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Chi-Town Date with Aziz Ansari

I dare say that Aziz Ansari has played a critical part in my relationship with Steven.

When we first started dating, Steven and I were 24, both freshly returned from living abroad, newly employed in the US workforce, living on our own, and embodying everything there was to embody when you are a mid-twenty-something. Our dates consisted of cheap beers, taco nights, late nights out with friends and did I mention cheap beers?

A live Aziz Ansari show was the first big date activity Steven and I did together that didn’t involve a bar. It was revolutionary.

Ok I lied, there was a bar… but it only played a small part in the date.

I don’t think Steven ever really found Aziz that funny… He tolerated how highly I spoke of the Parks and Rec star, and fake laughed as I repeated his jokes over and over again.

Fast forward a few years, and Aziz has come out with a Netflix original series called Master of None. I watched the first season in a weekend (if you haven’t seen it, I highly recommend it) and had a whole new arsenal of jokes to repeat to Steven. I had to! I knew he would never want to watch it.

Until he did. A comedy miracle happened 3 weeks ago when Steven agreed to watch an episode…or 2…or 10.

After, he was officially an Aziz fan.

In an episode appropriately called “Nashville” (no spoilers, don’t worry) Aziz is advised by his friends to take a girl he is interested in on a weekend date to, you guessed it, Nashville. Aziz is reluctant (because seriously, a weekend trip for a FIRST date? Aggressive!) but decides to go for it; he finds cheap plane tickets and sweeps her away for an unforgettable weekend.

And so after we watched that episode, Steven and I had a strange desire to just pick up and GO somewhere. We, like Aziz, found cheap tickets online ($69) to Chicago and before I knew it, we were on our way (and I got to check off another item in my 52 tri-s in 52 weeks!)

We don’t ever do things like this, so I just wanted to say “thank you” to Aziz for inspiring us to stop being boring and lazy….and what better way to say “thank you” than to bring him along our trip!

We left work early on Friday and headed up to BWI to catch an early evening flight to Chi-town. Aziz was so excited!

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When we landed, our first stop was to grab a famous Chicago deep dish pizza. We opted to go to Gino’s East (per suggestion of a Chicago Native) and were not disappointed.

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I’m not sure I can compare deep dish to normal pizza…they are just so different…but delicious nonetheless. I was a total n00b and ordered a medium for the 2…I mean 3 of us. We ended up having half of a pizza leftover. Aziz and Steven definitely didn’t pack the food away like I thought they would. It was fine though, we got it boxed up and planned to put it in the refrigerator that Steven said we had in the hotel room.

But it wasn’t fine. There was no refrigerator. It was a devastating blow; a half of a delicious deep dish pizza that was going to go to waste. I went out in the hallway to find a trashcan to throw it away, but there was none to be found. I came back into the room and told Steven I would regretfully throw it away tomorrow when we left.

We woke up the next morning and Steven was still really upset about pizza. I’m not kidding when I say I have only seen him that upset like 2 other times. He just sat there, staring at the pizza. And then Aziz convinced him to do it…to just eat it.

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And so he did. I was real nervous about what the repercussions of eating a 7 hour, unrefrigerated old pizza were going to be. I asked Steven if he was still going to want to go to breakfast. I should have known the answer was “no.”

So I had breakfast in my room too.

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After deciding we were in clear, and that the pizza hadn’t poisoned us, we headed out to Willis Tower– the tallest building in the western hemisphere. I’m pretty sure I had been to this building (then called the Sears tower) when I was little but Steven and Aziz hadn’t. So, we headed up 103 flights to the top!

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The heights had Aziz a little nervous.

So i assisted him when we went out on the glass floor. This part was super kewl.

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After checking out the sights, we headed to Intelligentsia to grab a coffee. It was a really cute place that satisfied my need for some cold brew. Steven and Aziz split a beautiful cappuccino.

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One of the nicest parts of this trip was taking our time and not having any obligations– it’s very rare that on vacation, there are zero plans…but that is how this chi-town date was going to go down; I loved it! We decided our next stop would be Millenium Park and to check out what all the hoop-lah was about.

I had seen Could Gate AKA “the bean” in many pictures before. I chalked it up to something that people really hyped up but that actually wasn’t that cool.

I was so wrong. The bean was awesome!

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We spent a good amount of time here snapping photos and taking advantage of the BEAUTIFUL weather.

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We listened to some music and watched the ice skaters.

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After Aziz got his fill of people watching, we headed over to the Jay Pritzker Pavillion. Nothing was happening but I can imagine that this place is awesome during the summer and during concerts. Aziz was sweet enough to give us a little impromptu show.

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Time flew by here as we took in the amazing skyline.

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After, we headed over to Lake Shore Drive to rent some bikes and cruise along the water. The Triathlon gods knew I had taken the weekend off…and reminded me quickly to get back to it when I got home.

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We biked along the water for a bit and then got back on foot to walk toward the aquarium and planetarium.

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After a long walk, we grabbed lunch and drinks at First Draft. We couldn’t decide what to get but ended up splitting the fried chicken sammie and a cuban. Both were delish!

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Due to the impending food coma, we headed back to the hotel for a nap. After, we met up with Steven’s family friend, Jordi, who is in med school in Chicago. He took us to the west loop for dinner and drinks.

Every person I talked to about Chicago mentioned The Girl and the Goat and the Little Goat Diner.  The Girl and the Goat was out of the question…apparently you need reservations months in advance…

So to the Little Goat we went!


I had some bangin’ “Elvis Waffles”: Chocolate, bananas, peanut butter, bacon and maple syrup. I was happy to share with Aziz.

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After dinner, we headed to The Betty– a cool cocktail spot.

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It was great seeing Jordi again (it’s been about 2 years!) and we were so grateful to have someone showing us the neighborhood. I was stuffed by the end of the night. We said goodnight to Jordi and hopped in a cab to go back to the hotel.

The next morning, Steven’s cousin and her lovely family showed us a few more Chicago neighborhoods, took us to breakfast and dropped us off at the airport. We had a fantastic time. We also snapped our last Chicago picture!
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All in all, we had a fantastic trip. It was so fun being spontaneous, spending time with Steven (and Aziz) and catching up with some great Chicago peeps.

Thanks for this last pic, Steven…and Aziz.


Happy Tri-ing!


  1. OneDizzyBee says

    Glad you enjoyed Chicago. Morning-after deep dish is the best! Also, I’ve lived here all my life and never had the guts to stand on that glass floor at the top of Sears (real Chicagoans refuse to call it W…ll…s.)


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