Joey secretly throws a party on the roof of his building for the "Days of Our Lives" cast and he reluctantly invites the rest of the gang, once they discover his plans. Meanwhile, Ross meets a new colleague, Charlie, and is instantly attracted to her, however, he feels intimidated once he learns about her accomplished ex-boyfriends. Also, everyone forgets to tell Chandler about the change of plans and he gets stuck at a theater play by himself.

Joey comes to Ross for advice on dating Charlie, since they don't share much of the same interests. Meanwhile, Chandler and Monica bump into Janice at a fertility clinic. Also, Rachel has a gift certificate for a massage at a fancy massage place which Phoebe doesn't want her to use, since she doesn't approve of big corporations.

Rachel and Phoebe take Joey's girlfriend Charlie shopping, where she overhears the two of them gossiping about Joey. Meanwhile, Ross gives a presentation to a fellow professor in the hopes of getting the role of keynote speaker at the paleontology convention in Barbados. Also, Monica and Chandler consider alternate pregnancy options making some people really uncomfortable in the process.

The gang heads down to Barbados for the paleontology conference. While Ross and Charlie are excited about attending multiple seminars, the rest of the gang just want to enjoy their time on the beach but the rainy weather prevents them from doing so. Things, however, are far from boring - Phoebe discovers that she still has feelings for Mike even though she enjoys spending time with David, Rachel feels lonely and struggles to keep her feelings about Joey to herself, and Chandler is amused by Monica's hair.

After leaving Barbados, Joey and Ross both attempt to come clean to each other that they're dating Rachel and Charlie, however, various obstacles constantly get in their way. Meanwhile, Monica gets a new haircut much to Chandler's dismay and Phoebe finds out that Mike has another girlfriend.

After Ross finds out about Joey and Rachel's relationship, he invites Rachel, Joey and Charlie to a dinner party at his apartment, which ends up being really uncomfortable for everyone involved. Meanwhile, Monica and Chandler are overwhelmed by various adoption options and Phoebe suggests talking to a couple that has gone through the process. Unfortunately things go sideways when Chandler can't keep his big mouth shut. Also, Phoebe is visited by her brother, Frank Jr., who is desperate because he can no longer cope with his precocious triplets.

To help her younger sister, Amy, become a more responsible person, Rachel overrides Ross' strong protests and allows Amy to baby-sit Emma but soon regrets that decision. Meanwhile, Joey volunteers to write a recommendation letter for Monica and Chandler's adoption agency, however, he's concerned about not sounding smart. Also, Phoebe unknowingly thwarts Mike's "anniversary" surprise for her.

Ross has a chance to be selected by Dr. Benjamin Hobart for an esteemed paleontology grant. Unfortunately, Hobart happens to be Charlie's obsessed ex-boyfriend. Meanwhile, Phoebe tries to give a hideous painting she created to an extremely reluctant Monica and Rachel. Also, Joey is offended when Chandler lies about viewing Joey's bizarre audition tape reel.