Freddie and his wife, Joanne, see Dr. Richards to arrange a date to have the cancerous tumor cut out of his left nut, and Joanne embarrasses him by telling the doctor that he's very squeamish. Jack and Chris try to allay Freddie's fears. Divack announces to the staff that a friend got him a great deal on a luxury skybox to see the NJ Nets, et al, and it's open to everyone. Chris is infuriated when Divack starts babysitting him. Bridget gets Alex to do her a favor and take a client's sports agent friend--who wants to pitch an idea to the firm--off her hands by going with him to the Nets game tonight, as she has to tend to family business. While everyone is out enjoying the box, Jack becomes jealous when he sees Alex talking to the handsome agent, Grant Johnson. Alex falls for Grant, even if she has no interest in hearing him talk about sports. Over dinner, Gillian asks Chris about his time in the Navy, and caps off dinner by inviting him back to her place. A rude guy spills beer on Evan and then picks a fight with him, prompting one Mike Holden to come to Evan's defense, and demand that the guy offer up an apology. Freddie shares with Jack the time he thought he was going to bang a girl in the high school gym, only to end up the victim of a prank. Evan invites Mike out for some guy time to pay him back, while Grant invites Alex to dinner. Gillian and Chris do it, and Chris brags about that the next day. Evan seeks advice from the boys on how to do male bonding. Grant pitches his idea to the firm -- an expensive endorsement deal for an unknown basketball player -- but not even his claims that he's the next Michael Jordan make it a sure thing. Bridget drools when she finally meets Grant, and wishes she'd cancelled on her family instead. Tim warns Chris to break it off with his sister, who's irresponsible, but his words fall on deaf ears. When Divack seeks advice on whether or not to invest money in Grant's pick, Jack votes no, because he's jealous. Tim asks Donna out to dinner, hoping to get even with Chris. Evan's questioning his "relationship" with Mike freaks Freddie, Jack and Chris out. Chris stops by Gillian's place, thinking it'll just be the two of them, and is beside himself when she introduces him to her friend, Clay Hammond. Donna spends her date with Tim badmouthing Chris. Gillian tells Chris that Clay is loaded, and she got them together in hopes that he'd partner up with Clay. Bridget butts in on Alex's date with Grant. Evan, Jack and Freddie go out for drinks with Mike, and Mike and Freddie get into a tiff when Freddie takes a crack at Evan and Mike makes a ball joke--and not the sports kind. Freddie misinterprets every innocuous comment as a slam about his testicular turbulence, and nearly blows his stack when Mike naively lets it be known that Jack and Evan told him about the high school gym fiasco. Bridget tags along with Alex and Grant on their cab ride home. Jack digs up dirt on Grant -- an old company of his went bankrupt. Catherine advises him to see what Bridget knows, but Bridget pins the blame on Alex. He then goes to Alex, right before she puts her job on the line for Grant, but she brushes off the bankrupcy and flies off the handle when he says that Grant's pulled the wool over her eyes. Evan tells Freddie that Mike wants to take the gang out on him to patch things up, but Freddie thinks Mike's too much of a dork. Alex gets on Grant's bad side by confronting him about his dead company. She returns the favor by killing the deal, claiming that she needs more time to scrutinize it. When he erupts, she accuses him of trying to take advantage of her -- a move which allows Bridget to swoop in and steal him away once and for all. Donna apologizes to Tim for spending their entire date talking about Chris, and promises him another date to make it up to him. Gillian and Clay surprise Chris at work to tell him to quit his job, because they've got $50 million ready to be invested. Rather than thank Jack for saving her butt, Alex rudely tells him to keep his advice to himself. Evan takes his friends' words to heart, and breaks things off with Mike, who doesn't take it well. Joanne blindfolds Freddie at work, takes him home, and treats him to a romantic candlelight encounter -- in his high school gym.