Chicago Dating Photo: Ryan McGuire

I Hate When I See “Single” and It Refers to His Song, Not His Availability

We are as he called it, “grandma dancing” in the club to Snoop Dogg. I think this might be one of my favorite moments.

Meeting at a 4 a.m. Bar

It was 1:40 a.m. It was a Friday night, and I had woken up an hour ago.

“When did you want to meet?,” I texted.

“Now,” he said.

“Okay,” I texted, slipping out of my pajamas.

I grabbed my lipstick and turned on the bathroom light.

My phone rang.

“Oh, he cannot be there already,” I thought.

I looked down at my phone and answered, “Hey, I am going on a date. I literally slept through my entire Friday night.”

“So now you can tell him you woke up like this,” my friend laughed.

“Yeah, no. I am getting ready, but—he just texted that he is already there.”

I continued the conversation with my friend as I hoped on the train into an empty car.

“Hey, my phone is dying. I am upstairs,” my date texts.

“Okay, I am almost there.” I reply.

The night was full of energy. It feels  like 10 in the morning, but it is really closer to 2 a.m. and all of the bars are letting out. I passed the double date under the Wrigley Stadium sign. The girl in the white dress was done with her shoes. She slipped them off and continued to smile and lean on her date.

I crossed Clark street and merged with the crowd. One girl in a floral, summer mini-dress high-fives all of the buzzed men who pass her.

The last guy to receive her high-five is still smiling as he passes by me.

Finding Your Date in the Club:

I arrive to the one bar opened past 2 a.m. A group of friends introduces newcomers, as a girl in a backless summer dress signals taxis to keep going as she waits for her Uber.

“I am in, where are you?,” I text, moving through the upstairs crowd.

“I am downstairs,” he says.

“Oh, I am upstairs. Coming.” I texted.

Two minutes late I travel from upstairs to downstairs. I search through the crowd and nothing.

My phone pings.

“I will meet you,” he texted.

A line started to form to go upstairs. The bouncer was making us wait for access.

I made it upstairs and approached the bar.

I wryly smiled at a guy and then turn around. I don’t think that was him.

The bar was lightly packed. There were enough people, but it wasn’t overly crowded. I made my way to the exit sign and asked him to meet me there.

I look around and see people stumble and laugh from their shots and filtered beer.

I make my way through the crowd, ready to leave. It’s been about 5 minutes of silence. While I was interested to meet this guy, I was content with going home.

As I shuffled through the crowd, a man stopped me and said, “Amanda?”

Dance With Me:

“Hi, how are you?,” he asked, Budweiser in hand. We moved to the ledge of the bar.

“What are you drinking?,” he continued.

I wasn’t drinking anything at the moment, but I answered, “water.”

He motioned the bar tender to grab me a cup of water.

“You’re cute,” he blurted out.

I couldn’t tell at that moment if I liked him. I smiled back.

“But, you’re in a sweater and it’s 80 degrees outside,” he commented.

“It’s a summer sweater,” I said. “I am trying something new.”

I sipped my drink, and he put his hand on the small of my back trying to get closer.

“Oh, that’s nice,” he smiled, liking that my sweater opened up in the back.

I turned my attention to the TV. They were playing old school 90 and 2000 music. “SheWolf” was currently playing and then it changed to 112, “Dance with Me.” I missed the beats of the 90s and sway my body.

“What do you know about 112?,” he smiled, grabbing my hands.

“I am the best at grandma dancing,” he said as he spun me around. Are bodies synced to the rhythm and my face met his.

The Other Guy:

“It looks like he went to Lolla, too,” I pointed to a guy, who was standing next to my date.

“Hey, man, did you go to Lolla?,” he asked. My date was so outgoing.

“No, I didn’t have the chance,” he said engaging in conversation. He ordered a drink. The bartender came back with a few shots of Tequila.

“I lost my best friend tonight,” the new guy said.

I interjected, “Like lost as in dead or no longer friends?”

He swiped his pointer finger across his throat.

“Sorry, man,” my date said.

“Come on man, take a shot with me,” he motioned to his group of friends on the dance floor.

I turned to my date, “That’s so sad.”

“Yeah, but I didn’t know him. It’s a sad thing, but we can’t let it bring us down,” he comforted me and turned my attention to the next song.

Snoop Dogg:

The guy we were talking to started dancing with the birthday princess as a circle formed around them.

It was Snoop Dogg, “Drop it Like it’s Hot.”

“Are you going to drop it like it’s hot?” he teased.

“No, I don’t know how,” I lied.

Then, he did it. He literally, just brought his elbows out and made fists with his hands and dropped it. Again and again.

I silently chuckled as he enticed me to join him. I turned my head and he grabbed my hand.

There we were grandma dancing to “If the pimps in the crib, ma, drop it like it’s hot.”

It was last call and we headed down the stairs out into the summer night.

Late Night Conversations on the Red Line:

He walked me to the train station.

We sat down and then my date started talking to the guy in the corner.

“You went to the Witt, tonight?” my date asked, noticing his wristband.

“Yeah, it was great.”

“Free food?” my date smiled.

“Yup, free food.”

They both got really excited about free things.

“I just came from Paris and was getting free drinks all night,” the guy went on.

“Awesome,” my date smiled.

He was a DJ and started rattling off all the bars he went to.

“Oh, you’re a DJ?,” I perked up, “I am reading a book about DJ culture,” I said and reached for my purse.

“Wait, you have a book…in your purse,” he said confused.

“She has a book in her purse, dude,” he looked up at my date.

“I didn’t know she had a book,” he said.

“Well, yeah, I didn’t know what to expect from this guy, so I just brought a book.”

“She never brought it out, bro,” he said.

The doors opened for the next stop and the DJ got up and wished us well.

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