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Caleb became a father at a very young age when his then-girlfriend, Abigail, fell pregnant with their son, Nick. That relationship was not meant to be and they broke up when Nick was a child, splitting time with their son equally.

In 2013, Caleb met Cara, who was then working as a waitress and had dreams of attending medical school. She took a little convincing but the couple were soon dating. Two years later, they found themselves unexpectedly expecting a baby. This was followed quickly by a proposal from Caleb but unfortunately, that pregnancy ended in miscarriage.

Caleb and Cara decided to put the wedding off until Cara was closer to graduating from medical school and the wedding finally took place in 2017, five years after they'd first met. The wedding was almost immediately followed by Caleb and Cara conceiving their twins, Anthony and Veronica.

By the time the twins arrived, Caleb was growing disillusioned with his uninspiring job as a comic book penciller and started becoming interested in cooking. It was with Cara's encouragement that he finally entered the restaurant business in 2021. Just 8 years later, he opened his own catering business, Delizioso Catering, still operating in Sullivan.