Shopping for gifts to bestow upon Jack at his "surprise" birthday party, Grace has an actual surprise: a chance meeting with Sam -- guest star John Slattery! -- a contractor who worked on a house she decorated and, oh yeah, Will's estranged brother. See, Will and Sam have been estranged since Sam asked Will's opinion of Sam's girlfriend and Will told him, truthfully, that she was terrible...and then Sam said he was going to marry her. But now Sam is getting divorced, so Grace thinks the time is right to get the Truman boys back together, and that Jack's birthday party will be the perfect setting! She is wrong on both counts. Speaking of wrong: Jack is excited to celebrate his birthday until it turns out he hasn't quite nailed the simple math and didn't realize he was celebrating a bigger milestone than he thought. We discuss which Truman we'd like to keep around!Learn more about your ad choices. Visit megaphone.fm/adchoices