Chicago? My favorite city in the world.  Darewood and Chelle ? My two best friends.  And Man vs Food at the height of its popularity? Let’s call it the life imitating art imitating life component of our adventure

Darewood, Chelle and I were long overdue for a best friends get-together. Our spouses were kind enough to let us organize a little three-day get-away in the Windy City. You don’t have to tell us twice – we were off.

Sweet, sweet Chicago. Oh how I love thee!

For those of you still living in 1994, Man vs Food is a show where this guy named Adam Richman visits restaurants all over the country accepting their ridiculous food challenges, like drinking five gallons worth of milkshakes in thirty minutes or eating a seven pound steak in under an hour. Growing up, Darewood was just like the guy from Man vs Food. He had an endless pit for a stomach and would eat anything and everything in sight. Chelle and I were thoroughly convinced there was not a challenge out there that Darewood couldn’t meet. Then add  Chicago into the mix – a food metropolis. I mean you name it they have it, or are on the cusp of inventing it. Finding a food challenge wouldn’t be too hard.

But we had to find just the right challenge for our famished friend. I mean, let’s be honest, Darewood wasn’t a 16 year old basketball-playing  teen anymore. He was approaching the big 3-0. We needed to be a bit gentle for his first food challenge. We found it. The Big Timmy Challenge at Timothy O’Tooles Pub: two half pound burger patties topped with four cheeses (Cheddar, Jack, mozzarella and Swiss), bacon, onion straws, lettuce, tomato, red onion and BBQ sauce. The burger is also served with a giant pile of fries and onion rings. I would estimate each at about  half- a-pound. Eat all of that and you get a free t-shirt. Free tee? Say no more. Darewood was in.

As for Chelle and me? An all you can drink mimosa bar for the next two hours while hilarity ensues. Timothy O’Tooles rocks.

Mimosas in hand. We are good to go.

And so it began. It went a little something like this …

Part 1. Food arrives. Tastes good. Progress is made. Getting a little rougher … feeling a little full, but just over halfway there.

Chelle’s response.

Yeah, it’s pretty funny. Even without six mimosas encouraging the giggles.

The hat gets flipped. He’s serious now (seriously feeling ill).

Part 2. Pushing through. Food is cold. The meat sweats set in. Just a few more bites …

After nearly two hours, Darewood did it! And though the food was completely cold thirty minutes in, and  soggy by the end, he did it! Darewood got the shirt! He also proceeded to the bathroom as soon as the waitress handed it to him and left the table.

As Darewood was indisposed, Chelle and I waited for him by the entrance where we happened to see the exact same shirt for sale. In fact, it cost less than the food challenge itself. So essentially we could have just bought him the shirt and he wouldn’t be having a moment with the nearest toilet in the John. But what would have been gained from that? (other than the tee)

Now, I didn’t actually do the food challenge, but I was every little bit a part of the experience as Darewood was (just much less full). Sometimes in life you just have to say yes to the really big burger with some fries and rings. I will never forget how hard I laughed, the realization his stomach wasn’t what it used to be, the fact that he puked, or that we could have just bought the shirt for $14.95. But who can pass up a free tee? No matter what you have to do to get it? Darewood can’t. That’s for sure.