They both sat on the grass enjoying their cookies and cream ice cream when he turned to her.

"If we aren't married when we're thirty five, do you want to marry me?"

"Leo don't be stupid honestly why would I want to do that? Who would want to marry you?"

"Come on Naomi. It's only if we aren't married."

"I'm marrying a rich doctor." She smiled innocently and he turned to her.

"As if. You're gross and weird. You smell and your hair is always messy. Plus your face is chubby and you have no boobs." His insults flew at her and he grabbed her chest a squeezed. "Pancakes." She swatted his hand off her chest and stuffed the rest of her ice cream cone in his face.

"You're ugly and mean! You're unoriginal and not funny. You are so self centered and I feel bad for your future wife!" She shouted in his face and he couldn't suppress his laugh.

"Naomi you're so petty." He gasped slightly for air when she shoved her pinkie in his face.

"I'm not going to marry you. Think of this more of a challenge than a promise. I will get married before thirty five so I'm not stuck with your greedy ass. Being tied down with you is motivation in itself to find someone handsome and nice."

"Your expectations are a little high sweetie." He grinned as he wrapped his pinkie around hers. His smile hid the fact that he was quite surprised that she took the bait.

"Count the race on." She smiled confident that she would win.

-

"Leo! There is more to life than just hitting the books I hope you know." Leo's roommate shouted from the other room.

"So I can't cut past the-" Leo towered over his books as he brushed his hair back.

"Leo you need to get out of here. What is all this medical knowledge going to do for you when it comes to getting a girl."

"Take note Oliver. This is why you're single." Leo commented past the constant mumbling of anatomy and how the plasma in one's blood works.

"You are single too jackass!" Oliver smacked him over the head with a pillow, knocking his reading glasses off. "And why is all this medical school hoopla a shush shush hush thing?"

"That is also how you get the girl."

"Oh yeah? Then explain to me how you have not had a girlfriend since the seventh grade. Who was that girl who broke your heart?"

"Mention her I dare you." Leo slid the focals back on before he continued to concentrate on the textbook.

"How did the story go? Didn't she ask you out by using Shakespeare?"

"You're a fucking idiot."

"Romeo O Romeo-" His mocking tone of voice was cut off when the doorbell rang. Oliver jumped off the bed and ran to answer. "Pizza is here!" Oliver shouted back to Leo and Leo shook his head.

He stood up from his chair and grabbed his wallet.

"That'll be $20 please." The girl smiled and looked at Leo. She covered her face with her hat and quickly snatched the money out of his hand before bolting down the stairs.

"Naomi I'm not stupid I know it's you." He laughed and she froze in her spot.

She spun around on her heels and looked up at him. He tussled her hat slightly and her loose fishtail braid began to fall over her shoulder.

"How did you know?" She blushed in embarrassment as he poked her skin where the jaw met her neck.

"That cute little birthmark."

Oliver walked over to them with both of his hands in his pockets. He leaned in over Naomi and carefully scanned her.

"So you're the infamous Naomi my Leo talks about?" He questioned and she turned away.

"N-no." She lied and touched her chin.

"Liar." Leo crinkled up his nose and snorted slightly. "You still touch your chin when you lie?"

"L-leave me alone!" She pushed him away and continued to pick at her.

"Where is your dear rich doctor husband?" He asked and she looked up at him once more.

"Teacher and he is my boyfriend."

Then was when Leo came to that realization. His heart stung when that word slipped through her lips.

"I would love to meet him." He smiled innocently and she crossed her arms.

"And why should you? You have no importance in my life anymore."

"Thirty five Naomi. Your clock is ticking."

"Says the single one." She sneered at him and looked away.

"I want to meet this man. Not for personal reasons. I just want to meet the man I lost my challenge to."

His intentions were of splitting the two up. Age twenty, Naomi dumped her teacher boyfriend after he was caught cheating. Age twenty three, Naomi left her lawyer boyfriend after she found out that he was an escort. Age twenty seven, Naomi left her boyfriend of three years when he went abroad and got an Italian woman pregnant.

All these exposures were not accidental. Leo practically guided them to her.

Age twenty nine, she quit on dating anyone else. She lost contact with Leo as he separated himself from her in order to concentrate on medical school. His best interest was to succeed in such. He was not engaged with women or men as he knew who he wanted. His desired job was to become programmer. But he knew that wasn't in the realm of possibility as Naomi specifically mentioned a rich doctor, not programmer. Oliver got married to Naomi's younger sister and they were expecting.

"God dammit no milk." Leo slammed the fridge door shut and looked at the time.

He went to the store quick when he slammed on the brakes before the bridge. The street light light up a figure sitting on the rail, slightly leaning over. He ran out of his car and stopped in his tracks. The wind caught up and blew the dynamics of the figure, revealing a small birthmark on their neck.

"Naomi. Come over here." Leo walked over and she looked at him.

Her eyes were puffy and red and she leaned forward.

"Come near me and I'll let go." She threatened and he stopped once more.

"Hey I won't touch you. Can I sit next to you?"

She hesitantly nodded as he sat on the sidewalk facing away from her. Silence lingered before he brought up a subject.

"Hey. Want to go get ice cream?" He asked and she shook her head. "Cookies and cream."

She shook her head again and mumbled.

"How do you do it Leo?"

"Do what?"

"Life."

"I think of you."

"Don't be irrational."

"I think of the challenge I made you. I antagonized you on purpose. I was too afraid to directly get rejected so I made you promise me that. I know you never break your promises and so I knew that if you agreed, I'd get my chance with you Naomi."

She stared at the moon past the trees and he stood up.

"Naomi. I can't wait any longer. I want you to lose the challenge. I want you to lose it to me."

She swung her legs over the rail a jumped onto the sidewalk next to him.

"You're mean and ugly." She shook her head and walked past him.

"I'm also your rich doctor Naomi."

She stopped walking away from him and pressed the palms of her hands against her mouth. Silent tears poured from her eyes and she turned to him. His heart crushed under the pressure that he caused her sadness.

"If you asked me to marry you instead of that goddamn challenge, I would've then too."

"I lost I guess. I couldn't wait until thirty five."

"And I lost because I'm marrying you." She looked up at him as she always have.

He pulled her into a hug and mumbled into her ear.

"I love you Naomi Lynn."