In the fifth-season opener, Amy (Shailene Woodley) and Ricky (Daren Kagasoff) run off as they contemplate eloping, and George (Mark Derwin) is the only person aware of their secret. Amy begins her senior year of high school and gives guidance to a new student, who's six months pregnant. Leo Boykewich is the father of Ben Boykewich, adoptive father of Chloe Boykewich, husband of Camille Boykewich, and grandfather of Mercy Boykewich. Leo Boykewich is one of the most wise characters in The Secret Life of the American Teenager. He even supported Ben's decision to marrying Amy since he met Ben's mother when they were in high school. In the second season, Leo begins to date a woman named Betty (who is the prostitute Tom had once hired). When the baby is stillborn, Leo tearfully breaks the news to Ben and Adrian's friends at the hospital and then later supports Ben's decision to get a divorce. In Season 4, Leo questions whether or not he wants to be married to Betty anymore when he suspects that his longtime assistant Camille is in love with him.

Even so, Leo decides to stick with the marriage because he believes that is the right thing to do. They get married in the fifth season and decide to take in a young girl who was the under-aged prostitute that Jack helped out. They actually wanted to get married at an even younger age, but Sarah's parents made them wait. When Leo talks to Ben about Camille quitting, Ben says that it's clearly because she is in love with him. Elsewhere, Ben (Ken Baumann) wrestles with guilt concerning a fire; and Adrian (Francia Raisa) prepares for college. He always has words of wisdom and is one of the first people to suspect Amy Juergens's pregnancy due to her huge appetite and nausea. It is later revealed that Betty was very upfront about her profession the first day she introduced herself to Leo because she was afraid of embarrassing him. He promises to hunt down her husband, who turns out to be dead and they get married in an elaborate ceremony.

He is upset when Ben and Adrian discover they are having a baby and tries to caution him from marrying Adrian just because she is pregnant.
When Ben is ambivalent about being married, Leo sternly tells him that he made the choice and he now has to make the best of it. They begin to date, and in early Season 5, Camille informs Leo that she would like to have a child with him.
While talking in the car on the way to dinner, Camille kisses Leo and the two of them are later seen together at graduation.

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