I just can't win. I thought I had something. I don't think I do yet. So I wrote this. TL;DR at the bottom. Alfa 8C for your time.
He took a seat on the worn and splintered park bench. When things went wrong, he'd escape here. Something about the serenity of the park after hours, away from the screaming children and drunken teenagers was really soothing. He sat with his hands supporting his face, a tear slowly forming in his right eye.
Another failed night. Another failed attempt at happiness. He had been following her for months now. They first met in his history class at the community college. She was beautiful. Her straight dirty blonde hair was always kept neatly out of her face. Her big deep blue eyes pierced everything, including his heart. When they first made eye contact, he felt a connection. He doubted it was mutual, but would spend months trying to find out.
He carved her name into the bench. In small letters right on the backrest, away from every other marking, the name 'Jenn' popped. He did this after she got her first boyfriend, who wasn't him. He blamed himself for this. "If only I moved faster. If only i could have more confidence. If only…" It was at this point he'd turn and punch the opposite side of the bench. It was the cause of his bloodied knuckles.
When that relationship fizzled out, he tried again. They began talking. He was loving the attention. It made him feel valued and important. But then, without any real warning, she moved on. Again, he was alone while she was in the arms of another man. He engraved her name deeper into the wood. This time, he underlined it. It was crooked due to the shakiness he had in hand. "Why can't I do anything right?" he cried. "What is wrong with me?" He curled up on the bench and broke into tears.
It was here that he dreamed about her. It was vividly detailed but fully accurate. The message on his phone explained a connection she had with him. She liked him. She wanted to spend time with him. A smile grew on his face; he tried to hide it but the joy was just too great. He got in the car and drove. She was outside her house, waiting. He opened the door and walked up to her. Her arms quickly wrapped around his neck and the words "Thank you" were whispered into his ear. As they walked to the car, he opened her door first and let her in. He then got in himself. He rested his hand the gear shifter, and pulled onto the road. Her hand quickly followed and was right on top of his. A smile grew on his face. He quickly looked over and saw that she too was wearing a similar smile. They drove and talked. For hours on end, they drove down empty roads where every light was green. Momentum never stopped.
He woke up abruptly when he felt water droplets hitting his stubble covered face. As he opened his eyes, a loud clap of thunder engulfed the silence. He jumped up quickly and ran towards his car. This time, it was empty. There was no smile. His hand was on the gear selector, alone. As he left the park, he was blinded by the headlights of oncoming traffic. The mood of the car was bitter. Laughter was nonexistent. All that could be heard was the subtle roar of the heater. This wasn't what he wanted.
The car was jerked over to the shoulder. His hazard lights pierced the otherwise dark road. He began messaging her.
"Hey! What's going on?" He typed. "Yeah, thats good. Small talk first." he told himself in his head.
She responded way faster than he ever expected, as if she was waiting for his message.
"Not much at all. Studying for some test I have coming up."
"Thats not fun at all." he replied.
"No. No no no. Its awful!" she typed back. He pictured her smiling at her own comment.
"Can I tell you something?" he nervously typed. He didn't hit send quite yet. The nerves were getting to him now. He was second guessing himself. His eyes shut and he pressed send. When she quickly gave him the "what's on your mind?" response, he knew he was too deep to go back. This was it. There was no getting out now.
"I… I like you, a lot." he was shaking now. His foot was violently tapping the dead pedal.
"I would love to spend some time with you outside of school." he finished. His heart was racing. This was not how it was supposed to happen. The plans of being there in person and doing an elaborate act were over.
The phone dinged. He was scared to read it. He closed his eyes and took a deep breath, scared to read what was typed back.
"I know you do! Haha" she replied.
"Shit!" he told himself. That was not the response he was looking for at all. "How the hell do I take that?" he questioned. He struggled to make a reply.
Outside the sky was somewhat clearing up. He swung a U-turn and headed back towards the park. Once in the parking lot, he decided what to send.
"Do I ever have a chance with someone like you?"
"Anythings possible." was the first message. This got him feeling good.
"But I'm kind of done with guys for a little while." she finished.
"FUCK!" He yelled to no one in particular. He smashed his hand into the steering wheel, the horn blaring for a good ten seconds. He went back out to the bench. He took up the familiar seat. This time, he drew a box around her name; these three new lines not perfect but less crooked than the underline.
He lifted his fist. He wanted to punch his traditional spot; the one where you can see the slight indentation in the wood. But he didn't. He opened his palm and held it to the sky. Water droplets hit it softy. He then held it over her name. He teared up again.
"It'll never happen." he told himself. "It'll never be."
TL;DR: My luck with girls sucks. I don't think I have any chance again.