Wingmen - Chapter 2
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 2! You might want to catch up on chapter 1 here:
“Ness!” Daphne cried as she entered the coffee shop. Vanessa waved at her and the two shared a greeting hug. “How are you!”
“Life is good!” Vanessa stepped away from the embrace but her smile remained. “I’m so glad to see you. How’s Northwestern treating you?”
“It’s great, I’m realizing how much I missed being in a library.”
While Vanessa was on a mission, she’d also been dying to ask Daphne about the little sabbatical she’d taken eight or so months ago. “You have to tell me about Costa Rica and the turtles.”
“It was ah-mazing. Let me grab a coffee real quick and I’ll tell you everything.” They entered the line together and Daphne explained the camp she had volunteered at to protect vulnerable sea turtles. It sounded a little too rough for Vanessa but she admired her friend’s passion for the work.
“Twelve weeks?” Vanessa repeated.
Daphne sipped her drink. “It was so good for my soul to take a break from work and the city and the stress. Taking care of those beautiful animals and soak up the sun and see the jungles.” Daphne smiled. “We had internet too, make no mistake.”
Vanessa chuckled. “Thank God for that.” She swigged her coffee before asking, “did people hook up in the camp ever?”
Daphne snorted. “I don’t think so. It’s a long hot day and by the end you’re pretty exhausted.” She drank. “Plus it’s pretty isolated. Imagine if it was bad and you’re just stuck?” Daph made a face and Vanessa chuckled. “How’s work?” Ness made a face of her own. “C’mon, what you do is interesting!”
Vanessa rolled her eyes. “I think you like my job more than I do.” She told Daphne a little about the clients she’d been servicing. A few patent submissions. Some licensing deals. “We might go to trial over a pop song copyright dispute.”
“Ooh. Anything I would know?”
Vanessa smiled mischievously. “Can’t say. But yes. Oh, stop getting excited. These things usually get solved with a check.” She gestured with her cup. “Your turn.”
Daphne swallowed a sip. “Not much different from when you were there.” Daphne had just begun working in the law library when Vanessa was halfway through law school. Their constant run-ins had turned into a close friendship, and they’d stayed in touch despite the both of them bouncing around the country for the last decade or so. “Kinda weird calling it Pritzker now,” Daphne continued. “But it was like picking up where I left off.”
Vanessa dredged her memory. “Is…what was her name…the grouchy one? Is she still there?”
Daphne brightened as she remembered. “Grouchy Gretchen! No, she retired a few years ago I guess. She actually made the best carrot cake if you can believe it. So good.”
“At least she could do something nice,” Vanessa muttered.
Daphne chuckled. “Those were the days.” She became a little more wistful and met Vanessa’s gaze. “You and Stuart. I’m sorry that didn’t pan out.”
Vanessa stiffened, mostly by reflex. The pain had long since subsided into an almost-fond emotional scar. Stuart was her longtime boyfriend and she’d planned on marrying him after they’d graduated. Almost did. But one day it had hit her that she was really just going through the motions. Stuart was great and she would always love him. But she found she didn’t need him. So she’d let him go.
“He’s happy, I think. Silicon Valley still.” She shrugged. He’d been married and divorced in the interim. He emailed every eighteen months or so swearing to catch up. They’d exchange a few messages before becoming strangers again.
Vanessa deflected her memories. “Who was your last serious relationship? Imon?”
Daphne fluttered her fingers. “That wasn’t very serious. He was sweet, though.” The edges of her eyes crinkled. “Jason was.”
Oh shit, right. Jason. The one who’d nearly ruined men for Daphne. He’d broken up with her after meeting someone else.
Vanessa cleared her throat and went for a less-than-graceful segue. “You’re not seeing anyone now?” She knew the answer was no, according to her instagram research. Well, so she hoped. Daph shook her head, and her sardonic smile told Vanessa she knew what was coming next. Daphne was sharp. That’s why she was perfect. “I have a friend you should meet.”
Vanessa could sense her friend’s protest and quickly pulled up the photo of Darren she’d carefully chosen. Him in a suitcoat, smiling at some charity gala. “Darren Tipton.” She said, handing her phone to Daphne. Vanessa was pleased to see Daphne’s eyebrows rise slightly. “He’s a copywriter at Macpherson & Slade. Well, creative director now,” she corrected. “Texas boy.”
Daph’s amused expression became a little mischievous. “Cowboy? Does he have the cute accent?”
Vanessa smiled. She had her. “No, he took a radio class in college and they ‘trained it out of him.’ I’m sure he’ll tell you the story.”
Daphne snorted. “Who says I’m meeting him?”
Vanessa’s posture said “oh come on.” She gestured at the photo. “He’s one of my best friends. He’s great, and a perfect match for you.”
Daph handed the phone back. “Okay. So what’s actually wrong with him?” Meaning: if he’s so great why’s he single?
Vanessa wracked her brain. “He’s pretty emotionally stable. Well, for a guy. He reads books! I think Hemingway’s his favorite?” That always seemed like a ding to Ness but Daphne didn’t seem bothered. She needed real dirt. “He was practically engaged for like five years. She was a doctor. Something medical, anyway. They both worked too much and things sort of fell apart. I think that’s Darren’s problem. He puts too much into his job.” Vanessa held up a finger. “But! But! He’s been going to therapy and is seriously working on his work life balance. I can attest to that.”
Daphne sat back and folded her arms. “Did you date him?”
Vanessa shook her head. “Nope. We met through work. One of his clients needed a bunch of consultation on IP and we became buds. A few late nights going over contracts and patent filing is a great way to bond.” Vanessa smiled. “As you know.” She spread her hands. “We’ve never been mutually single, so….” She trailed off as if that explained it.
Daphne laughed, but Vanessa could see the challenge in her expression before she asked the question. “So if he asked you out right now, you’d say no?” Her eyes glittered with amusement. “You are single now too, aren’t you?”
Vanessa considered a moment. “There was a time maybe. Now?” She shook her head. “We’ve been friends so long he feels like a….” Brother wasn’t quite right. “Like a step-brother. Technically in bounds but still wrong.” She laughed at her own analogy. “You know?”
Daphne seemed to accept it. “Alright, fair. Well, I have an idea.” She rummaged in her bag and produced a deck of Tarot cards. “The cards will decide.”
Vanessa shook her head, bemused. “Since when do you do Tarot?”
Daphne shuffled the deck. “It’s a new thing I’m trying. I saw these at the bookstore and thought ‘aw what the hey.’” She held the cards out. “Pick one.”
Vanessa hesitated. “Don’t I get to cut it first?”
Daphne nodded. “Sure, whatever.” Vanessa split the deck and pulled a card. “Two of cups.”
“What’s it mean?” Vanessa asked.
Daphne was sheepish. “I have no idea. Pick another one.” Vanessa laughed but grabbed a second card. “Okay the Page of Wands. Wands are like discovery and creation so….”
“Well that seems positive?” Vanessa hazarded.
Daphne laughed and shrugged. “This was a bad idea. Try one more. Oh! Death! Great!”
All of Vanessa’s plans ruined by an unlucky card draw. Well, she’d been thinking of backups in case Daph didn’t want to give Darren a shot. Mayra or maybe Anjali.
“Death means transformation. Starting new cycles.” Daphne explained as she put her cards away. “They say to do it.” Vanessa understood the wisdom of letting Tarot decide. You had someone to blame if it turned out miserably. Or you could pretend it was fated after all.
“You’re gonna like him.” Vanessa said. “I told him it’s a blind date. How do you feel about French food?”
Daphne swooned. “Oooh fancy.”
“Perfect! I’ll coordinate with him. And get back to you.” Ness smirked. “Free food at least.”
Daphne slapped the air in front of her. “He better not be super lame.”
Vanessa gasped melodramatically. “That would be so tragic.”
“Okay,” Daphne said,, “now that you’ve tricked me into this setup….” She ignored Vanessa’s innocent face. “Let’s have a real hang.”
Vanessa considered. “There’s that new wine bar…?”
Daphne bobbed her head. “Don’t hate it. I also kind of want to just order a pizza and make margs. Bring Elena and Trish like the old days.”
Vanessa shook her head. “Elena’s in Europe. Some guy she met over there in Portugal. Don’t ask. But Hae-Lee’s still around.”
Daphne smiled as she remembered. “Oh little Hae! She was so quiet, and then we got her to do-“ Daphne’s eyes widened as she came to the conclusion. “Karaoke!”
Vanessa laughed. She’d always hated the idea of karaoke until that night. She’d only been once or twice since. It would be good to get the girls back together again. She and Daphne had been particularly close before life separated them. Whatever happened with Darrenl she promised herself she’d keep the vivacious librarian in her life.
The two women hung out in the coffee shop reminiscing while the dregs of their coffees cooled to unlikability. They sketched out a haphazard plan together, one of those plans that starts with “we should” and sounds fun on paper but never happens because adulthood gets in the way. Vanessa had more confidence in this one because Daphne was organizing it, and she got shit done. But still.
After maybe an hour, Daphne excused herself. “Tina-“ her sister “-is flying in with her wife and boys tomorrow. I need to clean my apartment.” She made an unenthusiastic fist pump. “They’re staying with Kaia’s parents, thank God. I love my nephews, but I also really love silence.” She smiled, but it was guilty.
Vanessa hugged her. “Well say hi to everyone for me. I’ll text you about Darren.”
Daphne saluted. “Should be fun. Chat soon. Great seeing you!”
They parted ways, heading in opposite directions. Vanessa fished her phone out of her purse. “What are you doing Friday night?” she texted Darren.
The bubble with three dots showed up right away. “Have a pitch in the afternoon then will probably need a drink and to kick your ass in pool.”
As if, she snorted. “How about a date with a hottie?”
“Well someone has a high opinion of herself,” he replied.
She sent three eye-rolling emojis. “It’s my friend Daphne. You’re taking her to Le Bouchon.” A second later she sent. “But yes, I am also a hottie.”
“I didn’t think you actually had anyone in mind. I’m impressed.” Before she could reply he said, ”can I at least see a photo of this person?”
“Wow shallow much? You’ll like her.” But she decided she’d send one. “You have to promise not to do background research!”
“Scouts’ honor.”
Vanessa found a flattering selfie on Instagram and zipped it over. She wished she had shown him in person so she could gauge his reaction, but she so knew his taste. Daphne’s keen eyes alone would get him even if her annoyingly tight yoga body didn’t.
“She’s lovely,” he replied simply and she assumed be was playing coy. “What time?”
“I’ll make you a reservation and she’ll meet you there. I’ll send the invite.” She had a connection over there and was confident she could get a slot. A short phone call later she had it arranged. “7:30, under Tipton. There’s a reason I chose Le Bouchon.”
She knew that made him laugh. “Yes, Ness, Paris. I got it.” A second later he sent, “I won’t make you get Korean BBQ. You don’t deserve it anyway.”
Oh please. “You’ve got nothing don’t you!”
“Hush. I just need to cross some eyes and dot some tees. My guy has a complicated schedule.”
“Sure,” Vanessa texted back with several U’s to underscore just how convinced she wasn’t. She thought maybe that would be the end of the conversation but as she climbed on the L Train, she sent another message. “You actually have to try to like her. You can’t just pass on her to win the bet!”
“HA!” he answered a few minutes later. “Losing confidence already. My mind is open, Ness. I promise to play within the spirit of the game.” Boys and their sports metaphors.
“You better!” she demanded and he responded with a heart. She grinned. This was so in the bag. She swiped over to her conversation with Daphne, and continued orchestrating her masterpiece.


I love the playfulness and hidden tension already. Can’t wait for Chapter 3!
This is so fun! I would watch this movie! 🎥 🍿