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.
Avondale’s Anthony Corrado was building a following with his uninhibited comedy videos when he received an ominous diagnosis last year, but he decided sharing his reality with fans would keep the momentum going — and be “a good distraction.”
How comfortable a guest can get depends on the size of the party, their relationship with the host and the limits and boundaries the host establishes.
Moms benefit from knowing women who not only understand their struggles, but also have kids who get along with their own. I asked some mom friends of mine for advice on where and how to meet other parents.
If you’re losing your hair, here are useful lessons and realizations from an experienced and confident bald person.
A Chicago expert shares insights on how to handle a toddler’s ever-changing tastes.
Young entrepreneurs and supportive patrons can meet each other halfway on this. Here are some thoughts on how to do that.
Here are some tips for building a routine to calm anxieties about the start of a new workweek.
If the camera downstairs gives you a feeling of discomfort, go ahead and call for it to be removed.
The next time wedding drama comes up as you plan your wedding day, sit down with people you trust and see what you’re willing to compromise and what’s nonnegotiable.
To help you see into a woman’s mind, I asked three of my close friends what worked for them.
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