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Rated: 13+ · Short Story · Romance/Love · #2259069
An old friend, a new potential love, and an unforgettable night out.
Every guy needs a solid wingman. Someone who can put their ego aside to hype up your most mundane talents and accomplishments, or put in a good word and a friendly gesture in your direction on a hopeful night out. Wingmen give us courage. They lift us above our doubts and insecurities and make us believe for the briefest moment that we are the right guy for a certain special someone, that we actually are a pretty good catch. Chris was our wingman, and easily the most beloved member of our little group. He’s been with Gabby since the second week of middle school when they bonded over their shared awkwardness of trying to march and steady their trumpets without falling and cementing their status of stereotypical band-geek losers in a sea of merciless, unforgetting pre-teens. Chris and Gabby were the paragon of millennial monogamy.

Chris never complained about his relationship with Gabby. He only occasionally lamented over never having really been a participant in the dating game. He never locked eyes with a girl across the cafeteria and had to ask a friend to go ask her friend what she thought of him. He never walked into a bar and wondered if he would be sleeping in someone else’s bed that night. He never cropped an eighteen month old photo of himself where his hair was just right and debated internally whether he was being too enthusiastic about his love for hiking and dogs as he copied and pasted his profile into yet another new app.

Despite attending college three states apart, Chris never felt tempted to stray from his lifelong commitment to Gabby. Instead he played the field on our behalf, striking up conversations with women everywhere he went, always making sure to mention that he had a friend who he thought would totally hit it off with them. He would say he knew a guy who was currently obsessed with the band on a girl’s t-shirt and ask if they were playing nearby anytime soon. If he saw a rack mounted to the roof of her Subaru Outback, he would tell her that his poker buddy was looking to get into kayaking but didn’t know where to start. He never lied, either. That’s what made us love him so much. It was never about numbers with Chris, never about helping us add notches to our belts. Every proposal on our behalf came from a genuine belief from within that he was helping us each find “The One.” Chris’ devotion to matchmaking is how Rob and Mark eventually met their wives, and his repeated efforts to play cupid for Jeff is what led Jeff to discover that he’s actually not into women at all.

When it came to me, Chris always seemed unsure of himself. In college he guided me through the motions of introducing myself to Julie, the girl at the independent cinema in town who had been taking my tickets every week and saying things to me like, “Oh this is a good one! I think you’re going to like it.” Julie and I became good friends in our sophomore year and spent countless weekends in the winter of 2009 over whether Quentin Tarantino was too full of himself to be considered one of the all time great filmmakers.

My friendship with Julie was everything it needed to be at the time. We were two film nerds who spent our youth in middle of nowhere suburbia digging through our local Blockbuster for anything David Lynch or Kurosawa, longing for the day that we could discuss these films with another sentient creature. We were each other’s living embodiment of IMDB, constantly one-upping each other with things like, “Well did you know that Marlon Brando wasn’t supposed to hold a cat in The Godfather, but Francis Ford Coppola found a stray in the lot and thought it would be perfect for his character?” Or “Sean Bean was so afraid of flying that when he was filming The Lord of the Rings, he actually climbed the mountain in full costume because he couldn’t bring himself to get on the helicopter.”

Although happy that I had made a friend, Chris was confused about my specifically singular relationship with Julie. Over the years he introduced me to several more women, all of whom were good matches on paper, and some who I still keep in touch with to this day, but none who led to a lasting relationship. I often felt like I was letting Chris down, or that he thought I wasn’t taking his help seriously. I wanted there to be fireworks like when he introduced Rob and Mark to their future wives, but the most I ever felt was the dull fizzle of a new hobby buddy.

There was a brief hiatus in Chris’ involvement in our love lives when he and Gabby celebrated the birth of their twins in the summer of 2012. Once they were potty trained and sleeping on a consistent schedule, and he had the first quiet moment to himself in years, Chris felt the pang of unfinished business with my romantic pursuits. He messaged me shortly after my twenty-seventh birthday, buzzing with excitement that he met a woman at the hospital he worked at who was my “dream match.” Normally so forthright with details of his potential partners, Chris was oddly tight lipped about this new match. All he would tell me was that her name was Amy and she was new to the area. “Trust me, bro. This is my magnum opus.” He was so overjoyed to have a reprieve from the world of Bob the Builder and sippy cups that he took it upon himself to make reservations for us at Riviera, a new and highly reviewed restaurant a couple stops away from the hospital.

As I stared at myself in the mirror of my locker at Framework Focus on the night of the big date, my first in nearly six months, I considered the effect of my first impression. I could hurry home and change into a nicer outfit, but run the risk of arriving late and coming off as a guy who can’t be relied upon to be punctual. Or I could keep my grey khakis and navy blue short sleeve button down and try to lean hard into the idea that I’m just a super casual guy. So what if the dated Framework Focus logo was stitched right above the front pocket. I hate it when people are late, so I chose to sacrifice fashion for promptitude. I snapped off my nametag, popped a couple TicTacs, and left the comfortable domain of retail computer sales and hopped aboard the first train in the direction of amorous possibility.

I was greeted at the entrance of Riviera by a man in a very nice suit who opened the door with a huff of indignation as I attempted to stretch out the wrinkles in my shirt as I hurried inside. I quickly glanced around the dining room and had a flashback to every first day of school ever, when all the kids were excited to show off their meticulously selected outfits, the new “them” for a new year, and I would timidly hunch over my desk in my brother’s oversized hand me downs, hoping no one would notice my shirts were intended for a kid 4 inches taller and 30 pounds heavier than I was.

Our table was at the center of the dining room, and when I saw Amy sitting there looking down at her menu, I closed my eyes and inhaled slowly, feeling that pubescent sense of dread and uncertainty fill my stomach, my mind racing to come up with the perfect introduction. She sat upright with perfect posture, her dark hair resting on her shoulders. As I got closer I realized that she was not just attractive, but easily one of the most beautiful women I had ever seen. It felt wrong for me to even be this close to her. You son of a bitch, Chris, I cursed silently. It crossed my mind that maybe parenthood had jaded Chris into a state of delirium in which he believed that there was a real chance that this would end in anything other than an awkward, humiliating rejection for me.

“Hello?” Amy looked up at me warily, with the expression of someone who ordered steak and was served jello instead. “Are you Charlie?”

I felt the sweat dripping down my back and I wondered how long I had been standing there without speaking. “Yes, Hi. Amy?” I managed to mutter while looking at my sneakers.

Amy shifted in her seat and smiled cautiously at me. “Would you like to sit down?”

“Yeah.” I mumbled as we made eye contact for a brief second. “Sure I would.”

I sat in my seat and looked at the woman at the table next to us. She looked to be middle aged and bored with her chicken as she glanced at me curiously, probably asking herself, Rich or escort?

“So Chris says you’ve known each other since you were kids? What was he like back then?”

My heart began to slow a little, realizing that Chris wouldn’t intentionally send me here to be humiliated. She was kind.

“He was pretty much exactly the way he is now, married and everything.” I laughed, and she reciprocated cordially. “So you just started at the hospital? I asked.

Amy nodded and smiled warmly. I could tell that this was a speech she had gotten used to giving. “Yes, I just began my fellowship last month. After I got back from Africa I took some time for myself but I’m ready to get back to the grind now.”

That pit of dread and uncertainty returned. “Fellowship? Oh, you’re like a doctor?”

“Yes.” she nodded. “Oncology.” I sighed and looked down at the table. “That’s really impressive.”

“It was mostly just years of memorization and all of my parents’ money, but thanks. Chris said you work at Framework Focus?”

“You knew that?” She really was a kind person. I began to answer when our waiter approached our table. He was an older man, his face neutral and non-judgemental and I wondered what it was like to spend your life serving dinner to strangers and relying on their generosity for your livelihood. The food you ate and the roof over your head depended on whether a person rounded up on a bill. Work is work, I know, but things like that take something out of you.

“Good evening, my name is Stephen and I’ll be taking care of you. Have you decided on a wine?

“A wine?” I asked sheepishly. I had only ever had sips of Rob’s dry IPAs back in college. I did not know anything about wine.

“What would you like, Charlie?” Amy asked. “You can choose.”

“Umm, well.” I stuttered, glancing back and forth between Amy and the waiter, “I think I’m in the mood for something cold?”

Amy tilted her head and opened her mouth to speak and paused, as if looking for clarification and I stared straight ahead, hoping that “cold” was an acceptable answer. Stephen broke the ice with a nervous laugh, smiling in Amy’s direction like I had told the best joke he’d heard all week.

“I think I know exactly what you mean, sir. I’ll return momentarily.”

Not much was said in the time it took Stephen to return with the wine. Amy asked about my commute, if I had trouble finding Riviera. I told her I was used to the wonky train schedule, and she thanked me for choosing a place so close to the hospital because it gave her time to change and get ready. Chris must have told her this was my idea. He’s good for things like that.

Stephen poured the wine for us. It was slightly opaque, and my heart fluttered when I realized that wine is expensive. Would it be too old fashioned to offer to pay? Was I supposed to ask to split? I put the glass up to my nose and muttered something about the scent taking me back to when I was 6 and mixing Kool-Aid with my mom.

“Have you selected your entrees yet?”

Dinner was what I expected it to be. Exquisitely cooked salmon and asparagus. Amy had lamb with pickled red onion and cabbage. We politely swapped stories but it was clear we were two people in two different places headed in opposite directions. For every story she had of her time in the Peace Corps, all I could think about was my time at Framework Focus. When she was inoculating developing nations, I was trying to convince elderly customers that they didn’t need a $2000 computer to email their grandchildren. She told me about the struggles of making sure her mosquito nets remained intact so she didn’t contract malaria. I spoke of the struggles of not having central AC in my parents’ basement.

There was a moment when Amy sighed and spun a piece of cabbage around her plate when I decided that there was only one way out for us. No, we weren’t falling in love and this was a terrible date, but it didn’t have to be a terrible night. Sometimes you have to admit defeat. You can’t win every battle. The white flag exists for moments like these and I was ready to wave mine.

“So right now you’re probably thinking that Chris has to be the greatest wingman in the world, right? Even I’m wondering how he sold this to you.”

Amy flashed her polite smile again, not yet ready to accept my concession. “He said you spent a lot of time in the theater district and the seaport, and that you would be a great tour guide for the museums there.”

I nodded, amused and appreciative at Chris’ attempt to make me sound more cultured than I am. “The tour guides at the museums are great tour guides. I’m just a guy with a discounted library pass.”

“You seem like you’d be a cool guide though.” Amy shrugged. She sat back and stiffened her shoulders.

“It’s fine, really.” I said. “Chris thinks a lot of his friends. We love him for it. Sometimes he sets his sights a little too high, though.”


I leaned forward in my chair. “Honestly, this isn’t pity talk or anything. It’s just straight facts. But you know what, we could just agree that I am completely out of your league. That would technically be true, wouldn’t it?”

Amy laughed. Her shoulders relaxed and she leaned forward. It was the closest we had been to each other all night. There it was. Concession.

“It hasn’t been that bad, you know.” She said as she took the last bite of lamb.

“My shirt has the name of my employer on it and I ordered ‘cold’ wine.”

She laughed again. “I honestly don’t know much about wine either. I was totally tossing that responsibility on to you. And you know what? I think it actually did smell a little bit like Kool-Aid!”

You never know what will bond you with another person. Real connection is fleeting and fragile, but sometimes all it takes is a shared moment, an inside joke, or a vague memory of what a children’s drink smelled like twenty years ago. Amy and I talked a lot that night. She told me about her insecurities as a new doctor and everything that was expected of her at the hospital. I told her that I needed to start wearing long sleeve shirts. We swapped stories and shared hopes and dreams the way only strangers can, like two travelers stuck in a storm seeking shelter for the night. We spoke intimately as strangers because we conceded that there was nothing more to be that night at Riviera. We spoke until the lights dimmed and we looked up to see Stephen gesture to the door where the well dressed man watched in a dazed stupor that I had made it this far.

If this were a romantic story I would say that Amy and I learned that night that opposites attract, that we brought out the best in each other. I would say that we went home together that night and that we’re still together today. But this isn’t that kind of story and I never saw her again. Sometimes, though, there are small victories to be savored in defeat. There are monuments erected for those who fought and those who fell. These monuments remind us to never forget. Now when I pass by the stone walkway of Riviera, or when I hear people commenting on the aromas they detect from whatever pretentious overpriced wine they’re sampling, I’m reminded of Amy, and I think of the best bad date I’ve ever been on.
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