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.

The Plan

Ever since college, almost any time I tell a story about an interaction I've had with a guy, my friends laugh and tell me I should write a book. I tell them that my stories won’t be entertaining to people that don’t know me because, honestly, people that don't know me probably think I lean towards the crazy side. Then I came up with the idea of asking out one guy a week for a year. If the guy doesn’t say yes, oh well, it won’t be the first or last time. So yes, this is happening…not because I’m on the search for “the one,” but because why the heck not? Also because of all the guys I’ve kissed in my life, only one of them was my boyfriend. Seriously, I’m a bit of a free spirit and I’ve only had two relationships which both lasted three months – one when I was in 6^th grade (and we never kissed), and the second when I was 31 (we kissed a lot). Instead of going on dates, I usually tend to make out with a guy friend or a random dude that I’ve met. Plus, I moved to SF over a year ago and have even less game here (and by “even less” I mean zero, possibly negative game). I blame it on the fact that the majority of the male population here either also like guys or they are hipsters, and neither of those groups wants to date me. I can’t think of a thing I have to lose with this new plan. I love talking to strangers, I can try different methods of asking out guys, my friends and I will be endlessly entertained, and maybe I’ll actually go on a date (because the last date I went on was with my 2^nd boyfriend over a year ago). Really, the only possible kink in this plan is if one of the guys and I fall madly in love with each other, but hard-headed me forges on with this project and leads a double-life causing all sorts of nail-biting, frustrating chaos to ensue before we live happily ever after in the end (think romantic-comedy with Natalie Portman). Let the games begin!