On a business trip together, Connor McCaffery did something that made Caitlin Clark extremely excited.

Caitlin Clark Celebrates Second Anniversary with Boyfriend Connor McCaffery

During a recent business trip that took them away from the WNBA spotlight and into more formal settings, Caitlin Clark and Connor McCaffery had fans buzzing—not because of basketball, but because of one unforgettable moment.

As reported by several onlookers who happened to be staying at the same upscale hotel in Chicago, the former Iowa Hawkeyes stars, now transitioning into professional life—Caitlin with the Indiana Fever and Connor as a team assistant—shared a moment that had even the staff smiling. But what did Connor McCaffery actually do to make Caitlin Clark light up like a firework?

It happened during a scheduled networking dinner with sports executives and potential endorsement partners. As the two arrived together—both dressed to the nines—Connor paused before entering the room, reached into his blazer, and pulled out a small black box.

Initial gasps turned into whispers as Caitlin, clearly surprised, smiled widely and looked momentarily stunned. But no, it wasn’t a proposal. Instead, Connor had custom-designed a pendant necklace featuring the coordinates of their alma mater’s basketball court—Carver-Hawkeye Arena. The necklace also included a tiny, engraved gold basketball with the date of Caitlin’s record-breaking game.

Witnesses say Clark’s reaction was priceless. She reportedly laughed, teared up a little, and immediately hugged Connor in front of everyone, saying, “This means more than you know.”

The gesture wasn’t about romance—it was about shared history, mutual respect, and a recognition of everything they’d been through on their parallel journeys. Connor later explained to someone at the dinner that he wanted to remind Caitlin that even though her world is exploding with attention, endorsements, and national pressure, her roots and their bond still matter.

Social media exploded within hours of the story getting leaked. Fans flooded comment sections with speculation—some cheering for a romantic angle, others praising the deep friendship. One fan wrote, “That’s how you show someone they’re seen. Connor is the real MVP here.”

In an age of performative gestures and clout-chasing moments, this was something else entirely. Caitlin’s genuine emotional response showed just how meaningful a thoughtful, personal gesture can be—even in a world that rarely slows down.