Patti is skeptical about her first client Michael Leslie, who is successful in business, close to his family, a talented musician and, to top it off, a hopeless romantic. Michael has never been married and at the age of 58, he focuses on dating women in their 20s and 30s because he wants kids. Can Patti talk some sense into this guy and make him realize his priorities are out of order?

Patti is excited when she finds out her second millionaire is retired NFL star, turned ESPN-commentator Marcellus Wiley. Marcellus has a lot going for him including an Ivy League education. However, Patti quickly realizes that all those hours logged at work have put a toll on his relationships. She needs to teach Marcellus to be himself and keep his interviewing skills on the playing field, not in the dating field.