Time Machine to Last Labor Day

This time a year ago the BFF and I were wrapping up our Hamptons share experience with The World’s Biggest Douchebag and Some People We Didn’t Really Know. As things were winding down it became quite apparent the BFF and I weren’t BFFs with everyone like Memorial Day had led us to believe. It had been fun, but we were ready for it to end.

One major factor that aided to this sentiment was that the World’s Biggest Douchebag had landed the hottest girl in the share (who I had thought was way out of his league, but oh yay she was willing to date down. IAAB - I am a bitch). There really is nothing better than getting to witness first-hand your former fling and a girl way hotter than you become an item. And, since getting to watch their love blossom before my eyes was such a special treat, I was excited to discover that they would continue sharing their affection with the world via Facebook alums dedicated to their romantic getaways (in painstaking photo documentation detail too magical to avoid when it’s on your newsfeed). From the looks of their pictures, they seem to be made for one another. Oh burn.

Anyway, lucky for me, I had moved on so I wasn’t particularly crushed. Unfortunately the person of interest was not the best choice. Or even a good choice. Or even an OK choice. In fact, some people would probably go so far as to say he was the True World’s Biggest Douchebag (WBDB).

He was pushy, manipulative, bratty. He toyed with my emotions. He could be cruel. And that’s just how I first knew him as friends.

One time he told me he HAD really liked me. So great to hear that in past tense.

Even after that fun exchange, I still liked him. The first time we ever hooked up (after months of flirtation), he pretended like he didn’t know it happened. For weeks he kept that up. Yeah we were drunk, but we weren’t that drunk. Asshole.

And I was stupid enough to let it happen again. Obviously drinking was involved that time too. Yeah he must have really liked me. Again, I like to learn things the hard way.

Had they’re been an election for the WBDB title, he would have won the popular vote. But thanks to that one showing at the Bob Schneider concert, Jack’s status had been solidified. That concert was the state of Florida.


This guy was the Al Gore of my Summer ’08.

I may still make poor choices, but thinking back to last year, I’m slightly better off than I was then - at least the douchebags I go after now are of a higher caliber. High five.

Fingers crossed Labor Day 2010 is even better.