You will meet ten to fifteen people in about two hours, each for five minutes. What you wear matters less than you think and more than you would like – it is the one thing every single person at the table notices before you say a word. Here is the advice we give first-timers.
Dress for the venue, one notch up
Our downtown events run in cocktail lounges and hotel bars; suburban nights are usually a restaurant with a reserved room. Think “nice dinner out,” then add one deliberate touch: a jacket, a good watch, a pair of shoes you actually like. Nobody has ever regretted being slightly overdressed at a speed dating night. Plenty of people have regretted the hoodie.
Chicago winters are real
From November to March you will arrive in a parka and boots. That is fine – every venue has a coat check or a rack. The trick is what is underneath: a layer you can take off, and shoes you can change into or that survive slush. Do not let the weather talk you into the gym fleece.
Comfort wins over fashion
You will be sitting, standing, and moving to a new table every five minutes. Anything you keep adjusting – a tight collar, a strap, heels you cannot walk in – will show on your face. Wear the thing you feel good in, not the thing you bought for the occasion.
One detail people can ask about
A conversation starter you wear is worth more than a perfect outfit: a pin from a place you love, a team you follow, a piece you got somewhere with a story. Five minutes goes fast; give people an easy way in.
Ready to test it out? Browse our upcoming speed dating events in Chicago or read how speed dating works first.