One

As pumped as I am about this plan, I decided to ease myself into it by asking out a friend of friends. One is a tall, skinny, handsome guy-next-door kind of dude. He’s intelligent and witty, and I absolutely adore wittiness. I’ve never gotten his phone number, and I only ever see him in group get-togethers where we always make each other laugh. I definitely had a crush on One when I first met him; I have no idea what he thought of me, maybe that I was an energetic loon because the first time he saw me I was walking into a small house party with a container of cookies proclaiming something like, “Hi! I’m sorry I’m late, but I made cookies! I'm Penelope. I think I only know two of you here, so I’m going to need you each to tell me your name and two fun things about you.” True story, that’s how I roll. Since then and our previous group outings, One assumes that I always have an icebreaker ready at any moment. It’s not really my intention, but he’s kind of right. Anyhow, One was in a relationship at that first meeting, but since then he’s been dating around while working on his MBA, so I figure he’s a safe bet. Since I don’t have his number I decided to ask him out via email – so traditional, I know.

To: One

From: Penelope

Subject: Random idea

one! let's go on a date! not like a "we totally have a connection" date, but more of a "we're both fantastic, so why the heck not" date. seriously, let's go on one date just for fun.

i'll be on my best behavior and will even leave my sneakers at home. what do you say?

also, hi and how are you?

I might be horrible at using at capitalization, but at least I’m to the point, right? One responded a few days later…

To: Penelope

From: One

Subject: Re: Random, fun idea

penelope, a smashing idea except i'm way slammed with school and in the midst of a brady-bunch-esque love triangle: i'm thinking about taking two dates to prom but keeping them in separate rooms so they won't know the other one is there, think it will work?

In addition to being witty and sharing my lack of email capitalization, One is also diplomatic. No date, though. Moving on.