• Tess shows up at Adam’s jazzercise class to try to convince him how great they’d be together. But Adam is very adamant about that fact that he refuses to have a relationship with a married woman.
• Wanting to prove that he’s serious about her and not about to hurt her again, Nathan proposes marriage to Jenna, but she says no.
• Needing advice, Jenna calls Kenneth who’s at the movies with Elizabeth. Elizabeth advises Jenna to follow her heart, that if Jenna has doubts about Nathan, then maybe she should trust her instincts.
• Elizabeth and Kenneth return to her place which brings back memories of when they used to be together ~ high school sweethearts, being engaged and planning for the wedding, and the day Shari, someone Kenneth had met briefly in college, flew to Seattle to visit him unexpectedly.
• Jenna calls Tess for advice, but Tess refuses to speak to her. Tess still believes that Jenna was the one who told Adam Tess was married and ruined her chances of hooking up with him.
• With no one to talk to, Jenna tries to sort out her own feelings and remembers her high school crush on Nathan. Dateless for his senior prom, Jenna tries to cheer Nathan up by helping him figure out who he can take. Desperately hoping that he’ll choose her, Jenna is crushed when Nathan treats her as nothing more than Kenneth’s little sister and asks someone else to the prom instead. After being rejected by Nathan as a teenager, Jenna bumps into Colin in passing.
• Tess tries to figure out why she married Zane in the first place and flashes back to their wedding day. Having picked up two strange guys (one for each of them) at Neighbors the night before, they both oversleep and almost miss their wedding appointment at the Courthouse. With the two strangers as witnesses, Tess and Zane get married so that Zane can get his company promotion and make his parents happy and so that Tess can shock her parents with the fact that she married a gay guy.
• Still depressed that Kenneth’s been hanging out with Elizabeth, Shari mopes around her house. Nathan drops by to cheer Shari up and to try to forget his own problems with Jenna. Shari confides in him that she knew Kenneth was the one from the first time she saw him in college. She had been engaged to Kenneth’s classmate Andrew at the time. But when Andrew dumped her for someone else, she had flown directly to Seattle to pursue Kenneth. She seduced Kenneth away from Elizabeth and married him.
• Remembering how Kenneth had dumped her for Shari, Elizabeth doesn’t know if she should continue hanging out with Kenneth and risk having her heart broken again. She wonders what might have happened if she had followed Tess’ advice from before and tried to win Kenneth back from Shari using food and sex.
• Shari wonders what would have happened if she had gone after Kenneth when she had first met him – before he had gotten engaged to Elizabeth.
• Jenna wonders what might have happened if she had gone to Nathan’s senior prom.
• Tess wonders what might have happened if she hadn’t married a gay guy?
• They each have a “What if . . . ?” moment and fantasize about what their lives would be like if they had made different choices before.
• Shari would have gotten engaged to Kenneth in Boston. Elizabeth would have lost her virginity, but would have won Kenneth back from Shari. But they both realize that they still would have lost Kenneth anyway. If Shari had gotten engaged to him first in college, he would have always wondered if he should have gone back to Elizabeth in Seattle. If Elizabeth had won him away from Shari, he would have always wondered what would have happened if he had stayed with Shari.
• Nathan shows up in Shari’s fantasy and she realizes how lucky she is to have him for a friend.
• George shows up in Elizabeth’s fantasy and she realizes how lucky she is to have him for a friend.
• Tess imagines that if she had run out on her wedding to Zane, he would have so concerned that he would have done anything to make her happy, even if it meant having sex with her. But she realizes that she doesn’t want to ruin their friendship by making him be something he’s not.
• Jenna fantasizes about going to Nathan’s prom and realizes that maybe he’s never seen her for who she really is because she’s Chinese American and he’s white.
• Tess asks Zane for a divorce.
• Elizabeth tells Kenneth that she can’t hang out with him anymore as long as he’s still married to Shari and kisses him good-bye.
• Shari decides to go to Elizabeth’s apartment to confront her once and for all, only to see Elizabeth and Kenneth kissing.
• Jenna tries to explain to Colin that he’s the one that she loves, but he’s too hurt by what happened to take her back.
• Refusing to be dumped again, Shari asks Kenneth for a divorce before he can explain that nothing happened between him and Elizabeth.
• Elizabeth calls George to let him know she’s thinking about him.
• Jenna convinces Tess to meet her at the Barca so they can clear the air between them. At the Barca, Adam shows up and asks if he can call Jenna sometime. Tess shows up before Jenna can answer and not knowing what to do, Jenna tells Adam to hide, as she tries to patch things up with Tess.