Two-Timer Date

""This is like that episode of... well, everything.""

- Malcolm, Malcolm in the Middle

Character schedules dates with two different people at the same time. "You can't be two places at once," the character's friend says. Rather than doing the sensible thing and cancelling one of the dates, 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.

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 D.N.Angel, 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 Batman Gambit to try to cover for it... using some interesting methods.
 * In the Ranma ½ 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 fiance) 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.
 * And amazingly he pulls it off.
 * In Kimagure Orange Road, Kyosuke habitually goes on two timing dates with Hikaru and Madoka. It helps that he can use his psychic powers to create distractions and teleport around. For example, while riding a roller coaster with Hikaru he teleports to his part time job with Madoka, then teleports back and almost gets run over roller coaster. One Christmas he even rewinds time so he can go to the same party with both girls.
 * In Carnival Phantasm, Shirou and Shiki have to plan around three and five commitments, respectively. Shiki's plan starts with him being in two places in exactly the same time, and gets even crazier from there.

Comics

 * Find a Digest of Archie Comics. I guarantee you there will be at least one example of this type of plot therein. It's pretty much impossible for a story to do this plot now without some sort of Lampshade Hanging. One comic had Dilton calculate that Archie's done this 1,797 times before!
 * Even Jughead has done this. Jughead, who typically refuses to go on even one date. Hey, it was an excuse to have two meals.
 * In The Simpsons comic, "Springfield's Typical Teen-ager", a teenage Homer accidentally plans a date with Mr. Burn's niece and Marge at the same time forcing him to drive back and fourth. Barney even compares Homer with Archie Anderws.

Literature
""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.""
 * 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.


 * 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.
 * Threes 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 Lampshade 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 dual identities. In a few cases, both dates have been Lois, meaning she was doing this, too.
 * In episode of The Adventures of Superman, Superman solved this problem by literally being in two places at once—he split himself into two bodies.
 * 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.
 * Similarly, said big brother also later ends up asking twins out on a date completely by accident (he asked one girl out, and then asked her sister out thinking she was the same girl until TJ pointed it out to him), thus causing him to try and create a fake twin, only for it to unravel quickly.
 * 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.
 * He tried to prevent suspicion by leaving the restaurant through the bathroom window while on the way to the time portal. This led Yvonne to wonder why he was (apparently) spending so much time in the bathroom, leading her to ask him "Are you bulimic, or pregnant?"
 * 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.
 * in an Early episode of the original Battlestar Galactica, Starbuck has a date with both Cassiopia and Athena, at the same time, on the same luxury restaurant ship. He is aided by the steward of the restaurant, who calls his behavior 'Very pre-War!'
 * 7th Heaven had this in Busted. Well, kind of. It actually was scheduled for one date, but Marsha Chalker, Simon's date, started leaning more towards Matt than Simon, with her even going as far as to look at Matt while kissing Simon goodnight.
 * In ER, Mark Greene, fresh after his divorce, being rather clumsy at asking women out, happened to invite three of them to the same time.
 * Young Indiana Jones does a three-timer in "The Scandal of 1920".
 * One episode of Kenan and Kel had Kenan take three separate girls to three different movies in the same theater.

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 A2 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.
 * In Magical Diary: Horse Hall, after setting up a date with Ellen or Virginia, you can accept a date with Damien for the same weekend. You can either tell your original partner that it's canceled, or try to go to both at the same time. Unsusprisingly, this doesn't work out well.
 * Implied in one of Paz's diary tapes in Metal Gear Solid Peace Walker. Basically, Kazuhira Miller went on a date with two female members of the Militaires Sans Frontieres at the exact same time, and it is implied that Miller has done this before. When the girls report it to Big Boss, he proceeds to go and beat up Kaz in the showers.

Webcomics
"Mary: After we're done, their memories will be downloaded into mine. I hope that I had a good time."
 * 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.

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.
 * Futurama lampshaded this trope and mentioned the Threes 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 brothers 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
 * Happened once to Babar, where he invited Celeste to a ball only to find out he was also expected to entertain the daughter of a visiting king. When he couldn't bring himself to un-invite Celeste he decided to try this trope, with the usual degree of success. He eventually manages to pawn the visiting princess off on a friend, and once he's explained himself Celeste was actually touched that he'd risk a diplomatic incident to keep her happy.
 * Justice League: Subverted. The Flash successfully pulls off dating two women simultaneously. Being the fastest man alive has its perks.
 * In the Phineas and Ferb episode "A Real Boy", this trope is referred to in passing as a sit-com cliche by Dr. Doofenshmirtz (when he gets embroiled in a case of Poor Communication Kills with his daughter).
 * In The Man Called Flintstone Fred must go repeatedly between a family gathering with Betty and Barney Rubble and Wilma and a date with Tanya.
 * The Jetsons has George's boss force him to go on a date with a star to get a contract signed. Of course, this happens just as George is on a romantic outing with his wife.

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.

Comics

 * Done in the pages of Suicide Squad where Captain Boomerang starts using the identity of Mirror Master, forcing him to rapidly change in and out of costumes to hide his second identity from his teammates.
 * SpongeBob SquarePants "Overbooked" is a SpongeBob SquarePants episode from season six. In this episode, SpongeBob must be at Patrick's birthday party, help Sandy with her presentation, and help Mr. Krabs build a telescope, all at the same time.

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.
 * 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.
 * In 27 Dresses, Jane is a bridesmaid at two different weddings on the same night.
 * In the upcoming movie The Sitter, Noah has to balance between babysitting an old neighbor's kids (although he was primarily focused on another kind of "kids" when arriving to do the babysitting), as well as going over to a female friend's place to have sex.
 * In A Goofy Movie: Max has this trope forced upon him. Basically, he was sent to the Principal's office when an attempt to impress Roxanne backfired, and he was excited that he'll get a date with her that weekend. Unfortunately, thanks to his celebrating that he got a date, the principal assumed the worst and called Goofy, making Max's behavior seem worse than it actually was, and thus Goofy decided to take his son on a fishing trip... the same weekend as his date with Roxanne.

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.
 * In the second book of Dork Diaries, Nikki, the protagonist, is meant to be doing three different things at the same time: hang out with her best friends at the Halloween dance (dressed as a trash bag), be on a date with her crush at the Halloween dance (dressed as Juliet) and be helping out at her little sister's ballet class Halloween party (dressed as a giant rat).

Live Action TV
"Corey: What happens if something goes wrong? Shawn: I have another plan, but it involves Jonny Quest."
 * 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.
 * In Edmund's defense, he didn't schedule the drinking party, the Queen did. And you don't say no to Queenie.
 * 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.
 * Shawn preps him up on the pitfalls he faces, including the eventual inability of Fred to keep track of the lies and mixing up costume elements, which Corey inevitably ends up doing anyway by showing up at Topenga's ball with in a tuxedo and Vader wrestling mask.


 * 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.
 * In one episode of Frasier, he juggled romantic and nonromantic commitments. He was trying to make a date with a woman but kept standing her up due to accidents or Contrived Coincidences. He scheduled the third attempt for his birthday. His friends threw him a surprise party. He finally snuck out of his own party too late for the date but managed to catch the woman in time to show her his date of birth on his driver's license and prove he was really willing to spend his birthday with her. (This immediately turned out to be a horrible idea, of course.)
 * In Home Improvement, Tim Taylor attempts to go to a Japanese Suite with Jill Taylor for their anniversary. Unfortunately, one of the executives for the show ended up scheduling a meeting with one of the higher ups not only at the same location, but on the same day, forcing Tim to balance out the two occasions, predictably failing.
 * On That's My Bush!'s first episode, Laura demands a date night with George at the same time he has to have a meeting with the leaders of the pro-life and pro-choice campaigns. The maid even Lampshades that this won't work, as apparently other presidents have tried it.
 * In an episode of Sabrina the Teenage Witch, a family get-together on Halloween conflicts with a party Sabrina wants to make an appearance at. Being a witch, she creates a duplicate that can only say three phrases and sends her to the mortal party (Salem points out her aunts would be more likely to catch on than her Muggle schoolmates.) Sure enough, her aunt Hilda tries to send a duplicate to the witch party which Zelda unmasks almost instantly ("Hilda, what color is my dress?" "Pass the potatoes!")

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 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 helping Ron deal with Monkey Fist or spending time with her annoying cousin Larry. It appeared that she'd gone on the mission, until it's revealed that she did choose Larry and that the "Kim" accompanying Ron was a projection made by Wade—a deception unknown to Kim until Wade 'fessed up to it while telling her about what Monkey Fist has become. Cue an All Up to You moment for Ron....
 * In one episode of Arthur, Francine has to go back and forth between a bowling tournament that she has to win with her friends and a relative's bar mitzvah (because the Frenskies suddenly became Jewish in the Christmas Episode). She doesn't end up winning the bowling tournament and also misses the best parts of the bar mitzvah, so she learns her lesson in the end.
 * In one episode of SpongeBob SquarePants, the titular sponge has to help Sandy demonstrate an invention of hers, attend Patrick's birthday party, and build a telescope for Mr. Krabs.
 * In the My Little Pony Friendship Is Magic episode "Sweet and Elite", Rarity has to constantly switch between going to her friend's birthday party and a rich stallion's garden party. Notably, this sequence is mercifully condensed into a montage that lasts less than a minute.
 * In the Phineas and Ferb episode "Run, Candace Run", Candace ends up having to volunteer to read to kids at the library with her mother on the same day she accepted an invitation to Jeremy's family reunion, and uses a pair of Super Speed boots developed by her brothers to try and be in two places at once.

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...

Blowing it off completely
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 one's abilities let him perform a decent enough approximation of the other's (at least enough to fool the average Marvel Universe civilian).

Film

 * Max Keeble's Big Move had Max missing out on a going away party held by Megan and Robe, his friends in favor of going to a milkshake party with Jenna, which also qualifies as a What the Hell, Hero? moment.
 * In Mr. Popper's Penguins, it looks like Tom is going to do this with his scheduled meeting with Van Gundy and his date with his ex-wife Amanda, both of which were to take place at the Tavern on the Green. He ends up completely ditching the meeting; as he leaves the restaurant with Amanda, Van Gundy is seen peering out the window at them. This causes her to reconsider her earlier assessment of him as a shameless businessman who cares only for money.

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.
 * An episode of The Fairly OddParents has Timmy using magic to travel back and forth between Chester and A.J. The three had planned to watch a TV Movie together (Crash Nebula meets the Crimson Chin), but the latter two had gotten into a fight over which of the characters were better. They both invite Timmy to their houses to watch it with them alone, and Timmy does his best to juggle the two, in the end developing a plan to get the two to stop fighting.
 * Ned's Newt once exaggerated this by having Newton set up Ned for a date with every girl in school (at the same time, of course).
 * In an episode of The Mask, Stanley is handcuffed to Lt. Kellaway, who's trying to prove he's the Mask. Meanwhile, the villains Putty Thing and Fishguy are attacking. So, Stanley has to find ways to put the mask and becoming the hero without the cop noticing.