Wingmen - Chapter 1

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

“I’ll have what he’s having,” Vanessa said as she claimed the stool. She glanced down to see what she’d just committed to. “You ordered that just to piss me off, didn’t you?”

Darren smiled. “If it’s any consolation, I don’t like it much.” He studied the label. “I think you’ll actually like it, Ness.”

The bartender popped the cap and set the bottle on a coaster in front of her. “Tab?”

Vanessa inclined her chin at him. She and Darren clinked their bottles together, a casual toast. “Happy Friday,” Darren said.

Vanessa took a sip and felt a twinge of annoyance. “This is really an IPA?” It was as close as she’d come to admitting he was right.

He had the decency to not wink, even though his smile was a little smug. “How was work?”

She let out a frustrated breath that wasn’t quite a raspberry. “Work.” She wasn’t in the mood to discuss it. She had better news. “Guess what?”

Darren raised his eyebrows as he took another sip. “Let’s see. You...got a new washing machine?”

Vanessa rolled her eyes. “No. This is actually exciting.” He surrendered by spreading his hands. “Melissa and Pete just got engaged!”

Darren leaned back on his stool and appraised her with a knowing smile. “You’re kidding.” He wasn’t as disappointed as he was supposed to be.

“Oh my god.” Vanessa blinked. “You already know.”

His smile became a little more real. “I’m friends with Pete too. Saw it on Instagram.”

“I can’t believe you’re stealing my thunder right now,” Vanessa said as she took another sip of the IPA. It was actually pretty decent. She brightened a bit and went in for the kill. “Pretty sure this puts me ahead.”

Darren’s smile was coy but she knew how competitive he was. He was trying to be a good sport but she could see how incredibly annoyed he was. “Are you?” It came out casually enough but she was beyond pleased to have gotten his goat.

“This make three proposals, one of which has led to marriage. Seventeen long-term relationships and...who knows how many third dates. At least a hundred.” Her grin glinted ferally. “Maybe two.”

Darren sighed. “I thought we weren’t keeping track of third dates anymore.”

Vanessa chuckled. “Maybe we should so you’d still have a chance. Besides, I seem to remember you wanting to,” she cleared her throat and threw her voice deeper, imitating him, “stop tracking ‘em because it was ‘too hard’.” She poked him on the shoulder, teasingly. “Admit it. I’m the better wingwoman.”

He wouldn’t. “We went over that as well. Too many syllables. And no! Wingperson makes it sound like you’re chicken wing fan.” He took a sip. “Wingman is ungendered. It’s fine.”

“Nice deflection.” She turned to face him a little more directly. “Admit it.”

He’d never cede that she was a better matchmaker than he was. They’d had this little competition between them for a few years now, seeing who was better at setting up their friends, coworkers, and odd random strangers. At some point along the way they started keeping score. And now Vanessa was winning.

“You know,” Darren said, and she preemptively rolled her eyes. “You’ve got more cheaters in your history than I do.”

“First of all, men suck, so that’s not my fault.” She took another sip. “Second of all, that’s not a rule. Nice try.”

He spread his hands, probably the best concession she’d get out of him for now. But he surprised her. “Put her on my tab,” Darren said to the bartender.

She hid her astonishment with a boast. “I’m gonna make you regret that.”

Darren shrugged. “Whatever you say, lightweight.”

Vanessa pretended to be offended, but her days of heavy drinking were mostly behind her.

Darren nodded at the bartender. “Get her another one.”

The bartender raised his eyebrows a fraction. Vanessa shrugged. He and Darren traded some kind of look. Men.

“Alright,” Vanessa said. “How about I kick your ass in pool?”

“Sure, I’ll let you think you can win at that too.” Darren gestured for her to lead the way.

She scooped her new bottle and they went over to their usual table. Vanessa broke. Darren always insisted she go first on the first game. Then loser broke. “The brunette over there keeps looking at you,” she said as he lined up a shot.

“I know.” He was unfazed by the minor distraction. “Solids.” He moved to line up another shot.

“C’mon. She’s your type: woman!” Vanessa snickered at her own joke. Darren missed sinking the orange ball and gave her a look somewhere between amused and annoyed. Vanessa lightened a little. “Cute brunette with glasses? That’s three of the five boxes.”

“She’s still in college. Pass.” He gestured at the table. She wondered if maybe she was pushing a little too hard. It’d been over a year since Miranda and he finally seemed to be interested in dating again. Maybe not.

Vanessa lined up. “You gave me such a shitty shot.” The cue ball clacked off her target and she almost sank it anyway. “You don’t know that she is.”

Darren shot her a look. “Kappa Kappa Gamma hoodie? C’mon.” He winced as he missed a shot.

Vanessa shrugged, sipped. Sank her shot. She looked at him closely and he wasn’t terribly readable. Time for a little push. “Dare ya.”

He grinned. “Trying to juice your numbers?”

She sank another shot. “Kicking your ass all over the place tonight, Tipton.”

He snorted. “Bet I can find you a better match.” It was good to see the fire in his eyes.

She missed on her third. “In this dive? Please.”

He shrugged. “I can do better than ‘frat boy’. Though if you’re interested, little Timmy over there keeps checking out your ass.” He sank a ball and nearly scratched.

“Who isn’t?” Vanessa said, looking around for the boy he’d mentioned. It felt a little good to know a twenty-two year-old was drooling over her even if it was also gross.

“Actually,” Darren said more thoughtfully. He stopped lining up his shot. “I know the perfect guy for you.”

Vanessa glared. “Like the last one?”

Darren spread his hands. “Look, I didn’t know about the clown fetish, okay? I said I was sorry.” He smiled but managed not to laugh. “This one’s good.”

She scoffed. “Yeah, okay. Will you go already?” Did he really think he could set her up with someone? She’d been kind of thinking the same thing about him. Her friend Daphne...Darren would love Daphne. She was practically certain.

Darren missed his shot badly. “Too scared I might be right?” He teased.

She narrowed her eyes at him. “Absolutely not. In fact, I have someone in mind for you, too. My best match yet.” He laughed but she could see he was a little intrigued. He often said she had good taste. “Guess we’ll see who the best wingman really is, huh?” She shot him a sly smile.

He held out his hand. She loved when he got serious. She shook it. “Now go get me one more drink. This time--”

“Yeah a vodka-diet.” He stuck his tongue out at her. “Lime?”

She was half annoyed he could kind of read her mind. “You tell me.”

He shrugged. “Last time you didn’t want the lime because you said it got the lime in the coconut song stuck in your head. I wasn’t sure if that was a one-time thing, or..?”

“Get me the damn lime, Darren.” She said and shooed him away. She took her shot and missed. He would accuse her of cheating when he got back. He always did. She leaned on her stick and watched him. He said something to the brunette with glasses. She laughed. He laughed. He ordered the drinks. The college girl laughed again, and put her hand on his forearm. Satisfaction bloomed in Vanessa’s chest as she realized her intuition was right.

She didn’t even try to hide her smugness when he returned. “Let’s see…sociology?”

Darren shook his head as he handed her the drink. “Molecular biology. Grad school.”

Vanessa clinked her glass against his plastic cup of water. “So? Grad school means she’s not THAT much younger.”

Darren rolled his eyes. “I have a 401(k). She has a thesis. Different worlds.” He studied the table. “You cheated didn’t you, Ness?”

“As if I needed to. Hurry up,” she teased.

She ended up winning this game too. Darren lost gracefully, seeming to have accepted that tonight wasn’t going to go his way. “Alright, tell me about this girl you have for me.”

She took his water and sipped. He didn’t protest. “Nope. I’ll set it up but you’re going in blind.” He grimaced. Darren hated blind dates. “Trust me. I wanna be best man at the wedding, by the way.”

He took the water back from her. “Fine. But if it goes poorly you’re buying me a nice steak dinner.”

Vanessa snorted. “Yeah, okay.” She stole the cup and finished the water. She chewed one of the ice cubes. “When your shitty match doesn’t work for me, you’re flying me to Paris.”

She was pleased to see his eyebrows shoot up in surprise. “Shitty match?” She loved that’s what he objected to. “You’ll love him so much, you’ll ask me to officiate.”

Vanessa handed Darren the empty cup. “My brother would kill me if he didn’t get to do it.” Vanessa made a thoughtful face. “You can be flower girl though?”

Derren grinned and held out a hand to seal their second wager.

Vanessa quirked a brow and felt a stab of guilt. “You’ll really fly me to Paris?”

Darren’s eyes glittered. “I’m certain it won’t come to that.” His grin shifted a little more wickedly. “Plus the steak you’re gonna buy me is in Korea.”

Vanessa refused to let him see her cringe. She shook his hand. “You’ll have to get it on your honeymoon, Dare-bear.” He hated that nickname. Well, he pretended to at least.

He checked his phone. “I better settle up and head home. You good?”

Vanessa nodded. “Yeah, I’m set.” She unlocked her phone. “I’m going to head out too.” It was still before midnight but it had been a long week and she wasn’t in her twenties anymore.

Darren went to the bar while Vanessa lingered near the door. She watched the college girl steal glances at Darren. Vanessa would have insisted he pursue that if she hadn’t committed to the wager. The girl made eye contact with Vanessa and she gave the student a knowing look. As Darren approached, Vanessa said, “Ready, sweetie?” Vanessa winked at her.

Darren chuckled when they were outside. “Protecting me?”

Vanessa poked him in the ribs. “Protecting my trip to Paris.” It was really more about putting a younger, prettier girl in her place, but he didn’t need to know that. “My Uber’s almost here. You don’t have to wait.”

He shrugged. He always waited. “I’ll talk to your guy and set something up for next week?”

“My guy?” She snorted but her interest was piqued. “I’ll find time for you to go to dinner next week. Don’t make that face. I am so right about this.” Her ride approached.

“Text me when you get home, alright?”

Vanessa scoffed. “Okay, Dad.” She was touched that he frowned. “I will,” she promised.

He closed the door behind her and waved. As the Uber pulled into traffic, she scrolled through her contacts. Daphne Jansen. Vanessa opened a new text message. “Daph! It’s been a bit. How are you? Free to grab coffee this weekend? I’d love to catch up.”

She sent it and wondered about what Darren had up his sleeve.