you end up miserable,” he said. “You gotta live for yourself and the simple pleasures in life. I’m a Satanist.”
“What’s that like?” Gilfoyle asked, turning to him with interest.
“I could show you. My church is meeting later today,” he said.
“You guys do a Christmas service?” Gilfoyle asked with surprise.
“People have a lot of hate in their hearts on Christmas,” Topher told him.
Quebec, 2009 - December
“Happy birthday, Jesus. Sorry you’re not fucking real,” Charlotte said, raising her beer.
“Actually, babe, Jesus probably did exist,” Gilfoyle told her as he sat down next to her. “He just didn’t have magic powers or give a shit about humanity.”
He wrapped an arm around Charlotte.
“You’re so smart, babe,” she told him. She smiled at Gilfoyle affectionately and said, “You never, I never thought I’d fall for a college guy. Especially not one who does stuff with computers.”
“Well, you lucked out and got the total package. Satanist punk rock guy and future billionaire guy.” He kissed up her neck and she giggled.
“Do you miss your parents on Christmas?” she asked him.
He wrinkled his nose. “Christmas isn’t even real. It’s just Christians shitting all over pagans.”
She petted him and said, “It’s cool you know stuff like that. But, you didn’t answer my question.” She pouted at him and said, “I worry about you.”
He smiled and said, “Well, that just goes to show how much I don’t need my parents. I have you.”
She grinned at him and asked, “Am I a good mommy, Bertram?”
He nuzzled against her chest and said, “You’re the best mommy.”
Quebec, 2010 -- April
“You look great,” Gilfoyle told Topher as he watched him adjust his tie in the mirror. They were in a little back room in the Church of Satan, getting ready for Topher’s wedding.
“Thanks, man,” Topher said. “Thanks for being the best man ever. I hope you’ll let me return the favor when you marry Charlotte.”
Gilfoyle wrinkled his nose. “Marry? Oh. No. I love her, but I don’t--”
“You don’t really love her. Got it,” Topher said.
“What? No. Of course I do.”
“Sure. In that way,” Topher said.
“In that way? What the fuck is ‘in that way’?” Gilfoyle asked.
“She’s hot and fun to hang out with, so when enough time had passed you started saying that you love her. I totally get it. You gotta do something to pass the time in this fucking miserable mortal plane.”
Gilfoyle frowned. “Look, just because you’re ready to dive into marriage before we’re even out of college, doesn’t mean I have to do that to prove I really love Charlotte.”
“Alright. Sure. Fair enough. I’m just saying that you only love her ‘in that way.’ You’ll know what I mean when you met someone you love-love,” Topher told him.
Gilfoyle furrowed his eyebrows.
“Anyway, I should do this wedding thing,” Topher told him. “Hey, by the way, if you ever want to fuck my wife-- or me-- just say so. We’re married not dead, you know?”
Cambridge, 2013
“Why wouldn’t you want me to live with you in Boston?” Gilfoyle asked.
Alan sighed and pushed up his glasses. “Gilfoyle, man, I like you. I like you a lot. It’s been great being your roommate here in the dorms. I mean, you’re the coolest person I’ve ever met for sure.”
“Okay, so why wouldn’t you want to live together?”
“You’re the guy who’s cool to live with in college. You’re not an adult roommate.”
“How am I not adult roommate material?” Gilfoyle told him.
“You told me that you can’t sign a lease.”
“Only because my student visa is expiring!” Gilfoyle said.
“Making you an illegal immigrant. That’s another concern of mine,” Alan said. “You’re not eligible for a lot of real jobs.”
“I’ll find something. I always find something,” Gilfoyle told him.
“You’re also always high,” Alan said.
“And suddenly that’s a problem?”
“It’s like I said. You’re the guy who it’s cool to live with in college. But, I need to get serious about life.”
“I’m more serious about life than you are,” Gilfoyle said. “You’re going to move into an apartment that your parents pay for.”
“Yes, and I don’t want to explain to them that I’m living with someone like you!” Alan said.
“I’m at the top of our class. You barely passed and that was just because of me.”
Alan sighed. “You can move in with me, but if you ever can’t pay your share of rent, even once, that’s it, man.”
“Deal,” Gilfoyle said.
“And you can’t constantly be high,” Alan said.
Gilfoyle rolled his eyes and said, “Now you’re just being unreasonable.”
Boston, 2013
“Can I help you?” Brandon asked. He only opened his apartment door a tiny bit so that Gilfoyle couldn’t see inside.
“I’m your 3 o’clock,” Gilfoyle informed him.
“You’re not a hot girl,” Brandon said, frowning.
“Yeah and maybe someone who works in tech shouldn’t be catfished so easily,” Gilfoyle said, pushing past Brandon. “But, that’s only the first of many problems with your business.” When Gilfoyle saw the three women working in front of webcams, he politely nodded at each of them and said, “Ladies.”
“Dude, what the hell are you doing here?” Brandon asked him.
“I pretended to want to work here as a cam girl so that I could get an appointment to talk about the job I actually want. Keep up,” Gilfoyle told him. “You’re not making nearly as much money as you could be because your site can’t handle the traffic.” He walked directly over to Brandon’s servers and started looking at them. “Yeah, these are shit.”
“Get out of here!” Brandon said.
Gilfoyle ignored him as he started planning what he would do to increase the power of the servers. “Listen, I’m a graduate of MIT and we both know your site goes down every ten minutes. Just let me fix this.”
“If you’re really a graduate of MIT, why would you want to work here?” Brandon asked.
“I was sort of supposed to leave the country after I graduated,” Gilfoyle told him. “But, I don’t want to do that. I want to stay here and find a place to work that pays cash. And you need someone who knows what they’re doing but is willing to work for a shitty cam girl site. We both really lucked out. When you have a minute, can you get me more extension chord?”
Toronto, 2014
Gilfoyle looked over the car. “This has a lot of miles on it,” he observed. “I need something that’ll get me to the States. I hate being back in this frozen wasteland.”
“Well, there’s nothing I can do about the mileage,” the old man selling the car said.
“No, but you can take something off the asking price,” he said. “So, that when it craps out on me in the middle of nowhere, I’ll have some money left to get me to the States.”
“No offense, but you’re not very good at acting like you’re not desperate,” the seller said. “The asking price is it what it is.”
Gilfoyle sighed and took out the cash he’d brought. It was basically his entire net worth.
He got in the car and rested his hand on the dashboard as he softly said, “You’re all I have. Please be cool and get me to California.”
Palo Alto, 2017
Gilfoyle grinned as he watched Dinesh freak out over the apartment they’d just been shown. “If you like it that much, we’ll buy it,” Gilfoyle told him.
Dinesh smiled. “Are you sure? I mean, do you like it?”
Gilfoyle laughed and asked, “Do you care?”
“I feel like I should care,” Dinesh murmured.
“I like that it makes you this happy so I like it,” Gilfoyle said. He kissed Dinesh and then said, “Let’s go get this lease signed.”
Palo Alto, 2018
“You’re acting weird,” Dinesh said, narrowing his eyes as Gilfoyle looked around for their waiter.
“No, I’m not. You are,” Gilfoyle said.
“You’ve been nervous all night and also we’re at a very fancy restaurant instead of one of the two restaurants we always go to.”
Gilfoyle frowned and asked, “Did you want to go to one of the usual places?”
“Well, we already ate dinner, so no,” Dinesh said. “What’s going on?”
The waiter arrived with two glasses of champagne.
Dinesh furrowed his eyebrows and raised his glass, then spotted the ring in it.
Gilfoyle slid out of his seat and knelt down on one knee on the floor. “Dinesh Chugtai,” he said. “I love you so much. Will you marry me?”
“Fucking shit,” Dinesh said. “Holy fuck.”
Gilfoyle patiently waited for an answer that wasn’t just muttered swear words.
“I mean… yeah. I guess I want to marry you,” Dinesh said. “That’s weird, right?”
“I’m a little biased, but I’m going to say it isn’t,” Gilfoyle said.
Dinesh looked at the ring. “Is this a ring for a woman?”
“It was my grandmother’s. We can get it re-sized.” Gilfoyle squeezed Dinesh’s leg tightly and said, “I love you so much.”
“I love you too,” Dinesh reassured him.
Leicestershire, 2020
Gilfoyle had been worried about planning a wedding that was worthy of Dinesh, but he knew he’d hit it out of the park when he’d found the perfect castle in England for the ceremony.
He squeezed Dinesh’s hands tightly as they stood at the altar. He looked out into the crowd and saw his parents in the front row, which still felt surreal. He wasn’t sure what felt more strange: the fact that he’d invited his parents to his wedding or the fact that they’d actually decided to come.
Immediately after their vows, Gilfoyle kissed Dinesh hard. Dinesh softly said in his ear, “Asshole. You’re supposed to wait until he says ‘you may kiss.’”
Gilfoyle grinned at him and said, “I couldn’t wait.”
Palo Alto, 2024
Gilfoyle and Jared were having lunch together, which Gilfoyle had agreed to do once a week in exchange for Jared never bothering him outside of their designated monthly lunch time.
“Have you ever thought about fostering children?” Jared asked him.
“Not since the last time you asked me about that,” he said. “I’ve told you that Dinesh doesn’t want kids and I don’t want kids enough to find a new spouse.”
“But, have you even really asked him? You’re basing this on one conversation from before you were married,” he said. “And you wouldn’t be adopting. You’d just be fostering. Maybe for as little as a matter of weeks.”
“What’s your game here?” Gilfoyle asked him. “Why do you want me to do this?”
“These kids need it,” Jared said. “Horrible things can happen. Overcrowded state run homes, abusive families, some people end up in juvenile delinquent centers just because--”
“Back up. I can foster a juvenile delinquent?” Gilfoyle asked. “I was picturing tiny Jareds. You didn’t tell me some of them were little criminals.”
“They’re not that bad. Some just end up in juvie because they system failed them and no one--”
“Quit while you’re ahead. I’m willing to meet the delinquents.”
Dinesh and Gilfoyle led Carmen into their mansion. She looked around, wide-eyed. “It’s super fucked up that some people live in houses like this while other people have nothing.”
Dinesh frowned, but Gilfoyle grinned and said, “It is fucked up. Good observation. Come on, we’ll show you your bedroom.”
They led her up to her bedroom and then Gilfoyle asked Dinesh to go grab her bedding from the laundry room.
He turned to Carmen and said, “Hey, I’m sorry if my husband is making you feel unwelcome. I promise he’s on board with this he just has some problems with showing affection.”
“Don’t worry about it,” Carmen said. “But, uh, speaking of problems with showing affection, I hope you’re not expecting me to be too… Like, frankly, I’m really grateful about having a place to stay and everything but I’m gonna try not to get attached because… you know, most people don’t end up adopting. So.”
“Yeah, I get that,” Gilfoyle said. “Just treat it like you’re crashing here if that’s easier.”
She gave him a little nod. “Cool. Uh, thanks for everything, Gilfoyle.”
Palo Alto, 2025
The waitstaff finished singing “Happy Birthday” to Carmen and then walked away.
She took a bite of her cake and then said, “Thanks, guys, but it’s not my birthday.”
“I know, but we wanted to celebrate and they don’t have a song and cake ready for this occasion,” Gilfoyle told her.
She raised an eyebrow. “What occasion is that?”
“If it’s okay with you… we want to adopt you,” Dinesh told him.
“For real?” she asked. “Holy shit.”
Gilfoyle grinned at her and said, “For real.”
Dinesh nodded and repeated, “For real.”
“Of course it’s okay with me,” she said. She looked down and awkwardly murmured, “I love you guys.”
“I love you too, Carmen,” Gilfoyle told her.
“And I love you,” Dinesh agreed.
Palo Alto, 2027 - June
“Are you crying?” Dinesh asked, looking over at Gilfoyle.
“No. Fuck you. You are,” Gilfoyle said as he watched Carmen take her high school diploma.
“When she goes to college we’re going to be… empty nesters,” Dinesh said, wrinkling his nose.
“She’ll still be home over holidays,” Gilfoyle said.
“Still it’ll be weird…”
Gilfoyle smiled a little and put an arm around Dinesh. “Dinesh, do you want another kid?”
“I do,” Dinesh said, sounding a little surprised.
Gilfoyle wiped his eyes and tried to hide his own excitement as he said, “Well, Jared will be happy.”
When the ceremony ended, Gilfoyle and Dinesh found Carmen.
“We’re so proud of you,” Dinesh told her, pulling her into a hug.
“Thanks, dad,” she said.
“You showed high school who’s boss,” Gilfoyle said, grinning at her. “You ready to go buy a car?”
She grinned and said, “Hell yeah.”
Palo Alto, 2027 - September
“Do you need anything else?” Dinesh asked Matthew. “Glass of water? Another blanket?”
“No, sir,” Matthew said, pulling his blankets up over him. “This is perfect, Mr. Chugtai.”
“You don’t have to be so formal,” Dinesh told him affectionately. “Good night.”
When Gilfoyle and Dinesh were back in their own bedroom, Gilfoyle said, “He’s a real nerd.”
Dinesh grinned and said, “I know and he’s Pakistani. It’s perfect.”
Gilfoyle smiled a little and said, “I’ve never seen you take to anyone so quickly.”
“I just feel like it was meant to be. I think we’ll be adopting him soon. I mean…” He knocked on their wooden bedside table.
“I think so too,” Gilfoyle said affectionately before kissing Dinesh.
Palo Alto, 2028
“How are the kids?” Jared asked Gilfoyle.
“Matthew sincerely loves math homework. It’s adorable,” he said. “And it seems like Carmen is doing really well at California State. How are yours?” Jared opened his mouth, but Gilfoyle immediately said, “I’m joking. I don’t care.”
Jared laughed, knowing full well that Gilfoyle actually loved Jared’s kids.
“Hey, so uh…” Gilfoyle said.
Jared tilted his head, realizing with surprise that Gilfoyle was genuinely nervous.
“With Monica leaving, do you know who’s being considered for CEO?”
“There are several possibilities but it’ll be hard to find an ideal candidate,” Jared said. He tilted his head and asked, “Why?”
“This is gonna sound ridiculous and I don’t know why I’m even thinking it…”
“Oh my gosh.” Jared grinned. “You want to be CEO!”
“I know it’s--”
“Perfect!” Jared told him.
“Really?” Gilfoyle asked.
“Gilfoyle, you know how many times you’ve saved this company.”
“Yeah, but not with business type shit,” Gilfoye said.
“You’ve gotten good at the business type stuff,” Jared said. “I mean, you’ve grown and matured. I think the board should strongly consider it. I know Richard would love for it to be someone he knows and trusts. So, would Monica.”
“And you think I would be in the category of people they trust?” Gilfoyle asked.
Jared grinned and said, “I’ve never seen this side of you. It’s exhilarating having to reassure you.”
Tahiti, 2029
“This vacation house is so dope,” Carmen said as she set her suitcase down in the house they’d rented.
“When will the Internet be set up?” Matthew asked.
Dinesh put a hand on him reassuringly and said, “They’re setting it up now.” He looked between them and said, “Remember you need to get in lots of quality time with Gilfoyle during this holiday. It’s his last vacation before he officially becomes CEO.”
Gilfoyle wrinkled his nose and said, “If the new job keeps me too busy to see my kids whenever they need me, I’ll tell them to go fuck themselves and quit.”
Dinesh put a hand on Gilfoyle and said, “Please don’t tell anyone to go fuck themselves when you just became CEO.”
“Do you think I’d really do that?” Gilfoyle asked.
“I absolutely think you’d do that,” Dinesh told him.
Gilfoyle grinned and said, “Good, then I haven’t lost my edge.” He patted Dinesh’s back, then took Dinesh’s hand as he said, “Come on, kids, let’s go see the sites.”