Chicago, United States
Neil, 44
English Teacher
see his Chicago city guide

a bit about Neil

What do you do and why do you do it?

I'm a high school English teacher at one of the city's selective enrollment high schools. When I was really young and growing up in Kansas, I wanted to be a cowboy; I wanted to be the Lone Ranger. That dream died sometime after I started school. For a long time afterwards, I don't think I really knew what I wanted to do. I ended up teaching because it had been in my mind for a while after college. I was always good at school, and it can be really inspiring working with younger people. I like the feeling that I'm ultimately helping make a positive difference in the world.

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

To be honest, I can't really say that I've ever had a terrible job. They were all things that I needed at the time, and I guess I've learned to take something good out of all those experiences.

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

I grew up in small town Kansas, and I always wanted to get out. For college, I ended up in Baltimore. I went and lived in New York, which had been a dream of mine since middle school, after college. I ended up in Chicago because of family and, again, school. I guess it's become home to me; I've been here for 18 years now. I have to live in a city, and Chicago has become really comfortable to me.

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

Gold Coast. It's nice and quiet and comfortable. Public transportation options are aplenty. Close to downtown. It's just a little boring, but I'm okay with living in a boring neighborhood. I'm not in a place in my life where I need the party to be right outside my door all the time.

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

I tend to not discriminate in terms of genre. If it's good, if I enjoy it, then I'll listen to it. I tend to be more of an album person than a singles person: if you can't put together an entire album worth listening to, then I'm not going to be thinking much of you. I'll say that lately I've been really enjoying the new Slowdive album. It's gorgeous. They've matured so beautifully, and I feel so lucky to get to hear new music like this now.

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

Well, it really depends on what I want from the playlist: do I want to wallow in self pity or do I want catharsis? Generally, I'd probably want some soothing, dreamy stuff like Slowdive and Beach House and Panda Bear, maybe some How to Dress Well or James Blake, some poppy stuff like Robyn, and I can always find a way and a reason to work in New Order.

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

Of all time? Damn. I have no idea. I will say, however, that I've been totally into spy and conspiracy drama recently, like The Americans and Homeland. I loved 24 back when it was airing. And judge me if you like, but I find it highly entertaining to watch people turn on each other in reality shows like Survivor and Big Brother. God, Big Brother. Sometimes it's really hilarious to watch people slowly go crazy while they're trapped in a house for weeks on end and cut off from the outside world.

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

I have never used Tinder, and I'm not really interested in trying it out.

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

I don't really care.

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

I'm not sure who my hero is, but if I wanted to hang out with someone I really admired, I'd probably want to go to see a band with them. I wouldn't want to go see a big act at a big venue, though. It'd be cool if we could see a smaller, up-and-coming-act at Empty Bottle or Lincoln Hall.

Where do you buy those fabulous clothes of yours?

Generally, I'll shop anywhere. If I see a cool article of clothing at Target or GAP or Macy's or Neiman Marcus, I'll get it. For sneakers, though, St. Alfred has always been a great boutique. Mildblend has a really fantastic selection of denim. They have so many different brands that, until more recent years, haven't been that easy to find, particularly in Chicago.

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

Giordano's. Long line and too many tourists for what I don't even think is good Chicago-style pizza. No thanks.

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

Walk around and explore the parks and along the lake. These are pretty seasonal activities, and I can't always find time for them when the season is right.

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

This is so boring, but a really easy night out for me is to dinner and a movie or a concert. For movies, one of my standbys is Century Centre Cinema. I've experienced some really amazing films there, particularly in theater seven. I always have a very strong reaction to whatever is playing in theater seven, either positive (like In the Mood for Love or Before Sunset or Requiem for a Dream) or negative (Dancer in the Dark).

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

I always seem to end up at Little Goat when I'm celebrating something. It is an easy go-to spot. Diner-style food is very comforting to me, and Stephanie Izard does it well. I have yet to find something on the menu that I don't enjoy or that I don't want to try.

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

The CTA. I used to have a car, but I hated dealing with it and ended up getting rid of it. I love using public transportation in cities all over the world. I think it's a really cool way to get a feel for the city.

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

It doesn't matter how you do it--and there are a number of ways to do it--but the only thing I think that visitors should make sure to do is appreciate the skyline. You can do it from a cruise on the lake, a river tour, while walking along the beach--the list goes on and on. My favorite way to check it out is while checking out a band during Lollapalooza.

What are the Chicago spots tourists should run from screaming?

Taste of Chicago: It's so hot and crowded that your face will end up as greasy as the food you ingest while you're there.

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

Dinner and a show at one of the city's smaller clubs, like Empty Bottle or Lincoln Hall or Metro or The Vic. And then maybe a late night walk along the lake.

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

Berlin. It is everything I want. Super cool. Affordable. Fantastic nightlife. Great food. People are awesome. If I won the lottery, I'd totally buy myself a place there and spend summers and holidays there. Of course, I have to start buying lottery tickets in order for that to happen, and I know I won't bother, so it won't happen. But it's a nice thing to think about.