1983
New York City, New York
"What? You spent a night in jail?"
"Yes." Conan smirked. "It's a long story."
Conan was back in New York, he called June beforehand to tell her he was coming by. The weather was pretty nice, he decided to see her during spring break. He took the train and arrived by the end of the afternoon. They stopped at for hot cocoa again, but decided to take a walk and talk for a bit.
As usual, and as everybody knew, Conan enjoyed pranks. Not simple pranks either – like scares or pie on the face kind of pranks. His Lampoon friends weren't different, and they tried to make the most out of them. They pissed pretty much everybody off, even some students weren't amused by it, especially the Harvard Crimson writers. Conan was caught and jailed for wasting everybody's time, but as he told June what happened, and he saw the smile on her face, he knew it was worth all the trouble.
Conan and his friends decided to trick the Boston police by posing as construction workers, with uniforms and tools. They went to downtown Boston and started jack hamming the pavement. As silly as he could be, Conan phoned the Boston police reporting the crime: some college students with hats and construction gear started destroying the pavement, and they should be stopped... soon.
He then phoned the Massachusetts state police, to report another crime: college students, dressed as police officers, were disrupting construction workers and they should also be stopped... quickly. They watched the police arriving to arrest... the other policemen. As hilarious as it was, law enforcement figured out who was the mastermind behind the "crime" and Conan was arrested. From the moment he was handcuffed and his rights were read, to the moment he was conducted to a police station and had to sleep behind bars, it was a surreal experience.
"Roxy didn't really care about it... or found it funny."
June shrugged. "Well Conan, it's pretty stupid, I have to be honest."
Conan smiled sadly at June.
"Don't be caught the next time." she said, and both laughed out loud.
-
"So you're leaving?"
"It's my last semester here."
Conan sighed, in frustration. "Are you... moving?"
Roxy already knew Conan wouldn't last with her. She didn't know at this point that dating him was good or bad, but she knew deep inside and in the long run, they weren't made for each other. This was not about marriage, or about having kids. It was just about a person she liked and admired very much, but that wasn't the right fit. Breaking the news like this wasn't the easiest thing to do.
"But what about us...?"
Roxy sighed. "I wish I could do this differently."
Conan looked puzzled. He was standing in front of his dorm, with his then girlfriend telling him she had to go. "Why..."
"We're not working out. I think we have different goals..." she smiled sadly.
"I'm gonna move out soon, and we won't work out far away. I hope you understand."
Conan nodded. "I'm doing this now because soon I won't... be here. And I don't think that just disappearing and not answering calls would be fair to you."
"This is not fair, Roxanne." Conan said.
Roxy wanted to be honest. One of the reasons this relationship wasn't working out was because maybe Conan was too young and she was probably his first girlfriend, and maybe he didn't know how to deal with it. He wasn't unfaithful, he was really respectful, but something was missing. He wasn't completely present. He devoted a lot of time to... June. Roxy never thought he would meet June to cheat, he never lied, he always told her he was with his best friend.
Roxy only realized, after that picture on his nightstand, and observing the way he acted when he talked about June and the amount of time that he spent with her, that he was probably in love. She didn't feel used, or betrayed, but his heart was in the wrong place. She wouldn't ask him to drop June from his life, they were really close and it would ruin a friendship for a very short lived romance. However, Roxy felt more comfortable just breaking up and going separate ways, as friendly as she could do it.
"It's not... but it has to be done."
Conan closed his eyes and shook his head in denial.
"Farewell, Conan." Roxy said, teary. "I wish you the best."
Conan would think about Roxy for the next several weeks. They were together for seven months, seven intense months. He would see her around, and she would avoid him as much as possible. He would then glance at her from afar, until the day she just disappeared. He would walk around the corridors, hoping he would see her again... but no. He wasn't devastated, or broken, but he missed her presence. As the weeks went on, he did realize Roxy was probably right – they weren't made for each other. He remembered her fondly, and he didn't hold anything against her.
She had been great, supportive. Conan still remembered her voice, and her smell and he understood that at the end of the day, it's best to break up amicably than fighting and breaking each other's hearts, and that sour taste that lingers for months. Conan at the age of twenty had been through his first breakup, and as disappointed as he was, he grew past it and learned with it. Not everything has a happy ending. People are unpredictable, situations change, and feelings change. He was okay with that.
