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 the patronizing is a common occurrence, it’s your turn to explain and teach him how to talk to you with more respect.
When it comes to managing your time between friends to keep everybody happy, realize that’s unrealistic to accomplish on your own. Your friends need to be good sports, too.
You don’t need bars. You just need good social atmospheres that fit your personality.
Being the best you can in a lower-profile, supporting role can still be fulfilling.
A simple hello can help people — whether you know them or not — through stressful, dark and frustrating times.
If you feel a connection, drop a hint that you’re interested. Leave no room for doubt you’re open to seeing them again. But also be ready for the possibility it won’t be mutual.
When financial advice doesn’t fully fit into our own circumstances, it’s up to us to fill in the blanks by learning from every personal mistake and success.
Feeling stuck in a comfort-over-fashion limbo? A stylish Chicago young woman talks about what motivates her to dress nice against chilly odds.
If we can move on from toxic friends, relationships and workplaces, why does family get a pass?