Fiona and Michael Westen were staking out Carla’s known post office box and, as usual, Fiona is completely absorbed with her own life thinking its smug to refuse her shift at watching the box. A secretary came to pick up the mail and they tailed her back to Carla’s office. Security guards were masquerading as handy-men so they called a pizza delivery to see if there was any security response – there was. Now to plan a break-in. Sam came for a visit with intel on the building and the idea of using a webcam for surveillance – that, and to show M his $8,000 watch which Veronica had given him for their "one-month-since-we-said-I-Love-You anniversary." Waiting at the loft when he got home was Trevor an ex-con with a problem. A cell mate had told him about a guy who had busted up his organization, so Trevor looked the guy up and now hoped M could help keep him out of trouble. The boss of his old gang, Timo, wanted him to be a get-away expeditor for a jewel heist in a “do-it-or-die” mode. M really made him beg but eventually after Trevor said that he’d "promised his son to stay clean," relented. M and Sam watched at the isolated boat-house while first-line picks for Timo's crew came in for some planning. There was: C.J. – con man and hustler; Gilbert Kessler – safe cracker; Kandi – the enforcer/muscle; and, Timo – the thief. M had Fiona try to get Gilbert busted for breaking his parole restrictions for drinking, which failed; so, Sam picked a fight with Gilbert and let Gilbert beat him up in front of police.
Unfortunately, taking out the safe-cracker didn't cause Timo to cancel the heist; so, M had Trevor introduce him as Joseph, a replacement safe-cracker. Back with Carla, M broke into the building across the street from Carla’s and set up a web-cam. Then, after analysis, Sam found that there was a weakness with their security: a distraction at shift change. Sam had his special dinner with Veronica that night and she asked him to marry her! He said "now there's a question" but didn't give her an immediate answer. Back with M, he practiced his safe-cracking skills and Fiona kept interrupting saying that "C-4 is the answer." Timo took M to audition by cracking a convenience store safe and threatened to kill Trevor if he didn't crack it. Timo gave M a cell phone that he had to answer "by the third ring, even if you are in the bathroom." M was able to manipulate the conversation enough to find out the specific kind of safe they were planning to crack and when it had been installed. Later, Trevor got the locations of the scatter points which he had to arrange getaway vehicles at. Sam revealed that Veronica had popped the question. Mikes advice: "Do you love her?" [She could be the one.] "Then say yes." [But it’s complicated.] "Then say no." [You’re a true friend Mike.]
They were able to find the location of where that specialized of safe was installed, then when they did surveillance of the hit site, they saw that C. J. was working an inside man. They realized that they couldn’t inform the owners of the impending heist without C.J. finding out. Back with Carla, Sam hired a boy to skateboard down the alley and create the diversion so M could sneak in. Almost at the door, Timo called, so M had to turn around and leave without going in. While waiting with Fiona at Timo's boat shack, Sam revealed that he couldn’t marry Veronica because it was "against the law – I'm sort of already married." At least he hadn’t gotten around to getting a divorce from someone he had married on a whim for a day in the ‘70s. Fiona advised him to tell Veronica the truth because everyone had skeleton's and she would understand.
M realized that Timo was starting the heist right then and the only thing M could do was to drop a note where Sam might be watching him do it. C.J. Let Timo's heating-maintenance truck in the jewelry warehouse, with them all hiding inside, and the heist began. Outside, Sam tripped the burglar alarm early so they had to abort the heist, but before they left M made sure that everyone saw him show Timo something on the inside of his bag. Sam flattened a tire on the car that Timo was supposed to escape in, so he didn’t show up back at the boat-house with the others. M told the others that he had really gotten the jewels and Fiona blew up the boathouse to make it look like Timo had double crossed them. M hit Trevor, to sell the effect, and said he was going to go kill Timo. Kandi said that she would take care of it for them and she did. Back with Carla's office another time, Fiona was stalling going with M until Sam appeared with his suitcases saying that he was moving back into the loft because Veronica had thrown him out -- thank you very much Fiona! When M got into Carla’s office he found that it was empty except that Carla had left a photo frame of him attempting his last break-in with a message about "day jobs getting in the way", a bottle of champagne, Mylar “congratulations” balloons and another crossword puzzle.