27, Lake ViewReal-life roles: Assistant squash pro; afterschool program founder and board member
Starring in: Risky Business
Is squash the new basketball? “MetroSquash is really just a good afterschool program; the hook just happens to be squash,” O’Malley says of the program he incorporated in 2003 for public school students. The New York native picked up squash at a Connecticut boarding school before playing for Ohio’s Denison University. As for his protégés, recruited from two South Side schools with a third on tap: “We want to get them at a young age and have a positive impact. They can slack off [elsewhere], but if they commit to this program, we’re going to make sure they show up on time. There’s accountability.”
What’s your go-to homemade meal? Delivery.com.
Have you ever collected anything? Parking tickets and squash gear.
Worst advice you’ve been given? To go to Mexico for dinner from L.A. Apparently, taking rental cars across national lines is a federal offense; chalk that one up to inexperience. It was a very close call to spending time in a Mexican jail.
Do you have any tattoos? My family crest [depicting a wild boar] on my right arm.
What did you do on your best date? Suddenly, all of the bad ones are coming back. But it’s not about what you do but how you connect with the person.
In a dream world, who would you look like? Me. Part of maturing is getting comfortable with yourself. Write like? Barack Obama. Dance like? Myself. I’m not good, but I’ve got a lot of heart. Cook like? My mom. And sing like? My sister. It might not be good to say I want to sing like a girl, but she’s really witty and tells beautiful stories.
What do you do every day? Play squash, shower, drink coffee, check e-mail, talk on the phone, and think about what I can do better.
Favorite movie hero? Tom Hanks in Saving Private Ryan.
Most quotable movie line? “What you feel only matters to you. It’s what you do to the people you love. That’s what matters. That’s the only thing that counts”—Tom Wilkinson’s character to Zach Braff’s character in The Last Kiss.
Most recommended book? Whatever I’m reading at the time. I just started The Devil in the White City, and I’m reading The Audacity of Hope. I like to have two books going at a time. I’m not a speed reader but a mood reader.
Name one thing that’s overrated: Waking up early.
When you’re alone, who do you play air guitar to? Weezer.
What song will be played at your wedding? Van Morrison’s Crazy Love.
Fill in the blanks: Vacations are for getting away, not working.
You pull a Ferris Bueller and call in sick on a beautiful July day. What do you do? Sail. I love to sail, although I haven’t gotten into it in Chicago. And I’d get a massage. I still haven’t been to see any symphony or opera in Chicago, and I haven’t been to Japonais. So, I’d get up early and stay up late.
What Chicago neighborhoods have you lived in? Lake View, Lincoln Park, West Loop, and borderline Wrigleyville. I love where I am now. It’s close to the lake.
How long is too long to spend looking for a parking spot? If it’s more than 15 minutes, I start to get pretty “Oh, my God.”
Teacher’s pet or class clown? It went back and forth, depending on the teacher.
Childhood nickname? None. Conor’s tough to make a nickname out of.
What did you think you’d be when you grew up? Like my dad; he’s a lawyer.
Name one thing you have in your house from your childhood: This book my sister made me for my ninth grade graduation that covers my childhood. She updated it again after college.
And one embarrassing thing you hide when guests are coming over: Laundry that’s been piling up. I tuck it in the closet.
Describe the state of your closet: It’s all over my room. The shirts and suits are hung up; everything else is all over the place.
What’s your power outfit? I just bought a custom-made suit. It feels pretty good.
How much is too much to pay for jeans? I used to think that people who spent a lot of money on jeans were crazy, until I realized I wear them all the time. So, no more than $200.
What’s in your pockets right now? My wallet, a quarter, a dry-cleaning stub, and my cell phone.
Last time you jumped up and cheered? It was when I won a large bet, at a squash tournament of all places, against a good buddy of mine. Still waiting for the payout.
Last time you told a lie? I try not to, but there are always little white lies to get through society.
Last time you Googled yourself? Three or four weeks ago.
If you could give someone a talking-to, who would it be? George Bush.
What do you do when a server at a restaurant brings you a horrible dish? Gauge it. If it’s horrible, I made the bad selection.
Gutsiest thing you’ve ever done? Working on METROSquash. I wasn’t making any money, and I was going for eight months or a year on blind faith that it would work out. My parents were like, “What are you doing?”
What time is your alarm clock set for? Usually 8:15 a.m., but it varies during the week.
And how many times do you hit the snooze button? Too many.
Dive bar or nightclub? Dive bar.
Drinks before 5 p.m.: always, sometimes, never? When I’m not working, always.
What’s your remedy for a tough day? Certainly exercise, capped off with a beverage of choice. Lately that’s a Manhattan.
Fill in the blanks: I’d rather have a significant other who challenges me than who rolls over.
How do you show someone you’re not interested? Stop returning phone calls.
Where would you like to get engaged? Somewhere meaningful to the relationship.What makes someone a Chicagoan? A Chicagoan rides the el. No—braves the el.
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