Synopsis/Details
Herman Winslow, relationship expert, tenured professor, best-selling author, therapist to the stars, is having trouble finishing his latest book called Adventures in Dating. There are 10 days remaining until the deadline, at which point, if he hasn’t completed the final chapter, the contract will be voided and he will have to give back the advance - which, of course, he no longer has. Herman lives with his aging father and his father’s much younger wife, in the backhouse of his childhood home. He is still getting over a break-up that occurred several years ago. His agent urges him to reenter the dating scene, suggesting that this might provide the creative inspiration necessary to complete the book, but Winslow’s heart is not into it - not until his friend Steve sets him up with a real knockout of a girl, whose name is Andrea.
In preparation for meeting her, Herman puts himself out there. He goes out for drinks with a group of his students, and gives himself a make-over. But the date with his dream girl falls flat, as she too is getting over a break-up, and is somewhat out of it. They reconnect and have a nice time at a photo-shoot, but when Herman catches her with her ex-boyfriend he departs in dismay. Nevertheless, his encounters with Andrea, although brief, reinstill the confidence necessary to break things off once and for all with his former flame. Meanwhile, his social life picks up. His father sets him up with his caregiver, Herman has an impromptu encounter with a pretty neighbor, and an encounter with a student that is misconstrued gets him dismissed from his teaching position. In the process Herman realizes that he doesn’t know as much about relationships as he once believed. His father passes away and Herman moves out. Steve tells Herman that Andrea turned down her ex-boyfriend and is interested in him, so he brings her flowers, and when she finds out he is without a home, she invites him to stay with her. To repay her for her kindness he offers his services as footman, helping around the house, and with her children.
Herman manages to finish his book only to learn that due to his dismissal the publishing contract has been canceled, and so he finds himself jobless, homeless, penniless, and wondering what to do with the rest of his life. Andrea to the rescue. She gets him out in the world, introduces him to friends, puts him in the public eye where he makes an impact, not by dispensing advice but by asking the right questions to reveal the answers in others. He does the podcast and talk show circuit before he gets his own show, with Andrea as his co-host. His agent calls offering to renew his publishing contract; Herman replies that he has left dispensing advice and giving answers behind him for a life of listening to others and asking the right questions.
