First try.
Frank walked up to Charlene's house. He didn't really know what he was going to say but he knew he was going to have to break it off with her some how. When she opened the door she was wiping away tears, surprised to see Frank.

“Oh,” she said and cleared her face, “Hey, Frank.”
“What's wrong?” Frank asked.
“It's nothing, come in,” Charlene said and opened the door to allow him to come walk inside.
“Are you alright?” Frank questioned, concerned.
“No,” she said with a nervous giggle, “But I will be.”

Charlene guided Frank up to her bedroom and they sat on her bed.

“What happened?” Frank pestered, “Why were you crying?”
“Just these girls were harassing me today and I just feel like shit.”
“What were they saying?” Frank wanted to know.
“Just that I'm ugly and that I'm a freak and stuff, because of the way I dress and everything. It just really hurt my feelings.”
“You're not ugly, Char.” Frank sighed.

He didn't know how to go about “breaking up with” her, even if they weren't actually dating, when she was hysterical already.

“I feel really ugly,” Charlene said, “Honestly, I do. I'm not just saying that and searching for compliments, it's just how I feel.”
“You're actually really pretty,” Frank said apprehensively.
“Yeah, you say that and so do other guys who supposedly like me, but then something always happens. I just feel like I'm unlovable.”

Charlene was sobbing in front of Frank, and he was just getting more and more sucked into her sadness. He wanted to make her feel better, but he didn't know how. He didn't know how to tell her it wasn't working out when she was saying she was unlovable.

“There's someone out there for everyone,” Frank assured.
“Promise?” Charlene said in between sobs.
“Mhm,” Frank said and wiped away the tear on her cheek.
“Do you really think that I'm pretty, Frank?” Charlene asked.
“You're very pretty,” Frank said honestly.
“Prove to me you think so,” Charlene said with depression coated in her voice, “Because I honestly don't think anyone could find me remotely attractive.”
Frank sighed, “How?”

Charlene leaned in and kissed Frank, catching him off guard. He pulled away from her, stopping the kiss short.

“Charlene-” Frank started.
She started to cry, “See?! I'm so hideous you won't even kiss me.”
“It's not that, Charlene I just-”
“Please, Frank?” she pleaded, “Just... please?”
“Please what?” Frank asked, his eyebrows scrunching together.
“Please just kiss me.” she begged, “Please. I just need to feel better and you... you can make me feel better.”

Frank sat there in thought for a second just looking at Charlene. Her makeup was running down her face, and it reminded him of himself. He just wanted to feel wanted so bad at one point in his life, and he remembered the desperateness he had felt during that time. He suddenly felt sympathetic for her, despite how conflicted his thoughts were. He was there for a reason, and yet the reason seemed to be slipping further and further away from the front of his brain.

“Don't cry anymore, okay?” Frank said and wiped the makeup from under her eyes. “No matter what happens.”

Charlene nodded silently and Frank gently kissed her cheek. She took that as permission to bring her lips to his and kiss him. They kissed for a few minutes as they slowly got more and more into it. She started rubbing Frank's jeans, once again surprising Frank as the friction increased. Being a man, Frank's body started reacting, the animal instinct kicking in. As she increased the pressure the whole point of going over to her house got lost in Frank's clouded thoughts. He gently climbed on top of her as she took her shirt off, revealing her bright red bra. Frank allowed his hands to admire her chest, feeling the soft fabric of the bra as well as the softer skin of her boobs. She wrapped her arms around Frank's neck and pulled him in to continue kissing him.

Frank suddenly realized what he was doing and stopped himself, removing his hands from her chest and parting the kiss.

“I can't.” Frank said in more of a whisper than he anticipated.
“What do you mean?” Charlene said confused.
“I can't do this,” Frank tried to convince not only her but himself.

He neglected to remove himself from on top of her. He looked at her face but avoided her eyes.

“Prove to me that you think I'm pretty,” Charlene coaxed and shoved her hand down Frank's pants immediately making skin to skin contact while simultaneously guiding his hand to her boobs once again, “Even if it's just this once.”

Frank's body continued to harden as her hand pumped him, clouding his vision once again.

“Just this once,” Frank repeated.

Second try.

"Hey, can we talk?" Frank texted.
"Sure... everything okay?" Charlene asked.
"Yeah, meet me at the park, okay?"

He was clueless as to what he was going to say, or how he was even going to say it. He especially didn't want to hurt or insult her, but he knew it was time to cut the ties with Charlene.

He walked slowly to the park. He purposely crunched the leaves under his feet, somehow gaining satisfaction when they crinkled under his weight. The wind was nipping, going straight through him, completely unforgiving to his bones and teeth that were chattering. He continued walking. He knew what he had to do.

Before he could even comprehend it, he was already at the playground. Charlene was already there, swinging on the blue swing under her by herself. Her hair was tucked in a messy bun that was progressively getting messier as the wind blew it around. Her jacket was a good two to three sizes too big, and her pants were really tight. She had almost no makeup on, other than the bright lipstick that overcompensated for the absence of the rest. She turned her gaze up to frank apathetically, trying to read his eyes, but desperately failing. Her lips turned into a lazy smile as she watched him sit next to her.

"Hey, you." She directs towards him, not really looking in his direction.
"Hi," Frank sighs, "How are you?"
"I'm okay," she retorts, "Cold."
"Yeah, it's really cold tonight," he agreed awkwardly.
"Wanna talk in my car?" Charlene asks and nods in the direction of the parking lot.
Frank nods," Sure... yeah that sounds better than trying to thaw my balls off of this swing."
Come on, let's go defrost, then." Charlene said with a smile, it growing when Frank returned with a smirk of his own.

They got into her Ford Edge and she turned on the engine to put on the heat. Frank sat in the passenger side of the car and warmed his hands up near the air vent. Charlene smiled and rested her head on the head rest behind her, closing her eyes before opening them to see that Frank was staring at her.

"What?" she said and giggled, "Are you okay?"
"Yeah, why?" Frank asked.
She shrugged, "I don't know, you seem weird."
"Weird," Frank repeated, "I'm sorry..."
"It's okay," she said and laughed, casually brushing her hand over Frank's hair.
He smiled and grabbed the same hand, "Your hands are really cold."
"I thought we already went over how cold it was," she teased.
Frank playfully rolled his eyes, "Shush."

Charlene laughed and returned her hand to her lap. She turned up the radio and started humming along to the tune of the song. Frank's mind started to wander about how he's supposed to bring up the fact that he can't see her anymore, at least not in the way they'd been "seeing" each other lately.

The car got hot quickly due to the heat on full blast, causing Charlene to sigh and take off her first layer of jackets and turning the heat down. She now was in just a long sleeved shirt, showing her collar bones off nicely. Frank couldn't help but notice; collar bones being his favorite thing to admire on the body other than someone's eyes, which he ended up looking into hers.

"So, is everything okay?" Charlene asked, trying to figure out why he'd called her so late at night.
"Yeah..." Frank managed to say, but his thoughts were elsewhere.

She smiled and nodded, not really sure what she was supposed to do. Frank suddenly cupped her face and rubbed her cheek. Her skin prickled under his touch, but it was silky and flawless other than that. His eyes went from her's down to her lips. Without thinking too much about it, he kissed her lips softly. They were glossed with her lipstick; gentle and feminine; soft and girly. Something he had missed deep down in the back of his mind.

He kissed her deeper, leaning his body towards her's and rubbing her cheek with his thumb. The car's center console uncomfortably dug into his abdomen but he chose to ignore it. Her hand went to his shoulder and she started to rub it with her own hands. He continued to kiss her, tongueless, but without separation.

She initiated the first part of the removal of the clothes. Frank's jacket quickly left his body, his shirt not long following after. She took off her own shirt, only being left with her bra and his shirtless body. Charlene started kissing Frank's jawline, smearing her lipstick all over his skin. She kissed his neck, flicking her tongue skillfully before whispering into his ear.

"Move the seat back," she seduced and Frank complied without a second thought, moving the seat as far back as he could, and reclining it as well.

Charlene, due to her petite stature, climbed over the console without any problems and put her knee between Frank's legs on the seat, hovering over his mouth at the same time. She looked at him before deciding what she wanted to do. She kept her knee between his legs as she put just enough pressure between them to make Frank notice. She smiled before kissing him, rubbing her knee carefully in just the right spots. She soon crouched near his crotch, unzipping his pants, soon followed after her own pants coming off.

Third try.

"Thanks for meeting me." Frank said uncomfortably.
"I'm not used to seeing you in the day so much anymore," Charlene said with a smirk and winked.

Meeting her in the day was intentional. He knew he would be able to stay focused when there were lots of people around, and the sunlight wasn't able to hide certain activities that were technically illegal.

"Yeah," Frank chuckled uncomfortably."
"Well, I'm glad you invited me to lunch," she said and ate her salad with fruit she'd ordered, "I needed to tell you something."
"Hm?" Frank said and ate his fries with ranch.
"My family is going down to Colorado for a little while. I was thinking about going with them."
"Oh, really?' Frank answered, still trying to figure out how to get out of this.
"Mhm. I was wondering if you wanted to come? My mom said it was okay, and stuff..." she said and smiled.
Frank shrugged, "I don't think I can."
"Oh, okay...." Charlene answered, defeat heavy in her voice. "Maybe next time."
"I don't think so." Frank managed to say.
"Oh?"
"I can't, I mean. I can't." Frank stuttered.
"Can't" she questioned.
"I can't do that. This."
"This?" she said and cautiously took a drink of her water.
Frank sighed and dropped his fry, "I'm sorry."
"It's fine, Frank, you don't have to come to Colorado. I don't want you to think it's weird for me to ask, I'm sorry..."
"No, I don't mean Colorado, Charlene, I mean I can't do this... with you... anymore."

Frank refused to look at Charlene the entire time he stuttered that sentence. He couldn't. He was being a coward, and he knew it, but he didn't know how else to be. Charlene was silent for a while, causing Frank to finally look up at her. She was moving around a dried cranberry, chasing it around her plate with the fork, but not actually eating anything.

"I'm sorry," Frank managed to get out and sighed.
"So, is that what you've needed to talk to me about for.. the past couple of days?"
Frank automatically nodded, not thinking too far into it, "Yeah..."
"And, instead you just let me come onto you for days now, just using me for your own pleasure."
"What?!" Frank almost choked, "What? No, no, Charlene it's not like that."
"Oh, really? Because you could have said no, you could have told me that you wanted to break up or whatever the fuck we are without having sex with me. Instead you let me look like a fucking moron and like a whore or something."
"Charlene, I don't think you're a whore! I didn't mean for that to happen, I mean... I do care about you otherwise I wouldn't have.. engaged in that stuff... but I just... I can't be with you right now, and I'm sorry."
"Is there someone else?" Charlene fumed.
"No." Frank said and shook his head, "I just need some time to clear my head. I've had a lot of shit going on. It's not fair to you to drag you through this."
"Instead I'll just be your fuck buddy. Cool." Charlene said, "See you later, Frank."

Frank watched as Charlene walked out of the door, the bell jingling as she walked out. He clawed at his eyes and sighed.

"Fuck," he whispered to himself.
"Ready for your check?" his waiter asked hesitantly.
"Yes, please."