Michael, David and Micky show up at the KXIW-TV station to enter a Rockathon contest in which the prize is $500. Michael coaches the others to act like they don't need the money when they really do. But Jerry Blavat, a DJ who is also the MC, insists it's only for groups of mixed sex, and they must have a girl in their group to enter. So they decide one of them has be dressed up as a chick!
Later, with Peter, The Monkees have to decide on a volunteer basis which one of them makes the best looking girl, and automatically, it's David Jones! David is reluctant, convinced that he couldn't pull it off just as he falls into the janitor's closet and reemerges with a mop on his head which convinces a flirty janitor. Back at the pad, the guys help David dress up in drag and to help him act like a woman, with Peter's book on how to act like a feminine female. Soon they change David's appearance and teach him a mincing walk, using a rope, frying pans, and a heavy tome which they give him to balance on his head. Later they plan to enter the contest but David insists that it will never work and they'll find out he isn't girl. Elsewhere, Daphne, a member of a female quartet The West Minstrel Abbies disguised as a guy, "William The Conqueror," tells her band mates that they'll bound to find out she's not a boy. That night at The Rockathon, the boys watch The West Minstrel Abbies, 3 girls and a boy respectively comprised of Harmony, Melody, Caphophone, and William The Conqueror (Daphne duded up as a dude), do a speedy rendition of "Last Train To Clarksville" at 78 RPM, and score a 98.6 on The Applause-O-Meter, its highest reading! The Monkees go on next with their act, singing "The Door Into Summer" and doing everything possible to keep David from fleeing the stage, while Jerry starts becoming smitten with "Miss Jones". The Monkees tie with The Abbies on The Applause-O-Meter with a 98.6 reading, so Jerry announces they both groups will return to for a rematch.
At the pad, The Monkees won't let David take off his drag getup just in the offchance case someone from the station shows up; suddenly, as if on cue, there's a knock on the door from Jerry with a boquet of roses for Miss Jones! While Micky, Michael and Peter hide behind the couch, Jerry makes numerous passes at "Miss Jones," asking him out and offering to help him win if plays his cards right but David nicely refuses and sends him on his way just before he kisses David's hand. Micky, Michael, and Peter go out to dinner, but David stays behind; so does Daphne when her friends go out, since both of them would have to dress in drag. Both groups' mates offer to bring them back a tuna sandwich. David and Daphne, however, don't want to spend a Saturday night home alone and each decides to go out alone, to the Southside Branch of The Some Little Out Of The Way Place Where Nobody Goes Café, outside of their drag outfits. When they ended up seated at the same table, they become starry-eyed as it's love at first sight but David sees Micky, Michael and Peter come in and he rushes away, leaving behind a high heel shoe for Daphne to pick up. Back at the pad, David rushes into the bed under the covers and pretends to be sleep just as the others arrive back. He fakes waking up and nearly gives himself away by inadvertently naming the place where they ate. Then he discovers that one of his high heels is missing!
The next day, at the KXIW-TV studio, The Monkees return for the rematch with The West Minstrel Abbies---and David again masquerades as "Miss Jones," much to his chagrin. David nearly slips up again about Daphne when questioned him about his missing high heel but he quickly covers his tracks. David heads outside when all of a sudden Jerry Blavat arrives, checking his watch, so, in order to dodge any impending advances, he ducks into another dressing room, where he reencounters Daphne. He quickly realizes that she doesn't recognize him dressed in drag and tries to leave but she grills him about his missing high heel which looks like the one she has. Then David takes off his wig and confesses and then Daphne also reveals herself as the male singer of The West Minstrel Abbies; both realize that their deceit is wrong. When David confesses to Jerry Blavat, he becomes outraged and tries to disqualify The Monkees for not being a mixed group, but David explains that they are a mixed group and to prove it, The Monkees perform "She Hangs Out" with The West Minstrel Abbies now in black miniskirt dresses, long hair and highheeled shoes as backup dancers, joining them as a mixed group, which impresses Jerry.
David chats with Charlie Smalls (The Wiz [Universal, 1978]) about soul in music, and then sing a tune which they both composed, "Girl Named Love."