DBAG DATING: The Story of Jake Gyllenhaal, or The New Year's Eve That Never Happened

Editor's Note: This very timely post comes from a new contributor to this blog, whom I like to call the Loggster. The Loggster is one of my best friends, earning her nickname for being one of the calmest, nicest people I know. (Log -> Boring person -> Loggster. Get it?!) However, she also shares my special Superwoman powers of ATTRACTING ALL THE WRONG GUYS, and so her voice on this site is highly cherished.

Dear Dbag Addict,

In response to your most recent inquiry, "What's the worst way a guy has ever broken up with you?", here goes my tale of the New Year's Eve that never happened.

A couple of winters ago, my best friend's hubby acquired a new single friend, which in single girl world means potential new guy to be set up with. (After all, what girl doesn't dream of a life of bff dinners and vacations, followed by everybody moving in next door and raising bff babies?) I was told that potential new guy was a nice Russian Jewish boy, had a decent job, lived in the trendy neighborhood of Williamsburg, and looked like Jake Gyllenhaal. I know what you must be thinking: how was he still single?

It turned out that my Jake Gyllenhaal was about 5'9 and on the chubby side, and talking to him was like pulling teeth. I guess he took a liking towards me, because he ended up taking my number and asking me out. My very first date with JG was terribly awkward. I had to do all the ordering (Editor’s Note: WTF?!) and, frankly, there is only so much time I can spend talking about myself. I just kept downing my martinis and praying for the torture to end. About five martinis into it, JG decided to kiss me, at which point I was too drunk to care. To my utmost shock, whatever my Jake lacked in social skills, he sure made up in the kissing department. And so, I let him take me out for a second date, and then a third and a fourth.

Throughout the course of the month that we continued to see each other, I had my doubts about Jake. Could we really try to create a relationship on sucking face? When I told my best friend that JG was socially awkward and we had nothing in common, she insisted that he was a good guy and urged me to give it a chance. Frankly, I think she was more excited about the newly budding bromance between Jake and her hubby.

With New Year's Eve approaching, I decided to hang in there. We were all suppose to spend the night together at a Russian restaurant, and I finally didn't have to pay for myself! (Editor’s Note: Russian restaurants in New York are a very fancy extravaganza that entail unlimited quantities of herring and vodka at a very high price per seat.)

However, a week before New Years, Jake Gyllenhaal mysteriously disappears. On December 28^th, I got an email from him saying that he was at the JFK Jet Blue Terminal, about to board a plane to Dominican Republic for New Years. (Editor’s Note: God bless you for saving this email.)