The gang is confused as to how their last meeting with The Captain went down, and Lily's the only one with a reliable story.
This episode provides examples of:
- Accidental Misnaming: The Captain called the gang because he wanted to speak to "Robin", which leads Robin to think she did seduce him while drunk. Actually, The Captain confused her for Lily.
- Ambiguously Bi: Barney brings up the possibility of being in a three way with another guy just to see what it's like.
- Attention Whore: Barney kept insisting that he was with Lily, Ted and Robin at the Art Gallery, even though he wasn't. After Barney expressed his disappointment for not being in the story and part of their group adventures, the others pretend that they have forgotten him there pulling one of this Playbook tactics. Then it's confirmed that he was really there, as Barney was the reason The Captain's previous art consultant was absent for the end of the flashback story.
- Audience Surrogate: The others are telling the story to Marshall, who was the only one absent at the time, while Barney kept insisting he was there as well.
- Brick Joke: The Captain says his original art consultant quit after meeting an archduke at the gallery, revealing that Barney really was there the whole time.
- The Bus Came Back: After being absent following "Garbage Island", The Captain finally comes back after two seasons.
- Call-Back: Lily reveals that she stole The Captain's crystal ashtray because he was rude to her after she praised a painting he didn't like. This is tied to her "Aldrin Justice".
- Continuity Nod:
- The Gang keeps referring to Becky as "Boats, Boats, Boats!" Girl.
- Ted remembers that the last time he and The Captain talked to each other was after he stole Zoey away from him and still feels guilty about it.
- Ted also says that he tried a second date with Becky while "eating sandwiches".
- Easily Forgiven: The Captain no longer holds any resentment towards Ted after his divorce from Zoey, but Ted is still afraid of him.
- Foreshadowing: Ted thinks that The Captain is mad at him because he had a picture of Becky on his desk, afraid that he unintentionally is stealing another woman from him. The real flashback shows that said picture was actually a promotional photo of one of the boats from Becky's commercial. But then forward to Season 9 we find out that Becky and The Captain did marry.
- Heroic BSoD: Lily has been upset at how her career has gone against her lifelong dream of being an artist after The Captain dismissed her as "just a kindergarten teacher". She snaps out of it when The Captain admitted he was wrong and hires her.
- Hunting the Most Dangerous Game: Ted muses that The Captain is rich enough to have a private island in the Caribbean where he hunts people.
- MacGuffin Title: The episode is named "The Ashtray" because during the second act, The Captain called and Lily thought it was because she stole his crystal ashtray a year ago. It turns out that The Captain didn't even notice that it was missing and the reason he called was completely unrelated to that.
- Once More, with Clarity: The story of the evening with The Captain gets told by Ted (with interruptions by Barney), retold by Robin (with interruptions by Barney), then reretold by Lily (with interruptions by Barney).
- Spot the Thread:
- In both Ted and Robin's recollection of what went on at the Captain's home, Ted was (seemingly) being confronted by him in the living room; he even shouts in fear. But, in Lily's recollection, Ted shouted in fear... while the Captain was with Lily, in a different room. And then you factor in the reveal of The Stinger...
- When Lily meets up with the Captain to return his ashtray, he reveals his previous art consultant quit after meeting an archduke at the museum. The Stinger shows us one of Barney's plays... called "The Royal Archduke of Grand Fenwick"...
- The Stinger: "The Royal Archduke of Grand Fenwick". If you needed concrete proof Barney was with the gang that night...
- Twist Ending: After thinking the entire episode that The Captain was upset at one of them, it turns out that he wanted Lily to work for him as his new art consultant.
- Unreliable Narrator: Turns out Ted and Robin's versions of the story can't be trusted. Ted was high and Robin was drunk.
