Kris, another old friend from college, was not originally intended to be a date. I always thought he was cute, but when we first met, he was honestly way too young for me! Still, I always noticed a spark of joy emanating from him, such positivity, energy around exploration. Even through the dark years of......

In a rush to scarf a quick meal before going out on Tuesday, I found an Italian restaurant willing to rush a pizza order (take-away only). I ordered this along with an Aperol spritz, took my drink, found an unserviced oversized table occupied by one young boy, and sat on the edge of the bench.......

Dora was invited by Adam the very next day to dinner with some friends at a fancy “Munich-like” stylish restaurant. She was lukewarm on him, and we both knew we’d be exhausted from a crazy week, but it might be good for serendipity. Given our challenge, these were opportunities to say yes to. (This was......

This unexpected date arose the night before our challenge began, but I wanted to record it. This date encapsulates a lot of the challenge’s purpose for me: learning to discern right decisions and instincts, being braver in revealing how I feel, correctly identifying interest/availability (this is definitely not my strength!), and not rejecting potential interests......