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3. Tay in Chicago
48:44||Season 3, Ep. 3Meet Tay, a 32-year-old Edgewater resident who—about a year ago—wasbarely getting out of bed. She was going through a hard time, got thehelp she needed, and when she started feeling like herself again, shewent after everything she'd been too depleted to pursue: line dancing,tabletop RPGs, musical theater, two podcasts, tarot cards, a growinglibrary of YA audiobooks, and the 20-Sided Tavern—which she proceededto see twenty-seven times. She counted. She is proud of this.
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2. Scout in Chicago
43:48||Season 3, Ep. 21. Maria in Chicago
01:19:29||Season 3, Ep. 1Maria is a 48-year-old native Chicagoan, born on the Southwest Side and still loyal to every neighborhood in this city. She’s a freelance copywriter and communications pro building her own LLC, a longtime Zumba devotee (Miami-level, which is next-level), an evening coloring book enthusiast, a devoted auntie, and the owner of a Malti-Poo she is genuinely obsessed with. She has already storyboarded the Costco meet. She has been patient long enough.14. Justin in Chicago
27:52||Season 2, Ep. 1413. Simone in Chicago
41:49||Season 2, Ep. 1312. Marc in Chicago
37:10||Season 2, Ep. 1211. Riley in Chicago
33:38||Season 2, Ep. 11Meet Riley, a Lincoln Park actuary who calculates risk for a living but isn't afraid to take the leap when it comes to love. On paper, he's the guy who's spent a decade measuring pension risk in Excel. In reality? He's the guy showing up to AA meetings, sponsoring people in recovery, and speaking at treatment centers about hope—all while crushing it with the Silly Pickles pickleball league on weekends.