When its possible Ted might not get the job of his dreams due to being late to arrive for a flight, he traces back when bad things started happening to him and the blame is passed on from every member of the group.
This episode provides examples of:
- Bittersweet Ending: Ted and Robin miss the flight to Chicago, meaning he loses his dream job. However, he says that if he hadn't stayed in New York, he wouldn't have met the Mother.
- Call-Back:
- The titular penny is the one that Ted found back in "The Scorpion and the Toad". In the flashback of him and Robin in the bar, their outfits are from that episode.
- Barney's gambling addiction is brought up again before Marshall restricted the bet to 50 dollars.
- Didn't Think This Through:
- Ted hopes that a penny from 1939 is worth enough to pay for dinner. 150 times worth of a penny is only $1.50, though it has appreciated in value.
- Ted attempts to jump a turnstile to help Barney from a subway. This leads to him getting arrested and sentenced in court.
- Disaster Dominoes: Ted concludes that he lost his plane to Chicago, preventing him from getting his dream job.
- It starts with him finding an antique penny.
- He invites Robin for hot dogs with the money he got from the penny, spotting a bridal boutique on the way home.
- This makes Lily and Robin camp there, after which Robin had to crash at the apartment and causes Marshall to break his toe.
- Marshall's accident initiates a bet with Barney that he can't run the marathon without training.
- Finishing the marathon granted him free use of the subway train, and Barney gets paralyzed in the subway, literally unable to leave the train.
- Ted, trying to rescue him, ended up trespassing on the metro and be cited to court on the day of the flight.
- In the end, it all turned out to be crucial, because staying in New York prevented Ted from moving to Chicago, which eventually allowed him to meet The Mother.
- Foreshadowing: Ted attributes the Lucky Penny for keeping him in New York and eventually meeting The Mother. Years later, he reveals that he named his daughter "Penny".
- For Want Of A Nail: Ted concludes that if he hadn't picked up that lucky penny, he wouldn't have missed his flight.
- From Bad to Worse: After Barney's legs give out on the subway, a series of passengers come up to him, seemingly needing a seat in the crowded subway more than him. In order, it's a pregnant woman, an old lady, and a young boy on crutches, each of whom make Barney look increasingly worse for appearing to selfishly refuse to give up his seat.
- Hard Work Hardly Works: Subverted. Marshall is disappointed that his months-long training is "wasted" since a broken toe means he can't run in the New York Marathon. Barney on a whim volunteers to run in his place without any training, betting 50 dollars. He actually manages it, astonishing his friends. Then Barney's body gives out on the subway, which Marshall says was worth the money.
- Heh Heh, You Said "X": Robin gets a kick out of Lily saying Vera Wang.
- Heroic RRoD: Barney runs a marathon without training for the endurance or stamina to complete all 26.2 miles. While he is able to complete it since he's in above average physical condition, his body completely gives out from the effort a few hours later.
- How We Got Here: Robin and Ted trace the events that led to them missing the flight.
- Humiliation Conga: After mocking Marshall and finishing the marathon without training, Barney couldn't move his legs and couldn't leave the train. This led to him unable to give his seat to a pregnant lady, an old woman and a kid with a cast, and getting mugged by the end of the episode.
- Missed the Bus: Ted misses a plane to Chicago for a super-important job interview. He thought it was his destiny to make it and get his dream job. He and Robin contemplate what led to them missing that flight. Had Ted gotten that job, he would have had to eventually relocate to Chicago. This way, he stayed in New York and later met his future wife.
- Necessary Fail: Ted needed to miss his dream job or else he would have had to move to Chicago and never met The Mother.
- Never Heard That One Before: One of the flight attendants who helps Ted and Robin asks her if the pizzas from one broadcast were real. She mentions that they weren't and that other people have asked about it.
- Pursue the Dream Job: Ted already works as an architect, which he loves and considers his dream job, and in this episode he is being headhunted by people who want him to run their entire office. This would be another big step in his dream career.
- Noodle Incident: Somehow Barney gave the whole gang a rash at Christmastime.
- Not What It Looks Like: Robin walks in on Marshall rubbing his nipples and giving himself a pep talk.
- Ticket-Line Campout: Lily and Robin join a line for a massive sale at a bridal shop. The entire line is driven to madness when a car alarm goes off and blares through the night. When the owner shows up in the morning the irate brides-to-be start throwing things at him in revenge.
- Training Montage: Of Marshall working out for the marathon.
- Worth It: After finding out that Barney got paralyzed at the subway after running the marathon without training, Marshall didn't regret betting his 50 dollars for this.
