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10/11/2010 11:59 am ET | Updated Nov 17, 2011

Fifty First (J)Dates: The Biggest Loser

Fifty First (J)Dates
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Thank you to the FFJD fan who emailed this! I am telling it in my own wordz/parenthetical bouts of crazy.

Every day after work I manage to drag myself to the gym to plod along the elliptical and read Us Weekly. I am usually in an ugly, old sorority tee and leggings that specifically always have a hole in the Pikachu and I don't notice until I'm doing sit-ups and I can see myself in the mirror and I'm like zomg there are my granny panties for the one hot boy in the gym to see who happens to be standing behind me doing squats. Whatever.

So I'm there nearly every day, and I tend to see the same people around - the old guy who wears a matching grey sweatsuit, specifically because grey is the color in which sweat is most and readily apparent, the middle-age woman who decides pearls are a good thing to sweat on, and one very toned and athletic woman who runs on the treadmill next to me and makes me feel inadequate and fat.

The highlight of my day is seeing the hottest trainer, let's call him Dave, manning the front desk. Dave is hot, (for DC.) He sort of looks like Jake Gyllenhaal, if Jake worked on the Hill, were slightly uglier, and came from a random part of Westchester. I usually stick to the shrimpy Jewish men, and Dave is a nice welcome change, with his very large biceps. Dave always greets me with a kind, "nice to see that you're getting more intellectual with your People Mag instead of Life & Style," and waves. I sort of take this to mean that he wants to remove my leggins in a fit of passion in the steam room (which is really way too steamy. Like how are you supposed to breathe?)

Anyway, I decide, because I have had a terrible day because my boss told me I suck at life and relegated me to fetching chicken sammiches for the entire office, that I am going to take my anger out on the elliptical.

I head to the gym, where I see my Jake's Slightly Uglier Brother With Buns of Steel. I guess I have chicken sandwich anger bubbles above my head or something, because Dave asks me what's wrong. I relay my shiteous day to him, and he looks mildly sympathetic.

Then, even in my fantasies with Fake Jake G., I never imagined that he would invite me to have drinks with him and some "training buddies." It took me a second to register. I almost leapt over the reception desk, but I tried to play it cool. What do trainers do for happy hour? Do you put shots of vodka in your protein shake? Do you challenge each other to push-up-while-chugging contests?

I squeeze in a quick workout and call my roommate immediately. I need to foster a look that says "I'm hot but whatever I wear a Nike watch because it's the best instrument for my triathalons." (And by triathalon, I mean trifecta of frozen yogurt, Intermix, and Barneys, on repeat.)

I meet him at the bar nearby and it's weird to see Maggie G's Half-Bro in regular clothing. My heart flutters a little, just like when I work out for too long and realize I've run out of pages of the Britney Spears Hair Extension Disaster spread in InTouch.

"Hey, Jess!" Eeeeeeeeeee. (Giddy exclamation that defies the English language goes on in my head.) "This is my girlfriend, Amanda."

F...M...L.

Amanda is taned, toned, and tiny. I just assumed she was a trainer buddy. But my date has brought his girlfriend along. Which is always fun. (This happened to me, Meredith, once in Argentina. I invited a boy I had a crush on to a fun party and he texted back, do you have an extra ticket for my girlfriend? Womp.)

I tried to keep up, chatting about what little I knew about the fitness world, which is about three things, including the Biggest Loser. I felt like the Biggest Loser. Except without the miraculous weight-loss, subsequent body dysmorphia, and fitness equipment endorsements. As we headed out of the bar, I thought about what I was going to do when I saw Dave the next day.

I was slightly tipsy, and out of the corner of my eye saw a beacon of glimmering hope that could rectify this awful then awesome then back to awful day. "I'll catch you guys later," I said to the crew of bulging triceps.

Ben's Chilli Bowl was calling my name. And I sat in the booth, smearing cheez on my friez, I thought to myself, "now this is more like it." I got cheez on my Nike Triathalon watch. I didn't care. It tasted like victory.

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