The Pick-up Artist

In this charming 1987 romantic comedy-drama, Molly Ringwald shines as Randy Jensen, a feisty museum tour guide who proves to be the perfect match for Robert Downey Jr.'s smooth-talking but ultimately hapless womanizer, Jack Jericho. When Jack falls for Randy, he must navigate his own demons and confront the dark underbelly of her family's past, including a mobster father and a debt that could ruin everything. As they navigate their whirlwind romance, Jack learns that sometimes it takes a little risk to find true love - but will he be brave enough to take a chance on Randy?