Never break up with a girl on her birthday.
Ted reconnects with an old flame and soon remembers why he dumped her in the first place. Barney pays Robin to say outrageous things on the air.
This episode provides examples of:
- Action Girl: Natalie, who takes Krav-Maga classes.
- An Aesop: Robin learns the importance of her job as a reporter after interviewing an old Hansom cab driver.
- Arc Symbol: The titular shirt which Ted wears throughout the episode. Ted finds an old shirt in his wardrobe; a piece of clothing he didn't like before but now feels it's the perfect fit. He tries to connect this with his ex-girlfriends whom he broke up with — not a good match at that time, but could one of them be the one? Soon he zooms on Natalie who was serious about the relationship but he didn't feel like settling down. He convinces Natalie to get back together. When he dumps her again, she beats him up and the shirt gets absolutely ruined.
- A Birthday, Not a Break: Natalie has to suffer a breakup with her boyfriend Ted on her birthday. Twice. Ted is not even aware that it was her birthday. Twice.
- The first time he breaks up with her by leaving a message on her answering machine, which is played in front of everyone at her surprise birthday party. She is devastated.
- The second time, Ted breaks up with Natalie publicly in a fancy restaurant, again not even being aware that it's her birthday. Natalie uses her Krav Maga skills to beat him up.
- Birthday Party Goes Wrong: Ted says he broke up with his girlfriend Natalie over an answering machine right before her birthday. It's revealed it was on her actual birthday and she was having a surprise party. All her friends heard Ted's embarrassing voicemail. After several years, Natalie is still bitter about it.
- Butt-Monkey: Natalie gets dumped by Ted on her birthday in front of many people. Twice. Once at a surprise party in front of their friends, second time in a fancy restaurant.
- Chekhov's Skill: Natalie's Krav-Maga lesson becomes useful... in kicking Ted's ass.
- Comically Missing the Point:
- Ted's kids, after he tells them the story of when he dated an ex, who he had previously dumped on her birthday, via an answering machine message, convinced her that he'd changed in order to get a second chance, only to break up with her on her birthday AGAIN, only this time in person... Which led to her kicking Ted's ass. All Ted's kids took from this story is that their dad got beat up by a girl.
- Ted is focused on missing a party and being kept out of the secret instead of the fact that he hurt Natalie a lot.Ted: There was a surprise party that night? And nobody told me? People don't think I can keep a secret, but I totally can! [Beat] Not the point.
- Barney absolutely ignores the fact that Ted wants to get back with his ex-girlfriend and fixates on one particular detail of Ted's stories about his other exes.Ted: Maybe I should call [Natalie]. What do you guys think?Barney: You dumped a porn star?! Friendship over. FRIENDSHIP OVER!!!
- Dumped via Text Message: Ted broke up with his girlfriend Natalie over an answering machine. Worse, it was right before her birthday — eventually revealed to have been on her actual birthday while she was having a surprise party. All her friends heard Ted's Embarrassing Voicemail.
- From Bad to Worse: Ted's story of breaking up with Natalie. On her birthday. To her answering machine. In front of all her friends. Ruining a surprise party. His confession to Lily involves False Reassurance, Exact Words and Digging Yourself Deeper.Lily: So, you dumped her right before her birthday?!Ted: No! I didn't dump her right before her birthday...Marshall: [Oh, Crap!] ...uh oh...
- Freudian Slip: Invoked. Barney dares Robin to say a nipple on TV for some money. She does so, but inserts it in a sentence to make it appear accidental: The first hot dog cart's hot dogs originally cost a nipple.Barney: Hey, is it cold in here, because I can kind of see Robin’s nickels?
- History Repeats: Ted dumps Natalie on her birthday for a second time.
- Humiliation Conga:
- Ted and Natalie's first breakup happened during the latter's surprise party three years ago with Ted breaking up with her over the phone which her family and friends heard through the answering machine.
- Robin falling into horse poop on live TV. Which the whole bar she frequents saw.
- Instant Humiliation Just Add Youtube: While YouTube is not mentioned, since it was relatively new and semi-unknown at the time, the video of Robin falling on horse crap had been posted online, giving instant humiliation to Robin.
- Laser-Guided Karma: Robin spends most of the episode bastardizing her job by saying dirty things on the air. By the episode's end, she fell on a literal crap. Horse crap.
- Limited Wardrobe: Ted wears the titular shirt throughout the episode. Lampshaded by Lily:Lily: Nice shirt, Ted! Is it yesterday already?
- Mood Whiplash: Courtesy of Barney's promise of $200:Robin: (reporting from a house) An occasion that was supposed to be joyous suddenly turned tragic when Ethel and Sadie Margolis, New York's oldest twins, suddenly passed away on this, the eve of their 100th birthday. I'm a dirty, dirty girl. (slaps ass) Ow. Reporting live, Robin Scherbatsky, Metro News 1.
- My Girl Is a Slut: The first of Ted's ex-girlfriend prospects made 175 porn movies in a month.
- No Sparks: Ted's reason for breaking up with Natalie the second time. He likes her well enough, but she's not the one.
- Rule of Three: Marshall and Lily reviews two ex-girlfriends of Ted before they mentioned Natalie.
- Smug Snake: Robin's attitude towards her job by accepting Barney's bet easily comes off as "If you don't give me my break, then I'm going to keep screwing around".
- The Sociopath: The second of Ted's ex-girlfriend prospects casually talked about running over a hitchhiker when she was 16.
- Surprise Party: In a flashback, we see Natalie's family and friends threw her a surprise birthday party. Notably, her boyfriend wasn't invited because he had a reputation of not being able to keep a secret. He spoiled the party by dumping Natalie over her answering machine right before Natalie's arrival. Ted is the jerk in this story and he was only vaguely aware her birthday was coming up.
- That Came Out Wrong: Everything Ted says to let Natalie down easy goes this way. He says that the reason he doesn't feel any sparks is "ineffable"; she mishears this as him saying she's "not 'F'-able". He says their not working out is like they lost the lottery (something that's so likely to happen, they shouldn't take it personally); she takes it to mean that he thinks dating him is like winning the lottery.
- Woman Scorned: Ted has broken up with Natalie is a particularly nasty way. Then he convinces her to get back together... only to break up with her once again. On her birthday. Natalie has all the right in the world to be angry, especially since once he knew it was her birthday there was no reason he couldn't have postponed breaking up with her by at least a day or two. She beats him up in the restaurant and humiliates him in front of many people.
