I still remember the crisp October morning I arrived in Chicago.
A Lyft picked me up at Midway Airport and dropped me in Ukrainian Village, where a handsome man with an athletic build was waiting on the steps of his home.
“I’m so happy you’re real,” I told him, secretly referring to his good looks but mostly thankful the attractive profile picture offering me a last-minute apartment deal wasn’t an online scam.
He laughed and helped carry my 50-pound bag to the second floor — the first time I experienced that famous Midwestern kindness. I needed it.
After I paid the first month’s rent, I was left with $80 to my name, sleeping on a camping cot my landlord kindly provided. I had moved from San Antonio and lost my security deposit because I lied to my landlord about not having a cat.
I was broke and alone but had made it to Chicago. After many failed negotiations in my 20s, I was able to convince the Chicago Sun-Times to give me a relocation allowance that would come with my first paycheck. So I knew my struggles were temporary and my new life in this city was going to get better soon.
That’s what most of my young adult life has been like — take chances, deal with the punches, learn as you go. Situations fellow Chicagoans might be familiar with and could use some advice about.
That’s why the Sun-Times is bringing back a personalized advice column for the city — and for our generation — called “Someone in Chicago.” It will be written by me.
Advice columns then and now
This newspaper has a history of building a rapport with readers. In September 1955, Eppie Lederer became the Sun-Times’ third and most famous writer using the “Ann Landers” pen name, bringing the advice column national prominence.
Readers leaned on Ann Landers in part to “blow off some steam,” as a reader from California put it in July 1986. A Chicago reader wrote in May 1986 asking for clarity on an issue they “never had the nerve to ask anyone for fear of revealing my ignorance.”
Someone in Chicago will offer a similar space on questions affecting us today.
As a columnist, I have been open about issues such as addiction, sex and growing up gay in a conservative, Catholic household. On a less serious note, I love flowers, bragging about thrift-store deals and making people laugh.
When taking advice, I’ve been receptive and open-minded. But I also can be hardheaded, someone who needs to hear a lesson three different ways to finally get it.
In giving advice, it doesn’t matter whether you are a confident stranger or a delusional friend, I do my best to deliver something that’s sometimes hard but necessary to hear: the truth. Maybe with a joke to soften the blow.
Someone in Chicago
This new advice column will be a place where Chicagoans — whether you’re a born-here, die-here lifer or a transplant like me — can ask questions on how to navigate life transitions, relationships, family, finance and more.
Are you getting anxious thinking your partner might propose too soon? Or worry your relationship isn’t going anywhere? Write in.
Having trouble with an older co-worker who doesn’t take you seriously? Vent with me.
Wondering about good places to meet new people? Ask Someone in Chicago.
If I don’t have the answers, chances are another Chicagoan will.
Advice columns started as a platform to advise about manners and maybe tips on planning a housewarming party. As passing generations developed more curiosity on social issues and wanted answers to questions they were afraid to ask, it became a place where you could feel heard while learning from others with valuable similarities or differences.
With this column — through every insecurity we overcome, gems we discover throughout our city, new passions we find within ourselves — you’ll leave feeling connected to someone in Chicago.
Write to “Someone in Chicago” at someoneinchicago@suntimes.com or fill out this form.
