Jake, the Ladies and His Lack of Luck with Them

Second Grade: Jake found a note on his desk. The note simply asked: "Do you like me?" Below the inquiry were three check-boxes labeled "yes", "no" and "maybe". Jake was ecstatic because he saw who put the note on his desk. It was his crush, Kimberly. Jake hastily checks off "yes". When recess rolls around, he scans the playground for Kimberly. He spots her and rushes over with the note. Kimberly smiles as she talks to her friend Fiona, and notices Jake on his way over. Kimberly waves and Jake waves back. "I got your note," Jake says. Kimberly's smile turns into a disgusted smirk as Jake hands the note to her. "I knew it. I didn't want to believe it, but I knew it," Kimberly snarls, shaking her head disappointedly. She turns to Fiona; "Why do all the gross boys like me?!" Fiona shrugs as Kimberly slaps her forehead with her palm. Jake slowly turns tail and walls away, a frown slowly forming on his face that would last for a very long time.

Ninth Grade: Whenever his gym class has an "Unconventional Day", Jake gets excited. He loves all the weird sports that his gym teacher chooses to play on these days. Today, the sport is archery and Jake couldn't be happier. He collects his arrows, sets his bow and pulls back. Bullseye. Bullseye. Yellow area. Bullseye. "Fantastic job," Mr. Franklin shouts from the opposite end of the gymnasium. Jake nods, blushing a little as he heads to end of the line to wait for his next turn. He looks to the head of the line and sees Ashley. She's visibly struggling as she tries to set her arrow straight and lets out a loud sigh. Then she turns her head, looking down the line and directly at Jake. "Do you think you could help me, maybe," Ashley says sheepishly. Jake nods, "Of course." Jake moves up the line and to Ashley's side. He takes an arrow, sets it in her bow and hands it to her. "How do you stand though? That has a lot to do with it, right?" Ashley looks at Jake, puzzled. "Here just turn around," Jake answer. Ashley turns. Jake moves in behind her and nervously takes her hand, placing it in the proper position. "Good," Jake says as he moves a little closer, the front on her pants just brushing against Ashley for an instant. "Hey! What the fuck?" Ashley turns back around quickly. "I'm-I'm just trying to help you..." Jake manages to form, extremely embarrassed. "You just touched my ass! Mr. Franklin!" Jake turns and moves to the back of the line, slowly. "What's your problem, Jake?" Mr. Franklin shouts. "You could've at least asked for number first!" Mr. Franklin lets out a hearty laugh. Jake hangs his head as everyone on the line in front of him snickers.

Freshman Year of College: Jake's sister decided to set him up on a blind date. Jake is filled to the brim with a combination of excitement, horror and anticipation as he slips on his "date clothes." A green polo, classic blue jeans and, his staple, red Converse's.  He thanks his sister as he heads out the door on his way to Luigi's Italiano Ristorante. It's a small place with nice candles, dim lighting and waiters with fake Italian accents (or are they actually from Italy?) and funny looking bow-ties. Jake enters Luigi's and is seated by an energetic hostess ("Thanks for choosing Luigi's! We'll try our best to make you feel like you're in an actual Sicilian ristorante!") and taps his foot as he waits for his date. At forty minutes past eight (and exactly forty minutes late) and she falls through the front door. Literally. "Whoops," she exclaims, fixing her top as her bra nearly pops fully out. She scans the room and sees Jake who is now blushing. "You must be Jaaaake," she slurs as she clomps her high heels over to him. She gives him a sloppy hug and a lip-stick slathered kiss on the cheek and takes her seat across from him. "I'm Stephanie! Your sister's told me loooaaaadsss about you," Stephanie says, wide-eyed. "Oh, hi... Stephanie," Jake mutters, his cheeks blushing. "Umm... Are you... Okay?" Stephanie's expression goes from enthusiastic to teary in an instant. "No, Jake. I'm not. I just broke up with my boyfriend and my cat just died and I told myself I was just gonna have a sip of wine before I came to dull my jitters and I wound drinking the whole boooootttlllleee," Stephanie stuffs her face into her hands, all waterworks. Jake stares at her, expressionless. "Oh," he says as he slowly gets up from his chair and walks out the front door, a sour frown pasted on his face.