I Am the Prize (2020)

Laura and Martin have been friends since university but have never been romantically involved: she's always dating hot guys, and he gets shy around ladies he likes. One day, Laura decides that she is going to help Martin get a girlfriend before a party in six weeks time. She sets him up on some blind dates, but they don't go so well, so she decides to get him some 'professional help' to help him understand how to succeed with women: enter Sebastian, the sleaziest Dating Coach / Pick Up Artist this side of LA.