Warren Feldman/Showtime
Ariana Bacle
August 03, 2015 AT 12:56 AM EDT

When it comes to winning friends and influencing people — emphasis on the “winning friends” part — we all know Bill Masters isn’t the most skilled. He’s constantly scowling; he doesn’t even try to be friendly most (okay, all) of the time. But in this episode, Bill is turning over a new leaf — or at least making an effort to.

While spending a probably ridiculous amount of time lurking in a bookstore to see how copies of the book are selling, he picks up a copy of Dale Carnegie’s now-classic, How to Win Friends and Influence People, and begins reading. Not for too long though: He eventually confronts one of the employees angrily, asking why Human Sexuality is tucked away now when they were displayed openly in the front window just months ago. As it turns out, people aren’t so comfortable picking up a copy of Human Sexuality — a feeling comparable to what the more shy among us must have felt buying, say, 50 Shades of Grey at the local Barnes & Noble — and have been instead calling ahead and then picking up the book.

The employee isn’t too happy with Bill after this unpleasant interaction though and sends him on his way — not before Bill buys that copy of How to Win Friends though, a book that will play into the rest of the (occasionally hilarious) episode.

Before we get to the humor though, let’s go over some of the drama: First of all, Henry’s over in Vietnam and writing home about feeling sick. He’s nauseated, he’s sweating, he’s got a fever — and Virginia is worried as hell. She expresses this to Bill, who is unsurprisingly unsympathetic, especially because he wants them to go on a book tour so they can sell more copies of their book and, as a result, get a second edition out. Anyone who is familiar with WebMD — and anyone who’s familiar with a hypochondriac obsessed with WebMD — will recognize their interaction: Virginia lists Henry’s symptoms and immediately assumes it’s malaria, whereas Bill matter-of-factly reminds her that his symptoms are broad, impossible to accurately diagnose via one letter, and… likely just indications of a typically harmless stomach bug.

Although Bill’s reaction is relatively rational, it’s not comforting to Virginia. Daniel Logan, however, is much better at comforting the concerned mom: When she tells him about the letter, he recalls his own experience getting dengue fever and malaria while he was in the war and then takes a look at Henry’s symptoms. Unlike Bill, he doesn’t dismiss Virginia’s suspicions that it could be malaria — instead he notes that if it is malaria, that could be enough to get Henry out of there on medical discharge. He’ll put in a word with the military, he says. And here likely begins Daniel’s attempt to woo Virginia.

Bill’s trying too, though. He learned that an important law for winning countless friends is to “always make the other person feel important.” So he heads to the store, picks up a fur coat, and gifts it to Virginia as a “token of my appreciation of you.” She’s surprised, both because giving gifts and baring emotions isn’t exactly Bill’s thing, but also because he is smiling. Or, to be fair, forcing a smile. Watching the usually stern Bill try out a grin is one of the show’s funnier moments — as well as one of its sweeter ones: Bill is trying so, so hard to be better, and the way the smile looks so comically out-of-place on his face shows just how difficult it is for him to change.

Giving an important woman a fur coat is one of Bill’s old tricks though. Libby goes in to see Barton and make sure she’s not going to die of an aneurysm anytime soon (their neighbor’s abrupt decline in health is making both Libby and her young daughter paranoid that she’s next), and ends up discovering the fur coat Bill gave to Virginia. Turns out that years and years ago, Bill also gave Libby a fur coat as a token of appreciation for helping him in his work — but he doesn’t even remember that. According to him, he celebrated by taking Libby out to dinner and buying the most expensive bottle of champagne. Not smooth, Bill. Not smooth.

Hearing about how at one point though Bill valued Libby enough to gift her with something extravagant though is enlightening: It’s often extremely hard to imagine the two of them ever being happy together since they are so stiff and separated now — and have been since basically the beginning of the series. How did they even end up exchanging rings at the altar? I often ask myself when I watch the two of them together. But moments like the one in this episode where Libby reminds Bill of the time he called her “instrumental” in helping him win a coveted job remind us — however briefly — that they one time had a very different relationship, one much like the one he somewhat has with Virginia now.

NEXT: Margaret and Barton, together again — kind of.

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