It's Valentine's Day at 30 Rock, and Lemon resolves to remove herself from the entire equation. She schedules oral surgery so that she won't have to take part in the contrived love fest. And, frankly, her plans don't seem entirely off-base when given the alternatives: Frank is trying to scam a wingman for his date with the rat-faced lady who cleans the urinals. Toofer might just throw himself on that grenade if it means missing a blind date with an "urban." Pete will do the usual -- get wasted in his garage while his wife and kids visit Niagara Falls. Tracy, his wife Angie, and a hot tub full of chili will somehow be entangled. And Jenna thinks she's got a standing date with her stalker (Horatio Sanz). That is, until she doesn't hear from him in advance of the big day. She tracks him down to the chicken shack where he works to find him a changed man, on his meds, no longer instructed by some greater force (his dog Brandon and the electricity shooting from Jenna's head) to watch Jenna sleep and replace the food in her refrigerator with baby doll heads. Jenna takes the rejection badly.
The only person who seems to have plans with possibility is Jack. Still wobbly from his roller coaster romance with Nancy, he's set up three loose (in more ways than one) dates for Valentine's night. Jonathan will call him at various points in the night with a fake appointment, and Jack will give the proverbial thumbs-up or –down on that moment's date. Except a kink arises when he appears on a CNBC show and strikes up a rapport with the anchor (Elizabeth Banks). Jonathan makes the yea-or-nay call while they grab a drink. Jack says "Yea," but the brassy blonde spots his strategy and leaves the date anyway. Not before sending a gift the next day ensuring that the game is on. Jack impresses her with another ruse, and they have a one-night stand.
The next morning, Blondie begins to blow him off for being a playboy with no hope of commitment. Then someone from Lemon's dentist's office calls. It seems LiLem (™ Tracy Morgan 2010), needed an escort home after her heavily anesthetized anti-Valentine's Day surgery. After she was rebuffed by literally every person at 30 Rock, she decided to go it alone, claiming her boyfriend Astronaut Mike Dexter would pick her up, then make a break for it when the opportunity arose. Just one problem: People on surgery-grade pain killers aren't that good at running away. They are, however, good at hallucinating that their ex-boyfriends have come to save them from a life of lonely trips to the dentist. And seeing Jon Bon Jovi in ficus plants. So good at these things, indeed, that they have to be bailed out by their playboy bosses and his high-powered news anchor date on her walk of shame. And that's pretty much Valentine's Day in a nutshell at 30 Rock.
30 Rock. Lemon encounters Pete, whose daughter is selling Valentine's cookies. Lemon launches into a tirade about the commercialization of Valentine's Day, yadda yadda yadda, and ends with an entirely inappropriate-for-a-child recap of all her recent Valentine's Day misadventures. No matter, she buys the cookie anyway in honor of the birthday of Anna Howard Shaw, famed American suffragette. Little Evelyn Hornberger is not impressed as Pete drags her away from the crazy lady he told her about. The very same crazy lady who is screaming to anyone who will listen (which would be pretty much nobody), "A happy Anna Howard Shaw Day to all!" Credits.
Upstairs, Lemon helps Jack pick a tie for a CNBC interview that night. She wonders why he's not spending his Valentine's Day with Nancy, but Jack says his romance with her has been too much of a roller coaster. Right now he just wants a fling. As such he has three dates set up around town. At an agreed-upon time, Jonathan will call to interrupt his date. If he's bored, he's got an out. If he's intrigued, he'll loudly announce that he's got important plans and can't be bothered, which will impress the woman enough for her to expose her front-clasp bra to him. At least that's the rough outline of his plan. He asks about Lemon's plans. She has scheduled a painful dental procedure, which will guarantee she'll be doped up enough to enjoy the latest Lifetime movie before passing out with drool dripping down her face. Jack snarks at her vigorous spinster-ness, but she unabashedly owns it.
Downstairs, Kenneth is clipping Tracy's nails when Jenna comes in to ask if she's received any packages. Apparently the holiday of love is a big time of year for her stalker. Except she hasn't received anything. Kenneth foolishly assumes that less stalking would be a good thing, but Jenna sets him straight. Without a loony on her tale, she's practically nothing. Then paranoia sets in as she wonders if her stalker might have moved on.
Writer's room. Lutz asks the others for sex tips in an effort to continue his annual farce that he has a girlfriend named Karen who's coming into town. She's real, he insists! As proof, he offers up her personal website address: www.jdlutz.com/karen/proof. Toofer, in turn, is kvetching with the "urban" (read: black) blind date his cousin's set him up with. Frank tells him to bail on the blind date and come on a double date with the "ugly" sister of his date -- "that load with the messed up teeth who cleans the urinals." Toofer briefly considers acting as the Pauly D of TGS right now, throwing himself on a grenade for his boy. Of course, that makes Frank The Situation. Hmmm... Lemon tells about her hot "oral" action. Before they can get too excited, she clarifies she's getting oral surgery and skipping the holiday on doctor's orders. Cerie interrupts to say the doctor called to ask who's taking her home. Pete tells her it's an insurance thing, which Frank backs up with his own horrifying drugged-out dental anecdote. Lemon asks Pete to pick her up, but he'll be otherwise engaged getting wasted in his garage while his wife takes the kids out of town.
Meanwhile, Jack makes his appearance on CNBC's Hot Box with Avery Jessup (Elizabeth Banks). They trade zings for the token liberal wonk who rounds out the panel. After a few rounds of the beat-the-clock portion of the segment, Jack and Avery realize they're peas in a Conservative pod. They go a few more rounds before she asks Jack out for a drink. Needless to say, the wonk won't be joining them.
Back at 30 Rock, Lemon asks literally everyone she runs into to pick her up at the doctor. One by one she is rebuffed. Tracy has his own sick plans, and I don't mean sick in the hospital sense. Likewise, Jenna has plans to stalk her stalker. Kenneth is attending an abstinence rally with "gender neutral" masks that are more psychotic serial killer than chaste devotee. Worst of all, the nameless janitor takes sadistic pleasure in smilingly saying hi to Lemon just so he can turn her down, too.
Elsewhere, Jenna tracks down her stalker (played by the positively svelte Horatio Sanz). They have a twisted break-up talk in front of the entire Fried Chicken Palace (Maynard's place of employment).
Meanwhile, Jack and Avery impress each other with their fancy schmancy resumes. She went to Choate, then Yale, then the Peace Corp, a company that drilled for oil in gorilla habitats. (Not the Peace Corps, God no!) Jack finds common ground from his experiences talking to gorillas as an animal tester at GE Medical. He asks if she's seeing anyone. She says no but Jack fits her mold of "commanding salt-and-pepper types," stemming from a sexy memory from Reagan's attempted assassination. Jack's phone buzzes. It's Jonathan, who is positively giddy to have a secret with Jack. Giddy enough, in fact, that he overshares an anecdote about the time he hit-and-run an old lady in Arizona. Good times. Jack goes with his Plan B, to impress his date by cancelling his fake conference call with Geneva. He hangs up, and Avery immediately calls his bluff since she's smart enough to know it's well before business hours in Switzerland. Jack apologizes, but it's too late.
The next day, Lemon desperately asks Frank one last time to give her a ride home. No can do. His hideous cleaning lady friend came through. He lords it over Lemon that she's stuck in the same "crappy Valentine's Day boat" as everyone else. She insists she doesn't need a date, just a ride. Frank tells her to own up to the fact that she wants a little affection just like everyone else. She winces at the pain from her tooth. Frank adds that she's even worse off because she has an infection (not affection, bah-dum-bum) that could spread to her brain and kill her. Lemon shoots back that her ghost will haunt him from the grave. He counters that her ghost best be prepared to see some disgusting stuff. Touché, Frank. touché.
Upstairs, Jack revels in showing Lemon the clock Avery sent him. It's set to Geneva time, which means she found him intriguing enough to move forward. It's game on. An impressed Lemon notes Avery made it onto Maxim's "I'd Rape That 100." Jack says she's smart, too, which will make his eventual triumph in seducing her all the more satisfying. Lemon, on the other hand, can't get no satisfaction. Even the male escort she resorted to hiring for a ride home from the hospital can't make it now that he's had a Chlamydia flare-up. Wow, nothing says Valentine's Day like all those things slapped together in one sentence! At any rate, Jack has no time to worry about such trivialities. Nor will Lemon, as he's commissioning her to put together a VIP room for that evening's show. He's invited Avery. Lemon doesn't know how she'll bring together a bunch of real VIPs for the fake VIP room on such short notice. Jack suggests she invite NBC Artist in Residence Jon Bon Jovi. The duties of this "not-stupid" program Jack conceived apparently entail competing on Top Chef and strumming the Nightly News theme when necessary. Jack tells her to get going. He's got to pull out the "Jack Donaghy A Game." Lemon mocks this notion, so he puts on the full charm offensive, and she practically starts giggling like a school girl.
Downstairs, Kenneth finds morose Jenna reminiscing over the good times with her stalker. She even shows him one of Maynard's letters to her ("Jenna, I was in your bedroom last night. I left a gift in your toilet. You will be my bride some day."). Kenneth remains perplexed that Jenna would miss her stalker, so Jenna sadly explains that Maynard was her longest relationship, except of course for Doug. Before Kenneth can tell her not to explain, she spits out that Doug is her vibrator. Of course.
Down the hall, Lemon calls to inform the doctor's office that she does not have someone to pick her up and is not ashamed of that fact. She defensively says she can do everything a person in a relationship can do, and can even do some things better -- like monologues. The receptionist says Lemon can leave alone if she signs a liability waiver.