A Love Story

Jake and Caroline had been dating two-and-a-half years. They were introduced by Caroline’s best friend, Ronnie, who had met Jake on Tinder. After four weeks of drunken hookups that left her unsatisfied and him horribly embarrassed, Ronnie thought Jake would be perfect for Caroline, who was still recovering from a devastating break up.

Ronnie knew her best friend well and was sure that the thing Caroline needed to get her over the heartbreak hump was a quick roll in the hay with a handsome, mostly charming and funny guy like Jake. She was confident that because he was so bad in the sack, there was no way Caroline would fall for him and wind up in yet another relationship, which was her mo. Ronnie knew that the best thing she could do for her friend was help her break the cycle of disappointment.

Jake and Caroline’s first date was at The Whistler. They talked about Ronnie, how much they loved The Walking Dead and debated the better ride-share service, Uber or Lyft. She was Uber, he was Lyft. They got wasted on Sazeracs and had sex at her apartment. It was incredible for both of them. Caroline stopped taking sex advice from Ronnie.

They quickly grew close during their Sunday night Walking Dead viewings, dinner dates and in-depth talks about their past relationships, families and wounded hearts. They fell in love. Ronnie, who was still scouring Tinder for love of her own, became jealous and had a falling out with Caroline. But Caroline didn’t care. She had Jake, and Jake had her, and that was all that mattered.

So when Jake proposed to Caroline on the roof of the newly opened Robey hotel in Wicker Park, all of the other friends were not surprised and were happy for the couple.

"We’ll be the great love story. Greater even than Romeo and Juliet.”

It was a chilly Saturday night in March. The outside of the rooftop was closed because of the rain but Jake had made prior arrangements. Caroline had no idea what she was in for when the Robey’s rooftop hostess escorted them past the bar patrons and outside. Jake did his best to disguise his nervousness by discussing Chicago’s grid structure as they looked out on their city from thirteen stories high.

“But then there’s Milwaukee and Ogden and Elston,” Jake said.

“They screw everything up,” Caroline said.

“Exactly,” Jake said smiling. He was more certain than ever in that moment that Caroline was the one for him. A tattooed bartender walked out and handed the young couple two Sazeracs.

“This is our special drink,” Caroline said curiously.

They clinked glasses and took a sip. Jake took the glass from Caroline’s hand and set both drinks on the edge. He reached into his inside jacket breast pocket and revealed a black ring box. He took Caroline’s hand and a knee.

“Caroline Michelle Winters,” he began, “I loved you from the first Sazerac we ever had and I’ll love you until the last. You have brought me such perfect joy that I don’t ever want to feel anything less. I know that with you by my side, your hand in mine, I never will. And so, Caroline, love of my life, will you marry me?”

She was crying. The tears ran down her face like a mad flood over a smooth, Midwestern plain. “Yes! Yes! Of course, yes!”

The patrons inside had been watching it all go down and cheered when they kissed.

“I’m so happy,” Caroline whispered. The tears on her lips, mist against his ear. “Let’s stay this happy forever.”

“I’m glad you said that,” Jake said. “I want you to do something with me.”


“I meant what I said. I don’t want to ever feel anything less than the perfect joy I have felt, and feel right now.”

“Me, too.”

“Let’s die together.”


“Right now.”


“Let’s throw ourselves off of this rooftop. I’ve done the research. Thirteen floors up will definitely kill us.”

“Are you insane?”

“Think about it. We’ll preserve our love—perfect—forever. We’ll be the great love story. Greater even than Romeo and Juliet.”

Caroline looked deep into the eyes of the man she loved more than anyone or anything. She pulled away from him. Just enough to reach the two glasses of Sazerac. She handed one to Jake. She smiled at him. They took a sip. They both smiled. They laughed. They slugged back the remainder of their drinks. She took his hand. He helped her climb on to the edge where the Sazeracs had safely stood a moment ago. The bar inside expressed confusion. The tattooed bartender made a dash to the door and just as she pushed it open Jake and Caroline stepped off the edge and took the plunge.

The impact made a mess of their bodies but their fingers remained interlocked despite being partly mashed into Milwaukee Avenue. Traffic was a nightmare through early Sunday evening as authorities investigated and cleaning crews removed the remains.


An easy way to fill someone’s heart with warmth and their eyes with tears is to tell them a story about an old married couple that died together in their sleep. It was the entire point of The Notebook. Another way to yank at someone’s heartstrings is to have one of the old people in the story die with the remaining spouse pass away hours, days, weeks or months later, the way Johnny Cash followed June Carter four months on.

Yeah, people love those stories. Me, too. What’s not to love? Ah… romance.

We don’t hear enough about young couples who die together in romantic, grand ways. It’s unnatural. Young people don’t die together in their sleep unless there’s a carbon monoxide leak or they’re murdered. For death to be romantic, the couple needs time to live. But why not stop when you’re ahead. Jake and Caroline ensured their perfect love would remain that way. They would not let time tarnish their gleaming smiles or shave away the patience and comfort and trust they had for one another.

But this didn’t really happen. The couple I saw get engaged on the roof of the Robey came back in to those cheers and will likely go on to have a perfectly ordinary, hopefully mostly joyful life together.

Ah… how boring.

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