It's a small, small world.

If it's true what they say about this being such a small world, then I am certainly correct in telling you that this city of 9 million people... is even smaller.

Case in point:

After a string of dating guys that decided to simply drop off the face of Manhattan (what am I doing wrong?), I decided to just suck it up and really start initiating that ever-so-brave first email via my Match.com account.

Enter: Midwestern Boy(*). We've had some pretty good emails back and forth to each other for the last week, and tonight's email is the one that I expect to hold my invitation for dinner or a drink this upcoming week. I decided to send my latest reply to him today right before I headed out to my exercise class in Union Square, and even took the time to mention to him at the end of said-email where I was headed for the evening.

Fast forward a couple of hours: I leave my class feeling fab, super energized and like I'd had a great workout. Sweaty? Yes. Hair in a pony and bangs pinned back? Check. Dance leggings, loose t-shirt and a sports bra? You got it. I've got the iPod in, some tunes blasting and I make my way underground to catch the train home. While standing on the platform, I do the ritualistic scan of the crowd to see if there are any cute guys lingering, and lucky for me, there is one. I don't have my contacts in, but I recognize that he's nicely dressed, probably in Finance like the rest of the male population in New York, and about six feet tall (my height minimum). Even though I'm schleppy looking from my workout, I decide to mosey his direction, and as I step through the same train car as him... Shit.

Oh yah, you guessed it. Platform Cutie was one in the same as Midwestern Boy. The subway car was fairly empty, so there was no ducking behind anyone or pretending that I didn't see him. I held my breath for the 20 blocks before his stop (the stop that he had mentioned in a previous email that he lived at, by the way), trying to figure out what the hell the odds of something like this really happening are (like 1 in 50 bazillion, I think), and hoping that he wouldn't glance at me for long enough to put two and two together and realize that the sweaty, messy haired and make-up-less girl across from him might actually be his date Friday night. He stepped off of his exit and didn't look back. He did check my online profile immediately after he got home though...

So, if that chance encounter hindered my chances for a weekend date, well, there might go another one... right off the face of Manhattan.

(*) Names have been withheld to protect the unsuspecting.