Cindy shows up at Mark's office that night in a little black dress. Mark asks what she wanted to tell him. Cindy chickens out, saying that she just wants to go out and have fun instead of talking. She says "please," and Mark says "sure," and they kiss. Richard walks in and then back out again.
At The Restaurant where all the characters go with their dates before they go to The Bar, Michael plays "Sweet Caroline" with the house band. The whole restaurant sings, just like they did during last season's finale, but this time, implausibly, it's not a hallucination. Ally rubs the napkin all over her gaping mouth. Go throw yourself into a pit, Ally.
Then we see Ally dancing with Jonathan in The Bar. Renee sings "Mr. Big Stuff." Ally voice-overs for several hours. Renee sings to them and then to Mark and Cindy, who are also dancing there, because there are still no other bars in Boston. Okay, here comes the scene where Cindy very inappropriately informs Mark that she's a transsexual. He asks her what's wrong and to give him a clue. "Hold me close," says Cindy. "Closer." Mark grabs her butt and then feels her penis against his, apparently. "Surprise," says Cindy. Mark freaks and stumbles out of the bar. Cindy stands on the dance floor and looks really sad. "Maybe I should have just told him in private, like any normal transsexual would have done," we see her thinking.
The next day, Mark discusses his trauma with Richard, who just wants to say one thing. Richard's looking all serious, like he did in the episode where Billy died. He starts, "It's not easy, finding a person to love in this world. Whoever you end up with -- she won't be perfect." The piano starts playing. Richard continues, "Cindy is beautiful. When people see you with her, they're more impressed with you. What I'm trying to say is: don't dump her. Use her as bait..." The piano warps here. "...to attract other beautiful women. Ones without meat whistles." Mark runs out of the office. "Nobody loves a sage," says Richard. It was terrible, but it made me laugh.
Wanda tells Nelle and Ling that she doesn't see why they need to talk to her ex-husband. Nelle says, of Shirley, "As horrible as this woman is, she's pretty on-target." I say this every episode, but I hope Wanda's not paying them very much.
Elaine gives Ally some flowers that Jonathan brought over. He's in the Unisex. Elaine says, "There are probably three decent guys in this town. You've got two of them and Mark's got the other." Mark overhears this as he passes and is annoyed. "He took it hard," says Elaine, smiling. Well, I guess it's nice that everyone at the office knows now and can joke so casually about Mark's private life. Michael shows up to ask Ally to dinner. She acts really stupid because now both her boyfriends are in the office. She whispers to Elaine to detain Jonathan in the Unisex. Michael wants Ally to meet his kids at dinner that night. Jaws-esque music plays as Elaine physically keeps Jonathan from leaving the restroom. Ally accepts Michael's offer and then pushes him into the elevator as Jonathan drags Elaine across the floor. The scene is not funny at all, in case you thought maybe it was for once. Jonathan tells Ally, "You are so beautiful." How strange. He's not even fat or toothless. They make a date for the next evening.