We open on Sydney telling Lauren how great Simon's new relationship with a woman named Lily [played by Pam Dawber] who just were a new book that is 800 pages. Sydney tells her, Andrew and Zach that it's going really well. Then, they arrive making out in the elevator. She introduces herself to Sydney then Lily remembers she has a meeting in 20 minutes. Lily and Simon make a another date and she leaves. Simon seems to be really in love. Sydney then goes into her office and trips over Gordon,[played by Brad Garrett] who is lying on the floor distraught over his lover, Timothy leaving him after 20 years together. Simon wants to help so he gives him the keys to his apartment and tells him that they will figure out how Gordon can win Timothy back.
In the elevator, Andrew finds a set of keys. He asks Zach if they are his. He says they aren't and tells Andrew to leave them on the floor of the elevator. Andrew won't do that and is determined to give them back to their owner.
At Simon's apartment, he makes some tea as he asks Gordon what happened. Gordon replies That Timothy broke up with him because he's not spontaneous enough. Simon replies that "spontaneity is my specialty" and promises to help Gordon show Timothy that he can be spontaneous.
Simon has Gordon help him, Andrew and Zach come up with a pitch for Smart Specs, glasses you can wear and surf the Internet with. Simon tells Gordon to put them on and say the first thing that pops into his head, but Gordon can't come up with anything. Simon tells Gordon and he wants to help him plus get him back with Timothy since he doesn't want him around for his big date with Lily. Gordon then suggests that "you can anything" with the glasses so Simon, Zach and Andrew come up with a tune based on that idea with Zach playing acoustic guitar. Gordon gets overwhelmed and leaves and the guys decide that the song sucked anyway.
Sydney is hobbling around on crutches because her doctor says she sprained her ankle when she tripped over Gordon. Then, Andrew appears and asks Sydney or Lauren if the keys are either of theirs. Lauren then backs away and tells him that they're Jean's keys, because of the denim Jean keychain. Andrew and Sydney don't know Jean so Zach and Lauren tell them that she's "called the human tic" because she latches onto anyone who she has the smallest interaction with. Andrew still wants to return them, but covertly so he goes to Jean's office, drops them on her desk and moves to leave, but she catches him. She then corners him and insists on taking him to lunch as a thank you.
At Simon's apartment, he tells Gordon that he's invited over his new neighbors over so Gordon can learn how to socialize better. Gordon is wary saying that he likes to research people before he meets them. But, Simon ambushes Gordon when the couple arrives just then. They all sit down and Gordon suddenly becomes very knowledgeable about whatever topic the couple brings up. Simon then realizes that Gordon is wearing Smart Specs. Gordon then sees in the Specs that Timothy posted a picture of their beagle and has taken Gordon's last name out of the dog's name. Gordon tells Simon that it means that Timothy has given up on their relationship, but Simon disagrees. Simon tells Gordon to "not throw in the towel. Take a risk, win him back," but Gordon fires back that Simon isn't exactly the person to go to for relationship advice with his six failed marriages. "Love doesn't last, it dies, there are no exceptions," Gordon says. Then, Gordon leaves.
The next day, Andrew introduces Jean to Zach and Lauren. They've already had multiple lunches together and she's made him a few sweaters. When Jean walks away for a minute, Andrew tells Zach and Lauren that he's learned a lesson, "Don't be nice" since he gave Jean back the keys three days ago and she still won't leave him alone. Zach then says that Andrew must stay "Andrew the Good; so he and Lauren think they just need to find someone else to sic Jean onto. Sydney walks by on her crutches still complaining about her ankle. They all look at each other.
Simon and Lily are out on their romantic date at a restaurant. Simon has had all the courses planned out for maximum romance. Yet, Lily notices that Simon is acting different and asks if anything is wrong. He replies that "romance dies and love is a crock." Lily is disappointed to hear him say that since she tells him that she thought their relationship had a future. He fires back that they would probably go out a few more times, "one day wake up married then one day I'd forget to take out the garbage and you're after me with a couple of kitchen knives so let's just say 'check, please' and save ourselves years of torment.'" Then, David Copperfield appears as their waiter, but Lily tells him that he's too late, gets up and leaves.
Sydney picks up the ringing Smart Specs at the agency. It's Simon. Gordon hears Simon tell Sydney that he broke up with Lily because there was no point in trying if Gordon and Timothy couldn't make it and hangs up. Gordon feels terrible and Sydney pats him on the face then tells him to get out of her face.
Andrew throws Jean's keys in Sydney's path as she hobbles by. She sees Jean coming and tries to kick them away and flee before Jean sees her, but she's too late. Jean then latches on to Sydney, who tries to blow her off but then they commiserate over her sprained ankle, start talking about sprained rotator cuffs and walk off talking like friends.
Simon is singing at a karaoke bar with Timothy. Then, Gordon appears and starts singing Miley Cyrus' song "Wrecking Ball" to show that he can be spontaneous and gives a loving speech to Timothy before starting to sing badly. Timothy is delighted as he and Simon join Gordon on stage and all sing badly.
Simon then goes to see Lily with flowers to ask him to give him another shot and apologizes for his behavior. She calls him an "alien" then closes the door on him. Simon then morphs into David Copperfield and Simon comes out of another door. They then walk down the hall together as Simon asks Copperfield for three wishes and he replies, "I'm not a genie."