Fun fact: for a Popularity/ Family sim, Caleb's private life was kind of terrible. Cleo is his oldest daughter. He married her mother, Taylor Wooten (another teenage sweetheart) very young. Taylor, unfortunately, cheated on him with Luis Carver (prior to his marriage with Maisie) during Tallulah's wedding party. He broke up with her as soon as little Cleo was born.
Caleb was pretty desperate for a new relationship and settled on Bernadette Redgrave (the cheerleader) even though they did not share a single bolt of chemistry. Nevertheless, they married and had twins, Billie and Dexter. Billie, as you know, married into the Musgrove clan.
Dexter (Popularity/Romance) also settled quite young, surprisingly so for a romance sim. However, his marriage is much more stable than his dad's. He and his wife Orla (Popularity/ Fortune) are quite successful in their respective careers and have two children, Elliot, who's currently away at college, and Fallon.
After a while, Caleb and Bernadette's marriage fell apart and both of them cheated on each other. Caleb with Zelda Foster of all sims, and Bernadette with James Trainor, a family sim she was much better matched with. After they caught each other, they broke up and Bernadette moved in with her new boyfriend.
However, when all of this happend, she was unknowingly pregnant by Caleb and their last son, Adam, was born shortly before her wedding to James. He carries the Regrave name. As a knowledge sim, he and his friend Edward Musgrove were the first sims to attend college. There he met Prof. Orange and had a short fling with her. He then fell in love with a dormie called Evelyn but never was that serious about her, rather focussing on his career after moving back to Barrel's End. She eventually caught him on a date with Isolde Oddell and ended things. To my surprise, he didn't choose either of those ladies in the end and instead settled down with his first crush, Prof. Orange. They recently welcomed their first child, Peregrine Redgrave.
Bernadette had a long and happy marriage with James, even adopting a distant relative of his, Malik. James died when Malik was a toddler and Bernadette followed a few years later. Malik was taken by social services (Bernadette's roommate, Acacia was out shopping when Bernadette died) and adopted by his sister Billie.
Caleb decided to give marriage one more try and proposed to his girlfriend Acacia Glover after reaching the elder stage. She, however, left him at the altar and moved out after a lot of fighting. Caleb eventually fixed things with his first wife Taylor and they lived together until his death, even though both of them restrained from wanting to marry each other.
