Two Timer Date - Television Tropes & Idioms

Character schedules dates with two different people at the same time. The character tries to keep both, going back and forth between the two dates without letting either know what's going on. Hilarity allegedly ensues.

Can also apply to other scheduling conflicts, where the character tries to juggle an event that he's responsible for attending, versus a more personal event that he really wants to attend.

If one of these scenes has a dress code of some form, expect a character to be caught wearing the dress for one event at the other.

Examples of multiple romantic dates:

Anime & Manga

Directly referenced in a Sailor Moon episode where Minako tries the same. Oddly enough, the two guys are both associated villains who brag to each other about their latest catch as if they were different people.
An episode of Samurai Pizza Cats, "Speedy's Double Time Trick", had Speedy try to go on a date with Lucille and Polly on the same day.
Found in DnAngel, where the protagonist and his split personality alter-ego have conflicting dates with twin girls, forcing him/them (and his family) to plan out a minor Xanatos Gambit to try to cover for it... using some interesting methods.
In the Ranma 1/2 manga, Ryoga invites Akane over to his house, but Akari (his would-be girlfriend) shows up ahead of time. When Akane comes by, he nearly goes mad keeping them separate and unaware of the other, while going back and forth to entertain them. Ranma (Akane's fiancé) is none too pleased.
- Ranma specifically expresses this displeasure by dressing up (again) and pretending to be Ryouga's maid, and "helping" Ryouga with his situation.
In Chapter 70 of Ai Kora, Hachibe ends up on a triple timer date: a trip to the amusement park with Sakurako, an eating contest with Yukari, and a ballroom dancing event with Ayame.

Comics

Find a Digest of Archie Comics. I guarantee you there will be at least one example of this type of plot therein.

Film

In 27 Dresses, Jane is a bridesmaid at two different weddings on the same night.
In Mrs Doubtfire, Robin Williams' character has conned his own (estranged) family into accepting him, in the persona of a kindly middle-aged woman. Naturally, he ends up booked for dinner with his family as "Mrs. Doubtfire" at the same time as he's supposed to have a business meal with a TV executive. Hilarity, and many quick costume changes, ensue.

Literature

I Married An Earthling offers this plot as an example of a particularly bad episode of a putrid sitcom that main character Chester's younger brother is on.
"Horrors, Devon has two dates! He seeks advice from his pals Benny, the dumb jock, and Oscar, the smart nerd. Hilarious hijinks too nauseating to mention ensue."
The Rise of Renegade X has a great example where our intrepid protagonist is simultaneously on a Supervillain date to steal an heirloom ring back from an antique shop and a Superhero date to keep his stepmom's antique shop from being robbed of a priceless trophy that cost her her power. Yes, it's the same job from both angles. Even he's not sure who he wants to win.
In Curse Of The Wolfgirl Markus remembers a little too late that he is taking one of his girlfriends to an opera-party at which the other girlfriend is a senior member of the stage-design team. It was probably a relief when the werewolf hunters attacked.

Live Action TV

In the Cheers episode "Cliffie's Big Score", Cliff has a date with both Carla and Diane.
Three's Company did this more than once, twice with Jack running back and forth between different dates in different apartments.
In the Malcolm In The Middle episode "Malcolm Dates a Family," Malcolm engages in a bit of Lamp Shade Hanging when he realizes he's scheduled simultaneous dates: "This is like that episode of... well, everything."
Every Superman TV series has done this with the title character's two secret identities. In a few cases, both dates have been Lois, meaning she was doing this, too.
Popular with guest actors in shows where the leads are twins. Sister Sister did this a few times. In these series, the date usually leads to a Twin Switch.
Subverted/Parodied in an episode of 3rd Rock From The Sun: Harry's stupidity leads him to believe that he has a date with twins and fulfills the usual elements of this trope, never realizing that said twins are the same person. There wasn't any deception on the girl's part. Harry's just plain stupid.
Naturally Sadie episode "The Last Waltz".
One of the funnier Family Ties eps is based around Alex, this trope, and a school dance. The deception hinges on him keeping the colour of the carnation in his buttonhole straight.
In the "Casino Night" episode of The Office, Michael, who often doesn't even have one date, accidentally gets one with his boss and real estate agent.
Smart Guy had TJ's dad hook him up with a date, TJ's brother hook him up with a date, and TJ's sister hook him up with a date. The fact that his not-so-smart big brother's best buddy is in charge of making the plan to keep his 3 dates separate but entertained only makes matters worse.
Sex And The City had Charlotte do this, and get busted after she faked sick to get out date #1 early.
Bones had Brennan try this as well, though she didn't mean to. She just accidentally scheduled them both to pick her up at the same time.
Saved by the Bell had at least one episode that used this. I swear it involved Screech dressing like a girl, too.
Gary from Goodnight Sweetheart did this once, with the variation that the two dates were actually decades apart, but since he could only travel forward/backwards by a fixed amount of time, for him they were effectively at the same time.
A Brady Bunch episode has Peter trying to pull one of these off after the Identical Stranger he's just met at school has to break off a date on the same night Peter has a date of his own.
A Show Within A Show on iCarly used this trope to show how stylistically sucky the shows on TV are.
- Played straighter in "iWon't Cancel The Show", where Spencer has scheduled his date with "sophisticated" Candice and has to do iCarly at the same time because Sam is in jail.
This happens on Sanford And Son in an episode where Fred becomes a gigolo (I'm not making this up). He makes dates with three women and has them meet him in the same restaurant and goes from table to table without them noticing.
Not restricted to comedy, it was played straight in Quantum Leap episode, A Tale of Two Sweeties where Sam, in the body of a bigamist, scheduled his two dates at the same time in the same cinema and had to keep going back and forth between them.
The Blackadder II episode "Beer" has a variant of this, with Blackadder attempting to host two different parties in his house simultaneously, one a dinner with his fanatical Puritan relatives and the other drinking contest with Lord Melchett.

Video Games

In Custom Robo for the Game Cube, you (a bounty hunter) are called to break up a fight between two would-be dates. When you get there, the girl they were dating explains that she had accidentally scheduled both dates at the same time, and she didn't cancel either date. Instead, she just let the two meet each other. She then leaves you to take care of her boyfriends. Ironically, the two later become best friends.
One sidequest in the Nintendo DS remake of Final Fantasy IV has the party briefly helping ~~Namingway~~ Cheatingway employ this trope by distracting one of his dates with small talk while he dates the other.
One chain of missions in Final Fantasy Tactics A 2 has you provide clan members to date up to four people for a chronically overscheduled petitioner. Amazingly, the lucky ladies care more about the level and MVP trophies of their dates than they do about things like species and gender.

Webcomics

In Blip, we find out that being a cyborg with access to robotic duplicates makes short work of scheduling multiple dates at the same time.
Mary: After we're done, their memories will be downloaded into mine. I hope that I had a good time.

Western Animation

Chuckie in All Grown Up! attempts this with a Secret Identity.
Hey Arnold!, "Arnold's Valentine", has this forced upon Arnold, when his French penpal Cecile (actually Helga pretending to be Cecile) supposedly arrives for a surprise visit "coincidentally" at the same time as Arnold's previously planned date with Ruth McDougal. His solution is to take them to French restaurants across the street from each other and bounce between the two. Arnold manages to pull it off well enough to fool Ruth, and when "Cecile" confronts him for his dishonesty, the real Cecile shows up for a real unannounced visit, making Helga-as-Cecile's accusations highly hypocritical at best and saving Arnold on that front as well.
Futurama lampshaded this trope and mentioned the Three's Company episode referenced above. Fry is forced to pretend to date Leela and Amy at the same time. While dealing with Leela's stalker/one-sided-love-interest (the ship's captain) and Amy's parents. While at the same table as all of them.
The second season of WITCH saw Cornelia using her half-transformed Guardian state to date one of her friends' older brother by appearing to be a few years older than she was. Ethics and Secret Identity issues aside, Cornelia already has a shaky relationship with her earlier paramour Caleb. It culminated at a date in a skating rink where Cornelia/"Lily" shows off her skating prowess and uses a snazzy light show courtesy of Will to juggle both boys until she and the brother kiss where Caleb can see them. Before she can resolve things with Caleb, the forces of evil come calling...

Examples of other scheduling conflicts:

Anime and Manga

Detroit Metal City does this trope at least once, with Negishi having to switch between eating cake with Aizawa and being Krauser for a new album release.

Film

This is the device employed for the climactic sequence of the Dan Ackroyd movie Doctor Detroit — his character is running back and forth between a society function and a pimps'/hookers' bash, both in the same hotel, and has to switch clothes and personae between them as well. With predictable results.
A scene in the film Mrs. Doubtfire combines this version and the two-identities version, with a children's entertainer, played by Robin Williams, switches between a dinner with his boss and a dinner at the same restaurant where he must pretend to be the elderly babysitter Mrs. Doubtfire. He gets caught by his boss when he forgets to change back, but manages to convince him that this is his idea for a new character.
- It was wackier than that. He had also stuffed pepper into his ex-wife's new boyfriend's dish, knowing that said new boyfriend was allergic to it - this scheme ends up working too well, causing a dangerous choking allergic reaction. Williams rushes across the diner to perform the Heimelich Maneuver, and ends up exposing himself to his family in the process.
In Hannah Montana: The Movie, Miley/Hannah finds herself juggling between a dinner date with a boy (as Miley) and a reception with the mayor (as Hannah). At one point she finds herself wearing a lobster bib at the wrong dinner.
This happens in The Secret of my Success, when a mailroom clerk played by Michael J. Fox decides to give himself a promotion. He secretly holds down two jobs and uses the elevator for a changing room when he dashes back and forth to fulfill his responsibilities. He even manages to carry off the charade on a weekend trip and manages to have a girlfriend while having an affair with his own aunt.
Superman IV: The Quest for Peace pulled this when Clark had to go on a date with Lacey and give an interview to Lois as Superman at the same time. Thus Hilarity Ensues as even Superman has trouble maintaining the charade despite having superspeed and all that. Made all the more annoying because Clark had outed himself to Lois as Superman twice in the film series, one of those times in this movie, but erased her memory for reasons inscrutable (aside from Shipping Bed Death), thus making the entire sequence avoidable.

Literature

The protagonist of William Sleator's The Duplicate accidentally schedules a date as the same time as his grandmother's birthday. In order to avoid the Hilarity that would ensue if he tried to run back in forth between the two, he uses a mysterious device to duplicate himself, so that he can attend both. Then his duplicate wins the coin toss and the original has to go to the grandma party, and it all goes downhill from there.

Live Action TV

Seen in the Blackadder episode "Beer," where Edmund winds up scheduling a dinner with his Ultra-Puritan relatives and a drinking party with Lord Melchett's buddies at the same time, down the hall from each other. At one point he returns to the Puritan dinner table without removing the fake comedy breasts he was wearing at the drinking competition ("you appear to be wearing devil's dumplings!") and has to pass them off as earmuffs. He also has to explain why one of the guests from the drinking contest burst into the room yelling "Great booze up!!!" Then the Queen shows up and things get really crazy.
It also happens, with a healthy dose of Lampshade Hanging, in Boy Meets World, when, in preparation for such a ruse (involving Topanga's birthday party and a wrestling match), Corey watches the aforementioned Flintstones episode. For the remainder of the episode, he makes comments about the prospect of being hit on the head with a frying pan. At the climax, he and Shawn refer to each other as Fred and Barney.
Power Rangers Ninja Storm has an episode where Tori uses her powers to both attend Shane's skateboarding competition with Dustin and see a movie with Blake and Hunter.
Friends does this in its "The One With The Two Parties" episode, where Rachel's recently-separated parents both show up for her surprise party, necessitating the creation of two simultaneously-held (and attended) parties happening across the hall from one another.

Real Life

The Roman general Gaius Marius did this is in his last few weeks with two diplomatic delegations, feigning bouts of dysentery in order to rush from one end of his house to the other. It worked, but didn't help him much; he died quite soon afterwards and was in no real position to oppose a returning Sulla anyway.
In one of his Dilbert books Scott Adams gives the example of a man who had received simultaneous job offers from two firms in the same office building. He accepted both, and negotiated that he would start at 8 am in one firm and 9 am in the other. He'd go into the first firm at 8, log onto his computer and so on, then at 9 he'd claim to have a meeting, go to the other firm, log on there, work for an hour or so, then go back to the first firm... and so. In this manner, he managed to draw two paycheck for several months, until one day there was a fire alarm and he had to figure out which group of workers to stand with...

Web Comics

In The Wotch, Anne plans to play video games with Robin, go to band practice, make up a test she missed, and help plan the school dance all at the same time. Being a magic user, she summons up three duplicates. Unfortunately these duplicates represent aspects of her personality, and shortly afterward, other aspects of her personality leave her as well. To make matters worse, they cause all sorts of trouble, some of which Anne doesn't even learn about until much, much later. Nice Job Breaking It Hero, and I'm sure that rescheduling some of those events would have been ''far'' more painful.

Western Animation

In one episode of The Flintstones, Fred has a big meeting of the Water Buffalo Lodge, but he has also promised to be at Pebbles' birthday party the same night, so he rushes back and forth between the two. He is eventually caught when he forgets to remove his Water Buffalo hat before entering the party.
- In another episode, Fred had a Water Buffalo Lodge bowling tournament on the same night he promised Wilma he'd take her out to dinner and a movie.
Kim Possible had to chose between checking up Monkey King with Ron or spending time with her annoying cousin Larry. The choice was with Ron, until it's revealed that she did chose Larry and that Kim was a projection made by Wade. Cue All Up To You.

Sometimes, the character ends up spurning the big personal event altogether, to deal with the other commitment:

Anime

Mew Ichigo of Tokyo Mew Mew misses her date because a monster ate her cell phone and is threatening to poison the whole city. (And in the manga, it wasn't even her that got to save the day in the end anyway.)

Comic Books

A standard plot for Archie Comics.
Superman will occasionally have to appear as both Clark Kent and Superman. He'll get Batman or someone to help. In fact, I'd bet most long-running superhero comics with secret identities have run into this.
Spider-Man and Daredevil seem to have a standing agreement to help each other out this way. It helps that the two have similar builds and each's abilities let him perform a decent enough approximation of the other's (at least enough to fool the average Marvel Universe civilian).

Western Animation

Rocket Power, "The Big Day": Otto, Twister and Sam withdraw from a skating contest to save a wedding.
All Grown Up!, "Runaround Susie": Susie doesn't participate in a singing audition because she's at a linguistics contest instead.
The Simpsons, "The Bart Wants What It Wants": Bart avoids a school dance that Greta invited him to in favor of watching Principal Skinner perform at a comedy club.