Peggy takes a paper out of the typewriter and starts to scrub an error, but knocks something to the floor in the process and then rips her skirt reaching over for it, causing her to look freaked out. If only Pete had ripped her skirt last time, she might have been carrying a spare.
In the break room, Lois and the switchboard girl with the glasses are telling Joan how boring their job is; Joan is surprised, thinking all the gossip would be completely salacious, but Lois replies: "They told me it would happen. But the truth is, you really just stop listening." Sounds like someone's no longer enamored with a certain well-dressed closeted Italian mama's boy. Peggy enters, having tied a sweater around her waist to cover the rip; hilariously, all three women look down as she passes, and if only they were copywriters, I think we would have just witnessed the genesis of the term "junk in the trunk." But actually, it's the sweater that's giving them pause, because after the switchboard girls leave, Joan basically asks if Peggy is using the sweater to hide certain monthly issues. Peggy confesses the news about the rip, and after ascertaining that it's too big to do a quick needle-and-thread fix, Joan nicely says she's got a spare outfit Peggy can borrow. That's generous of her, but do you really think it's appropriate for Peggy to finish out the day dressed as a naughty nurse?
Roger (...been a while, hasn't it) enters Don's office, golf bag over his shoulder but wearing a suit; Don comments on the incongruity, but Roger gets down to brass tacks, saying he's lost men like Don before, most likely due to his "unexpressed confidence." He tells Don he's one in a million, and adds that the bonus from Bertram was designed to protect against offers like the one from McCann. Also, he saw the clubs being delivered and thought they were for him, and nervously (for him) asks what Hobart offered. Don: "Bigger." There's that succinctness we all know and love. He goes on about the big clients, mentioning Pan Am specifically, prompting Roger to tell him that the lifestyle Hobart is promising isn't anywhere near as glamorous as he thinks. And he doesn't even know about the whole Catch Me If You Can thing. Roger confesses that he thought about leaving once, but realized it was a more daunting prospect that he originally thought, and he didn't want to entertain the possibility of failure. He asks Don if he really wants to start over, but Don tells him he hasn't made up his mind. Roger says he's taking Don's decision very personally, which I guess makes sense if he's thinking the pass he made at Betty might factor into it. Don says it's just business, and Roger, seeming almost hurt, parries, "Is it?" He leaves, and Don looks bemused.