Eligible In

Meet 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.

In this engaging conversation, Larry, a Chicagoan with a passion for ghost tours and cemetery history, shares his unique journey from a childhood spent exploring cemeteries to becoming a tour guide. He discusses his interests in history, personal growth, and the challenges of dating as someone deeply connected to the supernatural. The conversation also touches on his culinary adventures in Chicago, his New Year's resolutions, and his thoughts on love and relationships, all while maintaining a humorous and light-hearted tone.

In this engaging conversation, Anil Balram shares his experiences navigating the complexities of dating, fatherhood, and personal growth. He discusses his career in media production, his intentional approach to dating, and the importance of mindfulness and presence in relationships. Anil reflects on the lessons learned from his past marriage and how fatherhood has shaped his perspective on love and connection. He emphasizes the need for balance between parenting and dating, and his aspirations for a future relationship filled with shared experiences and mutual support.

Meet Torrie, who's casually designing the infrastructure for a mode of transportation that doesn't fully exist yet. While most of us are still dodging electric scooters on sidewalks, she's planning where to park the flying taxis.

Meet Garrett, a Chicago-based software professional who works with restaurants— which makes perfect sense considering he comes from a long line of restaurant owners. The hospitality industry isn't just his job; it's in his DNA.

In this conversation, Devin and Kate share humorous and relatable stories about their worst dating experiences, highlighting the awkwardness that often accompanies first dates. Kate recounts a particularly uncomfortable date where her companion's nervousness led to an unusual revelation about their past. The discussion emphasizes the pressures individuals feel during initial encounters and the importance of not taking these situations too seriously.