Pink Pitchers in Boys Town – Chicago Day 3

Considering the enervating walk of the previous day, after breakfast, we decided to explore closer to home. “Closer to home” meant limiting ourselves to the Lincoln Park area. Yet somehow we ended up on a 40 minute walk to Wrigley Field, passing through Boys Town. Boys Town was where we were planning to spend our night – and we may or may not have visited some naughty shops and some vintage shops along the way too. Tsk tsk, readers.

Anyone remember the movie Rookie of the Year? Oh my gosh, that was my shit back in the day. I remember in 5th grade we were allowed to watch movies during recess and everyone’s first choice was ROTY. Come on, you remember, it’s that movie about this pre-teen boy who injured his arm and subsequently gained some kind of awesome reflex (which sounded like a stretching rubber band when he was winding up) that made him the best pitcher in the state. So good that he was drafted by the Chicago Cubs! Since then, Wrigley Stadium had been some kind of “go-to” location for me. The setting for a favorite childhood film.

So passing by it was kind of cool. Even cooler was that there was a Cubs game actually going on! Walking through the neighborhoods, you’d see a sea of blue and red jerseys herding towards the stadium. Ironically I don’t enjoy the game of baseball too much (and neither do my friends), so it makes sense why we didn’t attend the game. It was so exciting to see the stadium packed and fans eager to watch their beloved Cubs. Even if we weren’t among them.

What was for lunch, you ask? More deep dish? No. More cupcakes? Thankfully, no. Even better! Delicious … grilled … frickin’ …. cheese from a joint called – wait for it – Cheesie’s. In Jacksonville, we have this popular food truck with specialty grilled cheese. It’s called “The Happy Grilled Cheese” and they post over social media where there truck will be visiting next. Specialty grilled cheese means that they’re adding bbq, mac & cheese, various meats, shoot, anything you can think of.

It’s expensive, but you feel happy afterward. That could have been the beer though.

We chilled out the rest of the day by watching Bob’s Burgers and prepared mix drinks45db01e7815b388a17c883f9278bd3e6_400x400 that we would divulge in before going out on the town. Boys Town, to be exact. This was one of the things I was most looking forward to before getting to Chicago. The only bars I have been to are filled with either sloppy frat boys or brooding hipsters, nothing too indelible. But a gay bar? No, I have never stepped foot in one before. And frankly, I was super excited! Jacksonville has openly gay individuals, of course. But, nowhere near as open as in Boys Town!

I wore a blood-orange-maxi-dress (NOT with heels, but my gladiator sandals, because my feet were killing me mind you. And, remember, that Boys Town was nearly a 30 minute walk away) and my hair in a twisty-bun-thing. Elena said I looked like a Grecian goddess, which I will totally take. I was excited to go out and dance! (*cue Dane Cook* “I JUSS WANNA DUNCE!”) We spent a lot of time at a bar called Roscoe’s Tavern – we danced on stage and the music was bumping the whole time. Oh, it was so much fun! So much better than any other bar experience I have had – no weird, nasty guys creeping on you. Rather, it was cute gay guys telling you that your outfit was on point or that they love your hair! Like, what?! The night started slipping away after we had our second pink pitcher of alcohol. Let’s just say that the walk home was a memorable (or can we say that?) one! Such a fun time with my friends who I have never gone out with before. If this picture below doesn’t summarize the whole night, I don’t know what will.


I have a story to tell. It was my most favorite, most memorable part of the night. In the center of the bar, there was this beautiful asian girl donning a tight, red dress with the highest pair of stiletto heels I had ever seen. It was after she waved to a group of onlookers, that I looked back and saw those same heels heading into the boys bathroom. We all looked at each other like, “Yeah, girl!”. Girl was a boy in drag! Don’t you hate it when they look prettier than you?! Haha. Anyway, later that night, I go into the girls bathroom to break the seal, and LO AND BEHOLD, it is the SAME girl from earlier. I sidled next to her as we both washed our hands in silence. She turned over to me, touches my shoulder and says, “You are so pretty! I absolutely LOVE your dress.” It was when I responded with, “Thanks, girl, you too!” that she wiped her hands, made her way to me again, and blew me a kiss. Like, I could feel her breath in face. I cornily pretend caught it and smiled as I watched her sassy-walk right out of the bathroom. I will tell this story whenever I get the chance.

Danny told us the normally 30 minute walk home took us about an hour. My Grecian goddess look turned into a wet-mess. And we went to sleep in the living room.

Successful night.

What are your favorite going-out memories? Ever gotten a little crazy in a city that wasn’t home? Let me know all about them!



Walking 12 miles and Wishing I Knew How to Ride a Bike / Chicago Day 2

I had prepared myself to walk. It is a big city, that’s what they do there. But I was not prepared for the journey I would take on this day. When we first arrived in Chicago, Danny texted Elena saying, “Tell Tiffany it’s really easy to get around on bikes! We can take trails…we can take them downtown…we can…”… At that point I blacked out. Ride bikes?! No one told me we had to ride bikes! Panic set in.

For those that know me, it’s common knowledge that “Tiffany can’t ride a bike.” It’d go something like this: “Hey, want to take our beach cruisers out on 4th of July….oh, wait, that’s right, you can’t!”. It goes from “Oh, I am so sorry for you!” to “LMFAO, WHAT A N00B!”. Haha, it’s okay, I take it all in good fashion. 20+ years of jokes kind of get old and my feelings don’t get hurt that easily anyway. Perks of having a family that jokes around all the time; you don’t take anyone too seriously.

Even though they probably both held secret grudges (not so secret on Danny’s part, he jokingly let me have it with snide remarks about my two-wheel fears), we walked. We walked everywhere. Because I do not live an active lifestyle, I have no clue how I did it! Apparently iPhones have a Fitness app that counts how far you have walked and how many steps you have taken. My phone was in my purse, so I don’t think it was totally accurate, but it counted 25,000+ steps in 10+ miles. Regardless, I felt really bad that I had to be the bitch that kept everyone on foot.

What We Saw in Downtown Chicago

DSC03352I will have to say that Chicago’s skyline is pretty incomparable. If you didn’t know, I have a thing for skylines. Some people may argue that they all look the same,but they absolutely don’t! Yes, they are just a bunch of buildings lined up together. But can’t you see the difference in height? In color hues? In the way the sunsets peek through? Take a look at LA’s skyline or New Orleans’: totally different! Plus, Chicago has those two spikey thingys poking out from on top of the John Hancock building. That’s freaking hilarious. They look like antennas! Anyway, this was my view as we were walking down the long ass trail to downtown. We passed by this large body of water with artificial waves and sand attached to it, or as they like to call it a “beach”. I am from Florida, so I have to be a little partial to the real salt air and seashell-ridden sands. But, hey! I will give it to Illinois. They make do with what they got. There were girls in their bikinis attempting to tan and boys playing frisbee. Closest thing to the real thing that you can get, I suppose!

Downtown Chicago was how I imagined it. Bustling crowds attempting to make their way through the maze of skyscrapers. There were a lot of department stores and a lot of people coming out of their doors with more bags than they could carry. As I watched everyone scramble across the city and cross eachother’s paths so quickly, I found that it was difficult to tell between who were real Chicago inhabitants and who were the tourists. I don’t know if that is a good thing or a bad thing.

I will say I give props to every pedestrian crossing the busy streets. I second guessed myself every time I had to cross. Danny was so good at predicting when lights would change, he always bravely put his foot forward and trekked across that road as if he owned it. I never gained that confidence, so I always just blindly followed him. Probably not a good thing because there came a point when I wouldn’t look right or left and just trailed after him like a baby following mother duck. Death for the followers.

Where We Ate in Downtown Chicago

Genuine Chicago Deep-Dish

When you think of a signature Chicago food, what comes to mind? Yep, deep dish. We went to Pizanos on Madison Street for my first taste of Chicago pizza. Back home in Florida, on Thursdays I have a group of friends that always goes to a pizza place called Al’s for dollar slices and beers. I sent them a picture of my meal, not entirely sorry I was missing out on our usual dinner together. “Having a slice for you here in Chicago”, I texted.

However, I am not going to lie I was not super impressed. It’s funny because we actually originally ordered a thin-crust pizza but, because the waiter was new and confused, we got a deep dish instead. So we take what we are given! If you don’t know what deep-dish pizza entails, it is actually exactly what it sounds like. Chicago-style pizza is known to have high edges and a thicker tomato sauce. To most, that sounds like a party! But to me, a lover of hand-tossed or thin-crust with light tomato sauce, it wasn’t that enjoyable. Don’t get me wrong though! I like pizza as much as the next person! Imma nom-nom-nom that up faster than you can say “Yo, get away from my plate”. But I didn’t like how doughy it was. Just not a great aftertaste. Tell me if anyone out there agrees with me. If not, I am okay standing alone.19520749379_39e353f4cf_o

Ever seen a Cupcake ATM? Who needs money?

For dinner we had the very-healthy Sprinkles Cupcakes. I don’t remember why we didn’t have a real meal. But I think it had something to do with the fact that our feet hurt SO bad, we had to sit down and soak our feet for a good portion of the night. I remember getting home and being like “What is walking? Why do we do this?”. We probably were like “Getting up is required to get food? Naaaaaaaah.”

Do you have any experiences like this? Let me know in the comments.

Ending the night with a feet soak

Here’s to bike-riding. Cheers.



Rooftop Railroads & Comfort of Old Friends / Chicago Day 1

If a friendship lasts longer than 7 years, it will last a lifetime.

I woke up this morning not remembering where I was. Oh, and with my leg splayed over my friend who doesn’t like to cuddle. Over dinner the night before, we all discussed what our strange sleeping habits are. I assured her that my only weirdness is somehow ending up diagonal in the night. But, much to her chagrin, I was wrong. I apparantly also inadvertently trespass on other people’s space! When we woke up, I asked her how her sleep was and she responded coyly with “Danny’s bed is super comfortable…..oh, and, you lied, you ARE a cuddler.” The smile on her face had meant she was taking it graciously though. I gave her permission to kick me next time. That usually works.

Our home for the next 4 days would be on the bottom level of a 3 story apartment in Chicago. Even though my phone displayed that it was 7am, the room remained pitch black. I pondered on how this was possible for a while, but upon looking around the room, I realized there were no windows. So weird! I did sleep well though, having recovered from the night before. Danny’s boyfriend Chris had cooked us an amazing meal for dinner (ending with some rum-soaked peaches topped with homemade whipped cream for dessert. Only I didn’t taste any peaches, if you know what I mean). The only home cooked meal I have had for a long time.


Flashback to when we first arrived at Midway International Airport: it actually was not a struggle at all. From Jacksonville, it was an easy 2 and 1/2 hour direct flight! What I was most worried about was using the trains. Or, as tourists from smaller cities know them, dreaded public transportation! I was already preparing myself to get lost in the subway. I tried my hardest not to look like a tourist. But it is hard not to when you are constantly looking around and jumping at the sound of every stop made. All I kept thinking was “Well, at least I have a change of clothes! Ugh, this luggage is heavy. No! Not more stairs! I wonder if they have any restaurants in the trains for the tourists who get lost on their journeys?”. Obviously I was confident. Per Danny’s directions, we took the Orange Line to the Brown Line. If you know what I am talking about, good for you. I am glad I had Elena with me because what I was imagining was a kid drawing literal orange lines and brown lines on the sidewalk. I don’t know what to do with that!

When we finally made it to Danny’s street, I was in awe of how cute it was! If you don’t count the constant clattering of the train tracks (which eventually turned into white noise), it is an incredibly quiet area. If Danny’s blinds weren’t open, I wouldn’t have had any clue that other people choose it as a route to their destinations. I couldn’t wait to make our home in a real Chicago abode.

I had expected to eat well in this city. If I had a shitty time or didn’t enjoy any of the architecture, I could live with that. But if the food was subpar? Take me back home. My first taste of Chicago was at a taco joint called…”Taco Joint” on North Halstead Street. And…it…was…GOOD. Ever had a salmon taco? Me either. But I had a delicious ceviche taco! We paired it with a beer-mixed drink called “Traditional Red”. We were disappointed because there was no wine it in, having thought we ordered a SANGRIA. But, when I read the menu again, I realized it said SANGRITA. So it all makes sense now.

My dad would be proud of my Modelo. It was a spicy wake-up call!

One thing I will say about Chicago is there is FREE STUFF EVERYWHERE. Literally, the minute we walked into the FREE zoo, there were girls handing out FREE cans of Red Bull. It just so happens that all of this was taking place in a FREE country! Kidding. But I could not believe that the zoo was free: there were no gates, no entrance fees, and no one to check your tickets. It wasn’t a small, janky zoo with sad looking animals either! They had rhinos, penguins, polar bears, meerkats, and a lot of other exhibitions that the Jacksonville Zoo does not have. And I cannot tell you how wonderful it is to enjoy a zoo without sweating your face off in 90+ degree weather!

Located on North Clark Street. They are open most days from 10am – 5pm.

When the night winded in, we headed over to Chris’ house. Two words: Bachelor Pad. To the max. He had a chalkboard wall adorned with business plans and a list of “Places to Go”. In the bathroom, there was a makeshift lamp made out of an old wine bottle. It was so revealing of his lifestyle. More importantly, the man can cook. We were entertained with a cute ass cheese plate for an appetizer, sausage and brussell sprouts, and a salad that we had all made with love. Fresh from the herb garden on his rooftop. We spent a lot of our time out there – shucking corn, cutting tomatoes, and trying to differentiate between this green leaf and the other. “This one is rosemary … or sage….or….kale? I don’t know put that in the salad.” Despite our uncertainty, the salad was scrumptious. Didn’t even need the drizzling of a balsamic vinegar dressing like I usually like.

My first night in Chicago can be summarized into one, simple statement: there is more to explore. The aching in my feet from that initial day would not compare to what would play through into the rest of my trip. I say I wanted to explore, huh? Well, I got my wish…

Stay tuned for Day 2.