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Jane and Jordan met while running their companies in a downtown Manhattan coworking space. One day, Jordan fell in love… and it wasn’t with Jane—it was Jane’s dog, Fox. When he saw Jane without Fox, he asked, “Where’s your dog?” That moment sparked a quick friendship. They bonded over entrepreneurship, a little tennis, and endless dating advice—a friendship in its truest, most authentic form.

In the summer of 2024, Jordan realized there was something more than friendship. One night at Common Ground in East Hampton, his best man Josh nudged him: “JB, do you want to be friends forever—or shoot your shot?” With a bit of courage, Jordan confessed his feelings. Jane, usually never at a loss for words, went completely mute—a rejection at its finest.

The next morning, Jordan thought, “As long as Jane is still my friend, that’s all that matters.” Jane scheduled dinner to discuss the moment. Jordan expected the ultimate friend-zone talk—but Jane suggested continuing the night at a nearby bar. To his surprise, she asked about his intentions, the kind of partner he wanted to be, and his vision for the future. Jordan aced the test. Jane leaned in, and… the rest is history.