How we met
Jeffrey and Caleb met at a donor recognition event hosted by a clinic in Indianapolis, where Jeffrey served on the board. Caleb had donated to the clinic and attended the event. What began as casual conversation quickly turned into something more meaningful when they discovered an unexpected connection: Jeffrey worked for a health insurance company overseeing the provider network, and Caleb was in the midst of struggling to secure a contract to join that very network.
When Caleb shared his frustration about the lack of support he had received, Jeffrey’s curiosity and problem-solving instincts immediately kicked in. He began asking detailed questions about who Caleb had spoken with and what had gone wrong. Caleb was a bit intimidated by Jeffrey’s directness, while Jeffrey was trying to understand the issue without overwhelming him—but that honest exchange became the foundation of their connection. Looking back, it’s almost the perfect representation of what makes their relationship so strong; Caleb being the caring partner who softens the edges, creating emotional safety and connection, while the Jeffrey focuses on direction and momentum. Each brings out the best in the other, forming a partnership built on mutual respect, balance, and trust.
From there, the two discovered they had a great deal in common. What started as an unlikely professional conversation grew into a genuine friendship, then a close bond, and eventually something more. Over time, that first unexpected meeting turned into a relationship neither of them could have anticipated—and one that changed both of their lives.
A excerpt from their first day together…
Jeffrey: “This is your out - you don’t have to go for a bike ride with me.”
Caleb (while anxiously sweating): “Why would I want an out? Oh, and my tire is flat”
The Proposal
Marriage had been a conversation for Jeffrey & Caleb for a while but the actual engagement wasn’t really considered. The two had discussed rings and knew what they wanted but hadn’t executed a plan. Before going on a vacation they planned, Jeffrey decided it was time to make it official and pop the question. With some help from friends (thank you to Mark, Ken, Keeley & Robbie) Jeffrey put up the Christmas tree at home to represent their upcoming trip to Palm Springs for Christmas and surprised Caleb with a proposal and the ring when he came home from spending the day at his mom’s house. After Caleb agreed to tolerate Jeffrey for eternity, the two celebrated by popping some champagne and toasting with the friends who helped set it up.