Wingmen - Chapter 3

Vanessa and Darren consider themselves expert matchmakers. Now, they're taking on their hardest challenge yet: finding the perfect match for each other.

If you’re just joining us, this is chapter 3! You might want to catch up on previous chapters here:

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Darren felt the vibration in his desk before he noticed his phone was ringing. He tapped to answer.

“Tipton!” Luke said before Darren could speak. “I’m getting on the treadmill and don’t feel like texting. What’s up buddy?”

Darren smiled into the receiver. “You can just call me later. It’s not that important you know.”

“All good man, I was thinking of calling you anyway.”

Darren pursed his lips thoughtfully. “Oh yeah?”

“Yessir,” Luke replied. “Buddy of mine invited me to a golf outing next weekend and we need a fourth.”

Darren grimaced. “You know I’m not any good.”

Luke didn’t pull a punch. “Yeah I know, but you’re a good hang. It’s for charity. My buddy’s semi-pro or some shit and is gonna carry us anyway.”

“You know what, put me down for it. Or whatever.” Darren considered a moment. “I probably gotta Venmo you something huh?”

He could hear the smile in Luke’s voice. “I’ll send you a request.”

“Great,” Darren said. “I better get out to the driving range.” For all the good it would do. He found when he was trying to set people that the best thing to do was to just cut to the chase. “So listen, I have a friend I think you should meet.” Trying to dance around and feel it out didn’t make it any less awkward to be like “hey date my friend.”

“Oh shit!” Luke said with half mocking amusement. “Am I getting Darren match made right now?”

“Screw you,” Darren said, grinning into the receiver. “But yes. One of my best friends, she’s great.”

Lucas Palazzo was a bit like Darren. He worked a little too much to sustain a serious relationship. He also liked to travel and enjoyed the single life. But about a year ago, they’d been hanging out together and as Miranda has wandered off to the bathroom, Luke had said, “Someone a little more constant would be nice.” He’d smiled a little wistfully and nodded after Miranda. “Like her.”

She and Darren split up something like two weeks later. Seventeen days if anyone was keeping track. But Darren and Luke had grown closer in the following months. A lot of baseball games and sports bars. Darren was always on the lookout for a good woman for Lukey, but it was a challenge. Luke was picky.

Like Ness. Or, as they both would say, they had “high standards.” They were either going to love each other forever or absolutely hate each other.

“Vanessa Shen. She’s a lawyer.” Luke winced audibly, mostly a teasing noise but Darren explained, “It’s intellectual property. Patents and copyright stuff.”

Luke doubled down. “Ah so she works for like the RIAA right? One of those people bleeding starving artists?”

Darren scoffed. “You should lead with that, she’ll love it. Anyway stop shooting this down.”

Luke laughed. “Sorry, I’ll stop. She from Chicago?”

Darren shook his head even though his buddy couldn’t see him. “Nah, she was raised in Fresno, but went to Northwestern for law school. D.C. for a bit but she’s back here. Met her through work.” He saved Luke from asking the question he was tactfully avoiding. “She’s pretty. Loves to run and secretly likes tennis.”

Luke chuckled. “Secretly?”

Maybe Darren shouldn’t have given this away but he had to explain now. “Oh, like sets an alarm to watch the Australian Open kind of thing. I guess she had a thing for Nadal.”

“He is pretty dreamy,” Luke agreed. He also caught on quick. “I’ll let her reveal it in time.” Luke took a beat before asking. “Alright nobody’s perfect. What’s her deal? She gotta weird laugh?” He pitched his voice with condescension. “Is she a Cubs fan? I mean I guess it’s okay if she’s a real fan,” Darren could practically hear Luke make the air quotes, “but if she’s one of those fans who likes them for the vibe or whatever….”

Darren cut off the rant. “She’s not a Cubs fan. She doesn’t even really like baseball that much. But I got her tickets to a Blackhawks game and she had a good time.”

“Alright I can work with that,” Luke said like he was chewing on a thought. “So we have this hot, smart lawyer who’s down for hockey and you’re not dating her because…?”

“Ah man,” Darren sighed. It was a common question when setting people up, especially when you were single yourself. “She was one of my first friends when I moved up here. She was engaged to some other guy. Then Miranda….” He trailed off because he didn’t want to go down that road. Luke grunted in a way that said he understood, so Darren went on. “We just have always been comfortably platonic. She’s a great friend. Brutally honest and tenacious.”

Luke chuckled. “Marketing guys. They know how to make a tough woman sound appealing.”

Darren laughed with his friend. “Hey, for the record I never said tough.” He softened. “But you know…the tough ones are the good ones.”

While Luke muttered something along the lines of “that’s true,” April, Darren’s project manager appeared in his office doorway. She knocked on the frame while she cradled a laptop in her other arm. She smiled and mouthed, “You coming?”

Darren held up a finger, nodded, and gestured for her to go on. He’d be along. “Hey bud, I gotta head into a meeting. I’ll check with her for a good time and-“

“No, no, don’t play middleman on me,” Luke interrupted. “Tell her you’re going to give her my number and I’ll set it up.” Damn. Ness was gonna like that. Luke’s tone was wry when he added, “And if she somehow declines a chance to meet me, no harm no foul.”

Darren gathered his stuff for his pitch planning meeting. “On that note, you don’t have a clown fetish do you?”

“Listen, I’m not one to kink shame but, if she’s into that I’m not sure I could-“

Darren laughed. “No, Jesus, sorry. It’s not her thing either, but the last guy I tried to set her up with? Yeah she found out the hard way that he was.”

Luke laughed too. “No! So, I have a red nose around here somewhere….”

Darren winced. “C’mon man, I could use the W here.” He reached for the meeting room’s handle. “Alright, I really have to go.”

“Sure thing, man. Talk soon!”

The connection died and Darren took a seat at the table. Most of his creative team was there.

“Who was that? Your girlfriend?” April drew the word out like a schoolyard taunt. Several of the people in the room chorused “ooooh!” in a similarly teasing way.

Darren rolled his eyes and played his part as the offended party. “Wildly inappropriate.” Someone booed. Someone else threw a wad of paper at him. “I was setting up my buddy on a date.” The coworkers who had “ooooh’ed” repeated the noise. Darren joined them this time and slapped his hands to his face.

“Okay, enough of that. Let’s talk potato chips.” He paused. “Actually you guys want some lunch? I’m in the mood for Korean barbecue.”

---

“He wants to ask me out himself?” Ness said. Her tone was outraged but Darren knew that for the defense mechanism it was.

“Uh huh,” Darren said cutely. He had her on speaker phone while he chopped some chicken. “Do you consent to me giving him your number?”

“How often do you write that on your marketing forms?” Vanessa teased.

Darren rolled his eyes. “Stop deflecting, Ness.”

He heard her scoff. “Tell me more about him first.”

“I met him through work too. He used to date one of our photographers. He’s a physical therapist. Likes to run 5ks and half marathons.” Darren emphasized this last bit because it was one of Ness’s favorite things to torture herself with. “He’s also in an indoor soccer league. I think he’s pretty good.”

“Soccer? Really?”

Darren rinsed his hands. “What’s wrong with that?”

Vanessa chuckled. “Nothing really, just making you sweat. You’re gonna have to give me more than this, though.”

Darren rolled his eyes at his phone. “Yeah I’m sending you some photos shortly. He’s a good dude. He took me to a bunch of White Sox games after Miranda.”

“Oh, Baseball Bro!” Ness said, realizing.

“Yes, my friend Luke,” Darren replied with growing exasperation. “I have brought him up often.”

“You know I can’t keep them all straight,” Vanessa said.

Darren found a couple photos and texted them to her. “I keep all your people straight,” he muttered. “I sent you some pics. Let’s see…he likes Dave Matthews, but also likes jazz. I think he can play guitar but only in the woo girls in college kind of way.”

Ness snorted. “Is that a selling point?”

Darren considered. “Yeah it’s the cute but not douchey kind.” He decided to move on. “I think his favorite show is The Wire but he also has weirdly deep knowledge about One Tree Hill.”

“I love that show!” Ness said. Before Darren could remind her that, yes, he knew, she got the photos. “Whoa this is him? He’s actually pretty hot. You’ve been holding out on me?”

Darren smiled at his phone triumphantly and was slightly annoyed she couldn’t see him gloat. He played casually for now. “He’s been somewhat unavailable lately. Plus I wasn’t sure you were worthy of him.”

Vanessa gasped. “What’s that supposed to mean!”

Darren crossed his arms. “Just that. He’s one of my best buds and he deserves the best.”

Vanessa played along. “Okay, how dare you. I’m awesome.”

Darren considered doubling down, but he knew a little too much ribbing could cause her real annoyance and he backed off. “Yes,” he agreed, “you are. He just lives way on the south side and he was kinda seeing this girl for a bit. Timing’s right now though.” He got serious. “He’s charming, and smart and funny. I love you both and I think you’ll enjoy each other. Really.”

His sincerity usually wore her down and this was no exception. “Oh, alright, you can give him my number. I’ve been kind of wanting Indian food if you want to nudge him—“

Darren interrupted her with a loud sigh. “Indian? That’s not good first date food, cmon Ness.”

She parroted his sigh. “You literally said you loved me like two sentences ago and now you’re denying me my naan. Mixed signals Dare-bear.”

He smiled but kept his tone annoyed. “I’m sure you’ll live.” He glanced at his skillet. “Hey so speaking of food, I’m making stir fry now. You wanna come for dinner?”

“That sounds good,” Vanessa said. “But I’m going for dinner with my work fam imminently.”

“Imminently?” Darren mocked.

“Oh shut up. Yes, imminently. As in, I’m in the elevator now.” Her voice was tinged with wickedness when she said, “We’re getting Indian.” He heard a soft ding. Then a muffled “just a sec!” before Ness’s voice returned. “Gotta go. Daph! 730 Friday!”

Darren snickered to himself. “I’ll miss my own funeral before I miss it.”

“Mwah!” Vanessa said before hanging up.

Darren texted her immediately. “So I gave you all kinds of great dirt on Luke. You could send me a few notes on Daphne.”

She replied less than a minute later. “I could!” Followed by several thumbs down emojis. So much for that.

He opened a conversation with Luke. “Yo here is Ness’s contact. She’s game.” He zipped her details over and got started on his dinner.

He was almost finished cooking before Luke replied. “Thanks man. Looking forward to it.” He’d also sent a Venmo request for the golf outing. Darren muttered that it had better be a good charity before paying it.

He sat down to dinner and pulled up the photo of the mysterious Daphne. He thought about looking her up but decided to resist. She did have pretty eyes. They looked brutally honest and tenacious.