Each episode, real people mark a major milestone, their 40th birthday, in amazing ways. Derrick, a former NFL player, sets out to prove he can still compete against the best. Lisa, a model-turned-mom, throws an extravagant Beverly Hills bash full of surprises and family drama, but will she finally embrace her age? Brian, a former thrill seeker who is now wheelchair-bound, aspires to skydive and ride a horse again. Rita, an Italian-American woman whose family never fit in growing up in rural Utah, heads to Italy to trace her roots. Tonya, in the midst of a divorce, had to cancel her plans for a Jamaican birthday trip. Can her friends pull together and make her wishes come true? DeeAnn lost her fiancé seven years ago, but she is now moving on. Will an 18th-century-themed masquerade ball and finding Prince Charming do the trick?