Fifteen First Dates

What would the literary greats have had to say about the world of dating today? Would Jane Austen have made a Tinder? Would Robert Frost make midnight booty-calls? Would Oscar Wilde have casually dated four girls, then end up ghosting any who had the audacity to ask ‘what are we?’

It had been two long years since I was last romantically involved. I had decided to take a break from men after my ex-boyfriend of four years woke up one day and had an epiphany that it wasn’t his time to be tied down, that he needed to focus on pursuing his dreams of being a content creator.

Having planned the rest of my life with someone and then getting the rug ripped out from under me took its toll. I went through all five stages of breakup: not accepting we were over, burning all the things he ever gave me in a dumpster fire, promising to be a better partner and begging for him back, bingeing on ice cream and Netflix, then finally throwing myself into my work. As I was in no rush to get back out into the millennial dating world, the last stage lasted for the past year and a half up until present day, when a couple of my girlfriends and I got together for a brunch.

“Heyyy baaabe! Oh my god, it’s been forever. You look so good though, have you been working out?” Vanessa was a tiny package that packed a big punch. What she lacked for in height, she made up for in personality and a mane of luscious long brown hair. People either hated her, or loved her, no in-between.

“Hmm, well I suppose it could be what started off as the depression diet, but then eventually evolved into the ‘seven-coffees and eleven-hour-days’ fast,” I said with a wink.

“Aww, babe no!” She puffed out her bottom lip and reached out to squish me into a tight hug. She then held me out at arm’s length, looked into my eyes and said, “at least you look hot.” God, I love her.

“F-ck that! No man deserves that much energy from you,” snapped Sandra. “But she’s right, you do look good,” to which we all laughed. Sandra was more mature and grounded than me and Vanessa and our obnoxious antics. She had the warmest heart but wasn’t afraid to give you the judgmental side-eye if necessary.

“Listen, trust me when I say, I am over being sad about it. I have accepted my fate. All that negative energy has been transferred into putting in extra hours at work, focusing on ‘doing me,’ and excelling in my career. I see nothing wrong with that.”

“And we are so happy to hear that,” said Vanessa glancing over at Sandra, “because we have a proposition.” Their eyes widened as their mouths twisted up into smiles, giving off twins from The Shining vibes.

“What,” I said with a sigh.

“We want to make you a Bumble!”

“You’re joking,” I said flatly.

“Bitch, no! This is not a joke. It’s been two freaking years of you, yourself, and more you, and it’s time to get back out there,” said Sandra.

“Yeah, and besides, you’re probably all rusty, dusty, and crusty now,” Vanessa said eyeing me up and down. God, I hate her.

After taking our orders, and much convincing, the girls persuaded me to hand over my phone so they could create an account for me. They picked out my pictures, wrote up my bio, and set up my search parameters so that all I had to do was swipe.

Halfway through our first round of mimosas, I finally looked up from my phone and said “is this really the best Miami has to offer?”

“Oh, come on, you’re hardly giving it a fair shot! You’re judging these guys off a handful of pictures and 50-character bios,” said Vanessa.

“Well if that is all they’re given, you would think they’d make a better attempt at selling themselves!”

“And to answer your question, no. That is not the best Miami has to offer…you won’t find the best anywhere has to offer swiping through Bumble,” said Sandra. “This is just to get you started.”

“Yeeaah,” said Vanessa who was now swaying back and forth waving her hands around in support.

“Putting yourself back in the gaaaame,” said Sandra, now also following Vanessa’s swaying. They looked so ridiculous that I couldn’t help but let out a laugh.

“Fine, fine. I’ll lower my standards. Just for you girls,” I said rolling my eyes.

“That’s all we’re asking,” cooed Vanessa.

Three hours, six dishes, and nine mimosas later, I had a total of fifteen dates lined up. I had no idea how I had reached that amount, but with that much hype from your girls and a little help from alcohol, the candidates did seem to have more appeal.

The plan was simple, every night for the next two weeks, I would go on a date. Two on next Saturday! A close friend of Vanessa’s who I’d met at a few parties was a bartender at La Mar, one of Brickell’s hottest restaurants overlooking the Miami skyline. Vanessa persuaded him to hook me up with free alcohol. When he heard I was finally dating again, he was more than happy to oblige.

Back at my apartment, over a fresh box of Krispy Kremes, the three of us planned out my outfits, hair, and makeup looks for the next two weeks. I may not have been all that thrilled in the beginning, but it sure as hell was starting to get fun.

Monday rolled along and I had my first date at 8:00 PM. I had insisted on meeting him there so I wouldn’t rely on him for a ride in case I needed to break away. I was dressed to kill, a black satin dress that hugged my curves but draped in all the right places, and black heels with an ankle strap I had borrowed from Sandra. It was my first night back on the dating scene and I was determined to look the part.

My date’s name was Jose. He was a year younger than me, a starving architect with a love for Disney and dogs. His hook nose was a little distracting, but he had a good sense of humor and perfect teeth.

“Can I get you any drinks to start?” asked the waiter.

“I’ll have the Merlot, please.”

“And I’ll have the Naked & Famous in Lima,” he looked at me over the menu and wriggled his eyebrows. Christ.

“So, Jose,” I started after the waiter had walked away, “what are some things you do when you’re not designing amazing houses on star island?”

“I try to work out every day. I used to be pretty big as a kid so I definitely prioritize going to the gym after work.” Healthy lifestyle habits, I thought. Very nice. “But honestly, I love getting drunk with my boys and shooting the shit around Brickell or Wynwood. Have you ever been to El Patio or Shots? Those places are so ratchet, but hella lit.”

“Once or twice a few years back,” I muttered as the waiter approached with our drinks. I gulped down my Merlot and immediately asked for another. Thank god my drinks were free.

Tuesday came, and I hoped it would be more promising. Statistically, it was impossible for me to have hit it off with the first guy, so I didn’t let it discourage me. That night I wore white skinny jeans, a chiffon burgundy camisole (sans bra), brown cork wedges, and gold statement earrings. Different look, still killed it.

Date number two was a computer engineer named Mitch. He had tight kinky curls, wire glasses, and an ambiguous skin tone leading one to believe he was Hispanic, Polynesian, or half-African American. He was a little underdressed for La Mar, but he had the laid-back IT Silicon Valley look which I didn’t mind anyway. When the waiter asked for our drink order, we both got the Merlot.

“Two computer geeks out on the town,” he chuckled to himself. “This view is unreal, you picked a nice place.”

“Thanks, I’d been here before and loved the scenery so I figured I could share it.”

“I can’t say I love Miami though, I’m way more a west coast kind of guy. But I came back to help my mom with a few things so I’m working from an AirBnb in Ft. Lauderdale which isn’t too bad.”

“Aw, that’s so sweet of you!” Good relationship with his mother, I thought. Very nice. “Such a thoughtful son.”

“Oh, speaking of, are you into plants? Like, house plants?”

Odd transition, but okay. “Yes actually! My goal is to cover every open spot in my apartment with plants so I’m in some sort of makeshift jungle,” to which we laughed.

“I’m doing this thing where I go around cutting off pieces of plants from outside and propagating them until they grow roots so I can plant them in a pot. I can grab you some if you’d like.”

“You mean like, you steal public plants?”

“Well, they’re outside so they don’t belong to anyone. Technically it’s not stealing.”

“Right, yeah. Interesting.”

The more he said, the faster he started talking, and jumping from topic to topic. He clearly had severe ADHD and his left eye was starting to squint a little more than his right so in truth he looked a bit crazed. The waiter came with our Merlots. I drank mine down and asked for a second.

Dates three through fourteen shockingly all started and ended in the same way. I walked in with confidence, dressed to the nines, had a list of positives about the man sitting in front of me, and had a breathtaking skyline lighting up the night. Then before my Merlot would even make it to the table, some glimpse of the impending bomb would rear its ugly head, and I knew I would never meet with these men ever again.

Sunday evening number two, on my fifteenth and final date, I was physically, mentally, and emotionally exhausted. How the hell had I met with fourteen man-children and not have felt anything for any of them? Was it me? Was I jaded to the point of no return? Had I become some shriveled old heartless hag with overly high expectations? Should I change my own perspectives and lower my standards to accept men that still get sloppy drunk at twenty-nine, or steal public plants and have a wonky eye, or take steroids for gains, or practice polyamory, or openly discuss their past relationship drama leading to tears on the first date? Am I just being picky?

Mentally scrolling through the rolodex of my experiences from the past two weeks, I got a text from date number fifteen. He canceled. Ten minutes after we were supposed to meet. A fitting end to the previous two weeks.

I texted my group chat with Vanessa and Sandra breaking the news. They replied within seconds saying they’d get dressed and grab an Uber. In the meantime, I made my way to the bar, where I saw Vanessa’s friend, Pablo, mixing some drinks. I waved and he grinned as he started walking over to me.

“Hey Pablo, can I get a—”

“Merlot, I know. You’ve cost me a few bottles the past two weeks, I didn’t realize you could put that much away,” he chuckled.

“Sorry about that, it’s been a rough couple of dates,” I said shrugging.

“Yeah, I was witness to it. Those guys were lame as hell.”

“Tell me about it! I blame Vanessa,” we laughed.

“No free drinks for her then,” he walked away to serve the customer their mixed cocktail. When he came back, he brought my glass of Merlot with him. That night, I would finally be able to sip it slowly.