The fifth-season opener marks Steve's impending 40th birthday as he laments getting older without achieving many of his goals, including a motorcycle tour of the country. Meanwhile, during the summer vacation, Regina meets and begins dating a professional basketball player on a trip to the islands, and the relationship may lead to something even deeper. But the big news this episode is that Lovita discovers that all the queasiness she's been experiencing might be because she is pregnant. - - -
At the start of another school year, Steve is about to celebrate his 40th birthday. After assigning his students the task of listing their life's goals, Steve finds a similar list he prepared 20 years earlier, only to discover he has achieved little of what he wanted. Meanwhile, as Steve learns Regina is dating multi-millionaire basketball star Jordan Maddux, a pregnancy test indicates Lovita and Cedric are going to have a baby. Steve decides to turn 40 while on a cross-country motorcycle trip
