Ben Tolpin

A nude painting of Marshall gives Barney an idea for a portrait of his own, and Ted can’t quite bring himself to fire his former boss in spite of the man’s obnoxiousness.

Nancy gets promoted and takes on new responsibilities. Silas and Shane both start their new jobs. Doug recruits homeless people in an attempt to legitimize his scam charity, while Jill breaks some upsetting news to Andy.

Nancy meets Rabbi Dave’s friends during an awkward Shabbos dinner. Andy brings home a very special guest to meet the family. Silas prepares for his new business venture. Shane and Angela attempt to retrieve some stolen property. Meanwhile, Doug’s homeless group threatens to leave him if he doesn’t begin catering to their needs.

For her birthday, Maddie is given a Halloween-free party.

As we reach our early 20s and face the daunting challenges of real life, there are those who choose to embark on a career path and those who'd rather goof off with pals. And then, every so often, there's someone who sets out to do both. Set in Chicago, The Loop is the story of Sam (Bret Harrison), the youngest executive at the corporate headquarters of a major airline, and the first of his friends to get a real job. He must find a way to straddle his serious career and the serious social demands of his three roommates.