Loosies (2011) on Netflix

Bobby Corelli, who still lives with his widowed mother Rita, has been a New York-based pickpocket for five years. He got into the business after his father died, leaving behind a $500,000 criminal gambling debt. Bobby does the work for Jax, who threatened to kill him and Rita if he didn't go into the business to pay off the debt. Rita does not know about the debt, the threat to their lives, or what Bobby does, she believing him to be a Wall Street stockbroker. Bobby still has $100,000 left to pay Jax. The police are after Bobby as one of his marks was Lieutenant Nick Sullivan, whose badge Bobby lifted, the badge which Bobby has since used to get himself out of one jam after another. Sullivan's boss, Captain Tom Edwards, has issued Sullivan a "do whatever you need to" directive in getting his badge back. Bobby is approached by Lucy Atwood, an aspiring photographer, part-time waitress and a one night stand he had three months ago, who tells him that she is pregnant with his child. Bobby goes through a range of emotions in dealing with the news, all he really knowing is that he wants to help Lucy, who is wary of who she now considers a deadbeat, not even knowing about his pickpocket life. Bobby contemplates giving up his pickpocket life for Lucy and the baby. Even if he does and Lucy agrees, it may not be as easy for either Jax or Sullivan to forget and forgive their past history with Bobby. Bobby may get a little unwitting help in the entire matter from Carl, Rita's new jeweler boyfriend.