H.M. Pulham, Esq., aka Harry Pulham (Young), is a middle-aged businessman living in Boston. Some of his old Harvard buddies contact him about their 25th anniversary class reunion. At the same time, Harry gets a call from his old girlfriend, Marvin Myles (Lamarr). A good two decades ago Harry broke up with Marvin, a career woman in the advertising business, and settled down to a more conventional married life with wife Kay (Hussey). The marriage has gone stale, though, and Harry's reflective mood and the arrival of Marvin throws him into a full-blown mid-life crisis. A series of flashbacks then narrate Harry's life, his romance with Marvin, and how he came to marry Kay instead.
H.M. Pulham, Esq. was co-written by Vidor and his wife Elizabeth, based on a novel by John P. Marquand.
- Bittersweet Ending: Harry and Marvin decide not to rekindle their affair, saying "We can't go back." But Kay, who has finally realized that Harry is going through an emotional crisis, finds him outside the office and whisks him away on the impromptu road trip that he asked her to take.
- Call-Back: Late in the film, after Marvin's reappearance has upset his life, Harry goes on his trip to work, but in a considerably more agitated state—blowing off the squirrels in the park, angrily kicking off his shoes in the office.
- Establishing Character Moment: Harry is shown as a borderline obsessive-compulsive who counts his steps on the way to work and always takes the exact same number of peanuts to throw to the squirrels in the park.
- Framing Device: A request for Harry to write an autobiographical note for the class reunion leads Harry to reflect on his life.
- Flashback: Most of the film is a series of flashbacks showing Harry's life.
- Have a Gay Old Time: "Must be queer being in two places at once"
- Inner Monologue: Throughout the movie as Harry is thinking about his life.
- Literal Metaphor: Kay and Harry are going boating. She admits that she thought a man was going to sweep her away, only for him to dump her. Then she remembers Harry's breakup with Marvin and says "I guess we're both in the same boat." Harry looks down at the actual boat that they're actually in, chuckles, and says "Yes, well, we're in the same boat."
- Meet Cute: Harry meets Kay at a dancing school when they're children, when someone literally bumps him into her.
- Quitting to Get Married: Taken for granted, at least as far as Harry's concerned, and the reason he and Marvin break up. Harry wants to go back to Boston with Marvin as his society wife, while Marvin wants a career. The ending reveals that Marvin managed to find a husband who was OK with her being a high-powered executive. Harry's frown of displeasure as Marvin interrupts their reunion to take a business call helps him to be more content with his decisions.
- Serious Business: Harry's college buddy Bo-jo Brown weeps on the realization that a leg injury is going to keep him out of the football game against Yale.
- She's Got Legs: Marvin is introduced leaning over a desk in a skirt that shows off her shapely calves.
- Sleeping Single: On his honeymoon, no less. This was an Enforced Trope in 1941, of course, but here it's appropriate, suggesting that Harry has left an exciting life with Marvin for a duller one with Kay.
- Smoking Is Cool: When Harry sees Marvin again after 20 years she is looking very fashionable, smoking a cool cigarette holder.
- Title Drop: This is how Marvin identifies Harry when she calls his office.
- Tomboyish Name: Harry's girlfriend is named "Marvin". Possibly appropriate as Marvin is a career woman rather than a conventionally feminine wife-to-be.
- Viewers Are Morons: In-Universe. Harry says he doesn't get an ad. The designer of the ad suggests it's because Harry doesn't have any brains. Harry's boss leaves no doubt this trope is in effect."Do you suppose for the average person who sees this picture is going to have any brains? We're not trying to be intellectual, Ellsmere."