- Connie: Wow, it looks like the postal service has been slacking off.
Steven: Jamie's the only mailman who knows where I live.
Garnet walks out of the sea, returning from her search at the bottom of the ocean for Jasper and Lapis. Jamie is instantly smitten. Garnet tells Steven that she didn't have any luck finding either of the two Gems, and after insta-drying herself, she walks off.
Later, Steven and Connie go through all of Steven's packages and find many packages of Sea Pals. Steven tells Connie that when his initial order of Sea Pals didn't arrive, he kept ordering more. After Steven tells Connie he wants to set all the Sea Pals free into the ocean, Jamie comes up to them and, stammering and blushing, delivers a pink envelope sealed with a heart-shaped seal. He runs off before Steven can ask what the envelope is, but Steven and Connie notice the "FOR GARNET" penciled on the front of the envelope.
Steven and Connie run inside the house and read the letter to Garnet. While Steven is reading the letter, the scene flashes to Jamie writing the letter in Shakespearian get-up, with a large white quill, in a room lit by candlelight. After Steven finishes reading the letter, Connie concludes that Jamie is asking Garnet out on a date! Steven then tells Connie that will not be happening, since Garnet is a relationship between Sapphire and Ruby.
Connie then insists that they write a letter in response since Jamie put so much thought into his letter. She has Garnet dictate what she should write, but the resulting letter ends up rather...harsh.
- Dearest Jamie,
And even after that.
Connie then concedes that at least it's to the point, and Steven and Connie run off to give the letter to Jamie. They find him sitting and staring out into the ocean, and they sit next to him to try and give him the letter. He then starts describing why he's staring into the ocean before they can say anything. Apparently, Jamie got rejected over and over again as he went from audition to audition in Kansas. He returned back to Beach City because he couldn't bear another rejection. Steven and Connie then decide it would be best not to give the letter to Jamie, since it would just make him more upset.
Back at Steven's house, Connie and Steven write up a nicer letter to let Jamie down easy. Satisfied with what they wrote, they place the letter in the mailbox for Jamie to pick up.
However, that night, Steven is interrupted when playing his video games by Jamie yelling outside the balcony for Garnet. Steven realizes that Jamie completely misinterpreted the letter Steven and Connie wrote and thought it meant that Garnet reciprocated his feelings. Steven tries to correct him, but is interrupted by Jamie when he notices Garnet walking up next to Steven.
- Jamie: Ah, Garnet! You've come! You can tell Steven about all the beautiful things you wrote to me in this message!
Garnet: (confused) I didn't write that!
Steven reluctantly admits that he and Connie wrote that letter to let Jamie down gently. When Jamie asks Garnet if this is true, Garnet tells him that she does not and never will want to be in a relationship with him. Jamie runs off in tears.
The next morning, Steven tells Connie he feels awful about Jamie, but Connie reassures that Jamie will bounce back from this and will probably be here soon to deliver mail like he always does. A postwoman with short, blond hair then asks for the location of the home of Steven Universe. Steven runs over to her and tells her that he is the home of Steven Universe. The postwoman tells him that she thought Jamie was joking when he said that this is where Steven lived. When Steven asks where Jamie is, the postwoman tells him that he was too emotionally crushed from having his love spurned to resume his normal route. She chuckles at Jamie's dramatics, gives Steven a coupon book, and tells him to have a nice day.
Garnet then leaps out of the ocean punching a gem monster. After hurling it back, she notices Steven and Connie's sad looks. Steven and Connie tell her that Jamie is crushed and that it's all their fault. Garnet tells the two that she'll talk to Jamie, but the two try to convince her not to since her words will destroy him.
Jamie is sitting on the beach, melodramatically lamenting his rejection (punctuating his speech by hurling a fistful envelopes into the air and watching them flutter into the ocean). Garnet finds Jamie, sits next to him, and tells him she didn't mean to make him so upset. Jamie then asks if she'll go out with him, but Garnet rejects his offer again. Jamie insists that he loves her, but Garnet tells him that Love at First Sight doesn't actually exist, since, to love a person, you have to actually know them, and Jamie doesn't even know who — or what — she is. She then tells him that he's a very convincing actor, since his performance of the lovesick fool convinced Steven and Connie, and convinced himself, too, and advises him to try local theatre.
Garnet leaves, and Steven and Connie sit next to Jamie and ask if he is okay. Jamie tells them that Garnet gave him some pretty solid advice. Steven then asks if all the letters in the water were from him to Garnet, but Jamie says that they were actually the mail he was supposed to deliver on his last round. Steven and Connie offer their help to collect them and Jamie accepts it.
- Absentee Actor: Pearl and Amethyst don't appear.
- All There in the Script: The postwoman's name is Barb, and she's Sadie's mom.
- Alternate History: Given how seriously Connie and Steven take Jamie's claim of trying to find acting fame in Kansas, it's possible their timeline doesn't have California as the center of the entertainment industry. Or they were just being polite.
- An Aesop:
Garnet: "Love takes time, and love takes work...At the very least you have to know the other person."
- Garnet's advice to Jamie at the end.
- Sometimes it's better to be straightforward with people or you'll give them the wrong idea.
- Just because someone is interested in you, you have no obligation towards them and you can reject them.
- Animesque: Jamie turns his face into this when calling for Garnet.
- Bait-and-Switch: Jamie tells Steven and Connie he went to make it big in the entertainment industry... in Kansas.
- Believing Their Own Lies: Garnet says that Jamie played the lovesick fool so well he even convinced himself.
- Blunt No: Reconstructed. Garnet's face-to-face rejection hurts Jamie's feelings, later prompting her to apologize for her curtness. But her steadfastness to her answer does help Jamie come to terms that she's not into him.
- Broken Aesop: Love at First Sight doesn't exist and love takes time and work... unless you're Rose and Greg.
- "We Need To Talk" acknowledges that Rose and Greg were not exactly perfect right off the bat, and needed time to really understand each other.
- Brutal Honesty: Garnet's reply letter to Jamie, which is originally just the word "no", but is later expanded to be even more blunt. Lampshaded by Connie.
- Call-Back: Steven tells Connie about Ruby and Sapphire. Garnet being a relationship is one reason why she doesn't want to date Jamie.
- Continuity Nod:
- Steven mentions setting plants he grows free.
- Garnet first appears in the episode coming out of the sea after looking for Jasper and Lapis.
- Garnet's swim goggles from "Giant Woman" make a reappearance. Here, it's shown that she wears them over her usual Cool Shades.
- Connie knows about fusion and what it represents; after all, she fused with Steven in "Alone Together".
- Cool Shades: Jamie is first seen with a pair that he brought in a souvenir shop in Kansas and have written "Movie Star" on the lenses.
- Crush Blush: Jamie has this around Garnet or whenever he thinks about her. Noticeably, Steven has this for a moment when taking selfies with Connie.
- Crush Filter: A Gaussian Girl effect surrounds Garnet when Jamie sees her for the first time.
- Drama Queen: Being an amateur actor, Jamie has a bad habit of getting into the "Drama Zone" a little too often.
- Early-Bird Cameo: Jamie the mailman made his first appearance all the way back in "Cheeseburger Backpack".
- Barb the postwoman (who's also Sadie's mom) briefly appeared in a crowd scene next to her daughter in "The Return".
- Hidden Depths:
- Jamie wants to be an actor, and Garnet seems to think he has some talent.
- Garnet actually gives really good love advice, despite her seemly distant behaviour, in virtue of being a relationship.
- Hopeless Suitor: Jamie tries to ask Garnet out, unaware that she's already a relationship (in other words, a semi-permanent fusion between two Gems), which is lampshaded.Steven: Well, that ain't happening.
- Implied Death Threat: Ronaldo assumes his letter to be this, since most of the words are barely readable.
- Innocently Insensitive: Garnet's extreme bluntness and initial lack of any attempt to let Jamie down easy come across as this when, after realizing how upset he was, she finally relented of her cold manner towards him. After she realized that her bluntness and refusal to discuss it were upsetting, she sat down with Jamie and calmly explained that since he didn't really know anything about her at all, he wasn't really in love with her but rather with an idealized figment of his imagination, and concluded by complimenting his acting skills to try to cheer him up.
- Knuckle Cracking: Steven cracks his knuckles before getting to work, but it makes no sound.Connie: Your knuckles are so quiet.
Steven: My hands are polite.
- Lampshade Hanging:
- The lack of mail Steven's had is mentioned; apparently, only Jamie knows where he lives among the postal staff.
- Connie notes how quiet Steven's Knuckle Cracking is.
- Large Ham: Jamie gets pretty hammy, especially when trying to woo Garnet.
- Laser-Guided Amnesia: Discussed. Steven asks to Garnet if she could just zap Jamie's brain to make him forget all about his feelings for her.
- Love at First Sight: Jamie's crush on Garnet. Garnet actually defies this trope, saying love takes time and work and that love at first sight doesn't even exist.
- Love Letter: The title. Jamie wants to give one to Garnet.
- Love Letter Lunacy: Steven and Connie write a gentler rejection for Jamie instead of giving him Garnet's. He thinks the letter has some mixed messages and convinces himself she reciprocates his affections.
- Loving a Shadow: Garnet considers Jamie's love to be this since he doesn't know her at all.
- Metaphorgotten: Jamie's letter brutally tortures more than one metaphor.
- Nice Job Breaking It, Hero!: Steven and Connie try to let Jamie down easy instead of giving him Garnet's Brutal Honesty letter, but give him the wrong idea entirely.
- O.O.C. Is Serious Business: When the usually Stoic Garnet suddenly goes full-on Sassy Black Woman, you know it's for real.
- Poor Communication Kills: Steven and Connie's attempt to let Jamie down gently causes him to misinterpret things and think Garnet is interested.
- Purple Prose: Jamie's letter. Lampshaded when he's shown writing it with a feather quill by candlelight, while dressed in an outfit and seated in a room that would both make a 16th century nobleman proud. The letter Connie writes back is hardly any better — she styled it after a soap opera.
- Official Couple: In case "Jailbreak" wasn't clear enough with its message, this episode makes sure to cement the idea of Ruby and Sapphire being exclusive.
- Reality Ensues: Two of them, simultaneously from the letter alone.
- Sexy Walk: Garnet, while she comes out of the ocean. Or maybe it's all in Jamie's head.
- Shipper on Deck: Jamie says Steven and Connie look cute together.
- Ship Sinking: This episode seems to torpedo a potential relationship for Garnet, not just with Jamie, but with anybody.Garnet: Three's a crowd.
- Ship Tease: Connie and Steven trying to take a selfie at the beginning.
- Strong Family Resemblance: Barb looks similar to her daughter, Sadie.
- Taught by Television: Connie is convinced she can fabricate a Purple Prose letter to Jamie because she's watched soap operas. It doesn't go so well.