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.

Riley got sober in June 2020, and he'll tell you plainly: it's the best thing that ever happened to him. Five years later, he's added yoga three times a week, golfing every summer weekend, and long lakefront rides with Mac, his five-year-old golden retriever. Side note: Riley's already plotting his second dog's name—Cheese, so they can be Mac and Cheese.

We talked about what five years of sobriety has actually taught him about himself, how to navigate the "wanna grab drinks?" first date when you don't drink, and the risk-reward game of dating from an actual actuary's perspective. Riley breaks down what emotional maturity looks like in a relationship, why he won't settle for less, and why vulnerability—not chemistry—is what makes a relationship last.

He's thoughtful, grounded, a little introverted but completely disarming. And he just wants someone who loves dogs, makes time pass without noticing, and is up for wherever the night takes them.

Do you know a woman in Chicago who's ready for someone this intentional?

If you know her, let's connect her with Riley. Details below 👇