Valentine’s Day has always been lackluster for me, until I became single.

This is a Chi-town story. Maria was a film school friend of mine who had begun coordinating a concert for some Puerto Rican guy I had never heard of. She advertised via Facebook that she was in Chicago, so I sent her a message requesting a meetup. She said that she was only in town for the night of the show and invited me out.

A Puerto Rican concert on Valentine’s Day was beyond bizarre to me.

The stage was built in a way that made it rotate, completely changing the scenery with each quarter, and the giant LCD screen above produced LSD-like images as all the hispanic girls went crazy for the Puerto Rican George Michael. I asked Maria what was going on and she could only laugh in response. That’s when my senorita popped up on the stage in a red dress that bloomed at the bottom. Violin in hand she played a melody I didn’t need Spanish classes to understand. After the concert was over I accompanied Maria to the hotel where the backstage crew was planning on hitting a bar down the street.

We awaited in the lobby and I saw my lovely red vixen standing near the doors, talking to the slick guitar player. Maria noticed my noticing. “You like her?”

“Sure. What’s not to like?”

“Why don’t you go up and talk to her?”

“Are you kidding?” I scoffed, “She’s clearly with that dude.”

“That guy? No. That guy’s married with two kids.”



A Spanish violinist on Valentine’s Day. Luck be a lady. I gathered myself and walked up to her with swagger I didn’t know I possessed. “Excuse me.” She turned and smiled at me underneath her dark brown eyes. “I thought you were really great up there. I only caught the tail end of it. My friend’s the coordinator.” I pointed to Maria for reference.

“Oh thank you. That means a lot!” She perked up. The guitar man looked a tad jealous, but given the new info I had obtained I ignored him. A backup singer joined the posse just as Maria’s friends were getting ready to head out.

“So I think we’re gonna go to this Irish pub that’s like a block away. You guys wanna come along?” The senorita turned to her friends like a child asking her parents for permission. The backup singer posed a problem.

“No, we have to get up early in the morning.” My lady looked disappointed.

“Well it’s only a drink or two.”

“Yeah, that sounds fun!” She chimed in for her friends.  “We can meet you guys there in a bit.” This was too good to be true. I tipped my invisible hat to the talent and we went off on our own. As we got closer to the bar I began to hear music. Something was off, though. It was different. It was karaoke!

Oh boy!

Everything was falling right into my lap. I already thought of a great song to try to serenade my mystery woman. Bruce Springsteen loved himself Spanish ladies, and in a conversation with Carlos, I found that I too shared the same affinity. Rosalita was a perfect song for the occasion, and it was my favorite song to sing. Maria agreed to purchase my drinks for me, seeing as I spent nearly two hours on the transit getting to her. I immediately put my name in the hat and we took a seat big enough for the latecomers. Midway through the first drink they walked in. I didn’t even have time to contemplate them not coming. We waved them over and engaged in conversation, mostly about their touring.

Rosalita and I seemed to be hitting it off pretty well, and she said they had been on tour for most of the year and weren’t even halfway done yet. The backup singer only got more annoying as she kept pleading with everyone to leave. I pulled out my oncoming song as a reason to stay. Rosalita’s eyes lit up. She wanted to hear me sing. I pointed at the TV list that showed I was coming soon. She agreed to stay.

That’s when things took a turn.

I ran up to the stage and snatched the microphone from the stand. Right when those first lyrics came up on the screen, Rosalita and her posse stepped outside. I was already up there, however, and I was in fact singing my favorite song, so I let myself go as if nothing had happened. Halfway through Rosalita stepped back inside and watched me momentarily. When we caught eyes she waved and went up to Maria’s table for a quick word, then walked right out of my life. I was disappointed. When I came back down Maria told me that she said to say goodbye and that she thought I was good.

“Also,” She began with an uh-oh tone in her voice, “apparently I was wrong. She was with that guitar guy.”


“Yeah. He’s divorced with two kids.”

And I looked like a total dick hitting on her right in front of him. Oh well. I’d never see them again. Instantly I scanned the bar for another lonely heart. Maria got me another whiskey rocks and my eyes shifted focus from red to black. Through the crowded bar I saw a woman capable of being Krysten Ritter in a black dress fit for a fancy dinner. She had what looked to be chocolate milk in a martini glass and was equally scanning the bar. Her eyes settled on mine and she smiled. I returned the kind gesture and raised my glass. We air-cheered and she sat at the table. “I’ll be right back.” I said to Maria, standing and approaching what could be my second celebrity of the evening.

“Hi.” Her head cocked in my direction and she smiled coyly with her chin resting on her bare shoulder.


“I’m Errol.”

“Vivian.” She invited me to take a seat and I accepted. We talked for the rest of the evening about various things from Valentine’s Day being an insult to singles to the upcoming Fleetwood Mac concert. She bought me another drink and by the end of the night we may as well had been best friends, aside from her real one who was sitting on the other side of her in the same kind of dress. The bar was getting ready to close and Maria came up to say her goodbyes, with a follow up text informing me of access to a separate hotel room if it were necessary. Vivian stood up and threw her jacket on. “We were gonna head to this 4 AM bar called the Exit. Ever heard of it?”

“No, what’s that?”

“Oh it’s awesome! I used to bartend there. They play porn on the TV’s. It’s like a punk rock bar.”

“Sounds great! Let’s do it!” Then she put her hand on my shoulder.

“I have to be honest though…I have a boyfriend.”

Snuffbox flooded my mind.

Really? We must have been talking for like two or three hours here! On Valentine’s Day! And you’re gonna drop the boyfriend bit on me now!? After everyone’s gone! What the fuck! Fuck you! Fuck you Fuck you Fuck you Fuck you Fuck you Fuck you Fuck you Fuck you Fuck you Fuck you Fuck you Fuck you Fuck you Fuck you Fuck you.

“I still really want you to come though.”

“Sure.” I said. She smiled a little too widely.

“Great! I mean just cause I have a boyfriend doesn’t mean we can’t hang out.”

“Yeah.” I said, gulping down the last half of my drink. Vivian ordered a cab and I climbed in the back with them. At least this bar was much closer to my apartment with Rob. Vivian’s friend became hysterical in the cab ride. Apparently her boyfriend broke up with her and she was upset about it. “Why’d he leave me!” She shouted in anger. She literally grabbed my by the collar and pulled me in. “Why!?” I put my hands up in defense.

“I don’t know!” Vivian pulled us apart.

“Stay back.” She said, “Oh baby come on. You’re too good for him and you know that. He’s a piece of shit.”

“I know.” She sniffled, “I love you.”

“I love you, too.” They pecked. Then they kissed. Then they made out, right in front of me.

That’s cheating, right? That counts? She’s a cheater, then.

We arrived at the bar, and before paying the cabby Vivian took a very classy piss right next to a car outside as people walked by. I turned around and she complimented my gentleman-like action. We walked inside and holy shit this place was packed. There was a stripper pole in the middle of the dance floor and Vivian ordered all three of us a beer before taking it on. I shook my head as I took a seat and drank my beer. Her and her friend danced as two poor souls came up to try to get with them. Vivian grinded on one, shoving him against the wall and her friend stumbled her way over to me, tripping and falling into my lap. “You all right?” I shouted.

She nodded and Vivian came by to collect her. “We’ll be right back.” She said, before taking her away.

I never saw them again. They didn’t come back for their beers, and I texted her saying bye before deleting her number. I inched my way to the exit and another young lady looked at me and smiled. I winked at her.

“Wow!” she said, “That’s a great wink!”

“Why thank you, I worked very hard on it. It’s difficult to make a wink look classy.”

“Yeah, yours is great!” Some dude approached.

“What’s goin’ on?”

“You should see this guy’s wink!” He looked at me, and I winked at him.

“Whoa, that’s great!” He said. He then grabbed my shoulder and spun me around, “Why don’t you go try it on some other girls?”

Fuckin’ dipshit.

I left that bar defeated, beaten, battered and dreams shattered. I got home at 3:30 and crawled into bed, laughing about all the faux possibilities of the evening. It’s safe to say I’d never had a more promising night before or since. The peak of which was my Rosalita moment. For that reason, the song itself pulls the February ’13 memories to the forefront, and I laugh to myself in a room of people who probably question my sanity.

I started drinking when I became single. I hope I stop when/if I end up in a relationship again. I’ll still go out, of course. Years down the line at a bar and in the arms of a new beloved I’ll ask her if she’s ever heard Rosalita before. She’ll shake her head and I’ll excitedly run to the jukebox, pissing away money on a moment that could easily be part of pillow talk. The guitar will ring out and the Big Man’s saxophone will propel the song into full swing and on my dash back to the bar I’ll trip, because my balance will still suck. The corner of the bar will pierce my temple like an ear before I even get the chance to process where my head is headed. I’ll freak out the stranger sitting next to the bar with my sudden rag doll-like behavior. The saddest part: the song that caused it all will cut from the jukebox in the panic. My days will be over and I’ll drift peacefully into my sitcom style memories and die thinking of the worst Valentine’s Day with the best opportunities a man can ask for.

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