Chicago, United States
David, 36
see his Chicago city guide

a bit about David

What do you do and why do you do it?

I am an attorney and I do it because I like helping people. It sounds cliche and it is, but it is the truth. I work with a lot of small business owners to help them navigate the legal considerations of their business and help them achieve their goals. Most of my clients are pouring their heart and soul into their business, and it is amazing to be a part of that type of passion.

What’s the worst job you’ve ever had and why was it so effing bad?

My worst job was my first job. I worked at a small Italian restaurant as a cook. It was terrible because as a cook it is near impossible to make everyone happy. All the food has to be timed just right so it does not come out too early or too late. If you do make a mistake it sets off everyone and everything. The job did give me an immense appreciation for the food service industry and a lot of respect for those cooks that can make it all work.

Were you born and raised in Chicago? If not, where did you grow up and what brought you to Chicago?

I grew up in Michigan, but moved away right after high school and lived on the East Coast and overseas for a decade before moving to Chicago. I moved to Chicago mostly because I missed Lake Michigan and to be closer to family. I would certainly not have done it if Chicago was not a world class city. Seriously though, Lake Michigan is awesome.

What’s your current hood in Chicago and what’s the best/worst thing about it?

I live on the north side in Ravenswood. I am obviously quite partial but I think it is one of the best neighborhoods in a city of neighborhoods. It has great restaurants, great bars, public transit is easy, and our Alderman has helped push for a number of breweries to open up in the neighborhood. The one draw back, is that diversity could be higher. It is certainly not as lily white as some neighborhoods, but eschews more toward that than not.

What kind of music do you listen to and what kind of music do you absolutely HATE?

I enjoy music, but I am certainly not a fanatic about it. If left to my own devices I listen to a healthy mix of punk, reggae, classic rock, and 90' to early 00's hip-hop. In reality I listen to what my wife wants. Hate might be too strong of a word, but I have never been a fan of most Country music.

You’re broken hearted - what tracks does your heartbreak playlist consist of?

My broken hearted playlist would likely be all 80's new wave. Nothing says emotional wreak like synths and black hair dye.

Name the best TV shows of all time, and what makes them so good?

There are epic TV shows like the Wire, Mad Men, and Game of Thrones that suck you in to new world and spit you back out transformed. Those shows are probably the best by most metrics, but I have a soft spot for comedies where the characters are people behaving badly. This is a favorite comedy trope but my favorites are shows like Arrested Development and Its Always Sunny in Philadelphia. They took it to a new level and always leave me laughing.

Name some spots in Chicago that are good for a Tinder date.

I have never been on a Tinder date so I have no idea. But if I was taking someone on a first date I would recommend a museum followed by dinner. You can find something for just about anyone's artistic or cultural interest at the Art Institute of Chicago. That should give you plenty to talk about at dinner at Duck Duck Goat. Duck Duck Goat just low key enough to seem like you are not trying too hard, but unique and adventurous enough to be memorable.

Which public figure would you want to see “roasted”? (every public figure is fair game).

In this political environment there are too many figures to name, but they might not take it well. A "roast" is best when the "roastee" takes it well and is in on the jokes. With that in mind I would love to see Lauren Michaels of SNL roasted. He pokes a little fun of himself on the show, but still projects a very steady image. A roast might break down that image a little bit and give us a better idea about the man who runs SNL.

Who’s your hero and where in Chicago would you take them out for a serious hang?

I am cheating here and using a fictional character. My hero is MacGyver, and for a serious hang we would go watch a Blackhawks game at the United Center. Both MacGyver and I are huge hockey fans so it would be great to talk about the game and life while drinking a couple overpriced beers in the stands.

Where do you buy those fabulous clothes of yours?

I am an equal opportunity shopper, and rarely am I accused of having fabulous clothes. I buy clothes wherever I find something I like that does not cost an arm and a leg. Because of this my wife often takes me to the Fashion Outlets in Rosemont to get some nice clothes at a decent price.

What’s the area/ spot in town you’ll never be caught dead in?

Unless you are doing some serious day drinking before a Cubs game, I would never go to Wrigleyville. It is by far my least favorite place to go out in Chicago.

What’s the thing you LOVE to do in your city that you never get to do?

The Field Museum. I love museums generally and the Field Museum is a great mix of the classic museum experience from my childhood and more modern interactive museum experiences. The stuffed animal dioramas are classic and the Maori meeting house is a fantastic escape from the everyday. I rarely ever make it though as the Field museum is not as convenient as the Art Institute to get to. when visitors come I always push for a visit to the Field Museum for my own selfish reasons.

Where do you go in Chicago for a casual night out?

A casual night out with my wife or a couple friends normally involves dinner and some drinks at a neighborhood bar. I am lucky to have a fantastic bar called Fountainhead in my neighborhood so I often push for that. Where ever we go it is almost mandatory that they place have a good beer selection.

Where would you go in Chicago to celebrate some freaking good news?

My ideal place is Bavette's. It is a better version of the classic Chicago Steak House. It is nice enough that you feel like you are really celebrating, but not so nice/expensive that you feel as much pain in your pocketbook the next day. Plus the steak is fantastic, and nothing says celebration like a beautiful hunk of beef.

What’s your choice of transportation in Chicago and why?

The "EL" for sure. It takes you most places you want to go, quickly, cheaply, efficiently, and most importantly you are not responsible for driving. It means that you get a chance to read, catch up on the news, or have that extra beer with your friends all while being whisked to your destination. As an added bonus there is always good people watching.

What are the Chicago spots a first-time visitor can’t miss?

There are very few can't miss items. Rather than some cities with one main attraction, the main attraction of Chicago is the city itself. By that I mean the amazing architecture downtown, Lake Michigan, and all of the unique little neighborhoods. The closest thing to a can't miss is a view of the downtown from the river. While you can get this by just walking around, the best way is to take an architecture cruise. They are popular, but with good reason. I always like to book through the Chicago Architecture Foundation as they seem to have the best guides.

What are the Chicago spots tourists should run from screaming?

There are not a ton of truly terrible tourists spots. Navy Pier is certainly overrated, and few Chicagoans go there with any regularity, but even there you are on a pier in Lake Michigan with some beautiful views of the city. I would run away screaming from eating at most tourists spots. Even making it a few blocks away can make a big difference.

Tomorrow’s your last day in Chicago. How do you spend it?

I would start the day bright and early with a bike ride along the lake shore path to the Art Institute. I would then grab a hot dog and head to the beach for the afternoon. After that I am heading to one of my favorite restaurants, maybe Bavette's, for some great food and drinks.

What’s your favorite vacation city in the world and why?

London. It is an amazing city with fantastic restaurants, bars, and shopping. What sets it apart is that on top of all that it is oozing with history. You can hardly go a block with out running into a historic site. This mix of old and new in a global city is what makes London so amazing to visit.

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