An advice column where Chicago can ask questions on how to navigate life transitions, relationships, family, finance and more.

Hey Chicago,

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 columnist Ismael Pérez doesn’t have the answers, chances are another Chicagoan will.

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.

Tell us your story and Ismael will share his thoughts, tips, lessons learned and more in a weekly column.
If we can move on from toxic friends, relationships and workplaces, why does family get a pass?
The challenges of finding true love, or even authentic chemistry, with someone seems to get more difficult with each new generation. AI is presenting another obstacle.
Change doesn’t mean a friendship has to end. It can be an opportunity for the relationship to form a stronger bond.
I followed a reality TV star on Instagram, and it led me to the question: Are ghosts real? And how do we come to explain the unexplained?
If a person is invited somewhere, is it implied their significant other is welcome as well? It depends ...
A 92-year-old widow wrote about an issue people of any age can relate to — a desire for a companion, along with the insecurities that come with putting yourself out there.
In 1955, Eppie Lederer became the Sun-Times’ third “Ann Landers,” bringing the advice column national prominence. This is an advice column for today. Send in your questions.