Last Wednesday, I’d planned on doing a little celebratory drinking: A toast to midweek. My attitude: halfway to Friday is a glass half full situation, provided the glass is filled with alcohol.

The night was intended to be casual: just a couple of drinks with my girlfriend T, one of my best friends from high school. However, everything changed, crashed, and burned when T informed me that L, a male high-school classmate, would be meeting up with us. (Since becoming a Gossip Girl fan, I prefer to abbreviate names to the first initial. You know you love me.)

An introduction to T and L:

T is a close confidante who compassionately listens to my perpetual woes concerning the three Bs: boys, body image, and the ongoing debate of whether or not I should get bangs. As a mark of true friendship, she’s even agreed tell me if I’m getting fat. Plus she went to NYU, so T essentially acts as a sponsor for my one-man New-to-NYC support group.

At the opposite end of the spectrum, L’s a guy whom I never expected to have back in my life. I had a torturous crush on him in high school. Why? Because L did whatever he wanted and always managed to look flawless. He was president of the class and captain of the soccer team, yet he was also the giant Bear mascot on the sidelines of the basketball games. He rode a unicycle to school. L was some amazing crossbreed of Ashton Kutcher and Michael Cera: attractive, funny, and friends with everyone.

He was even friends with me, mostly because we had a lot of the same classes together. By senior year, I finally learned how to talk to L without feeling like English was my second language, but it never got beyond that.

The whole situation was such a high school cliché that I look back and cringe. So it came as a bit of a shock when T told me that she’d run into L in Trader Joe’s and that she’d made plans for all of us to hang out that night--as in three to five hours from that point in time. Walking down St. Marks, I flipped out, regressing to a bumbling teenager, and spilled all of my Pinkberry kiwi topping on the ground.

T had anticipated this reaction and stood there patiently, waiting for the preliminary shock to blow over. Sure enough, reason returned.

What was I so worked up about?

I had four years of college debauchery and dysfunction under my belt. I’m so over high school. So over it.

I immediately dragged T back to my apartment to select an outfit.

To be continued…