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Derek, the guy who mentioned his move for 847 consecutive daysDerek got a job offer in Austin nine months ago. He spent the first month telling everyone. Then the second month. Then he started calculating how many barbecue restaurants he could visit before moving. Derek has said 'well, I'm heading to Texas soon' so many times that people started replying with just a thumbs-up emoji. Derek, Texas has your moving announcement printed on billboards now.
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Patricia, HR manager, packer of industrial organizational systemsPatricia labeled every box with a laminated, color-coded system. She created a spreadsheet tracking which kitchen towels were 'essentials' and which were 'sentimental.' Patricia actually printed the spreadsheet and taped it to her moving truck. Patricia, the movers are supposed to help you move, not audit your life choices.
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James, the 'definitely staying in touch' guyJames promised he'd be back in town every month. He said the distance wouldn't change anything, that he had a standing Thursday night game reservation with the guys, that he was only three hours away so no big deal. James moved to Portland. James texted the group chat once from a coffee shop three months later. James, your definition of 'staying close' is now a strongly worded Instagram follow.
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Linda, retiring librarian, scrapbooker of memoriesLinda spent two weeks making a photo album of her time in the office. She laminated photos, added captions in calligraphy, organized them chronologically. Linda presented it at her going-away party like it was the Dead Sea Scrolls. Linda, most people just accept a Starbucks gift card and call it a day.
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Marcus, the guy moving back to his hometownMarcus moved to the city fifteen years ago for a job. Now he's moving back home because he 'missed the simple life.' Marcus has spent the last six months romanticizing his childhood, forgetting that his hometown has seventeen people and one stoplight. Marcus is going to be calling his real estate agent by October.
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Ellen, the relocation expert with seventeen moving companiesEllen got three quotes. Then seven more. Then she called moving companies she'd already called to verify their estimates. Ellen created a comparison matrix. Ellen had opinions about truck sizes and insurance options that could fill a seminar. Ellen, you're moving to the suburbs, not relocating the Smithsonian.
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Robert, the guy discovering winter for the first timeRobert is moving from Los Angeles to Minneapolis. He bought a parka three months early. He's been watching YouTube videos about snow removal. Robert bought a shovel and stored it in his apartment. Robert has asked everyone 'but what about the cold?' with the tone of someone asking about surviving a blizzard. Robert, welcome to the Midwest. Bring layers and lower expectations.
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Susan, the coworker who's transferring to 'find herself'Susan decided she needed a fresh start. She's quitting the corporate job and moving to Portland to be a 'creative.' Susan has already bought a vintage bicycle she can't ride and followed seven wellness influencers. Susan is going to realize in six months that moving solves nothing and that finding yourself usually just means finding a different Starbucks.
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David, the guy who's been 'planning this for years'David finally got his down payment saved. He's been talking about leaving since 2019. David now has a house in the suburbs with a mortgage that will keep him awake at night. David's farewell speech involved a lot of talk about 'life chapters' and 'new adventures.' David, that chapter has a 7-percent interest rate and a thirty-year commitment.
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Nancy, the office manager documenting every stepNancy created a thirty-page transition document. She labeled every file, updated the shared drive with seven levels of folders, and left seventeen sticky notes on the desk. Nancy even categorized the office supplies by priority and preference. Nancy has somehow made leaving feel like a Fortune 500 handoff. Nancy, the next person's first task is recycling your documentation.
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Karen, the executive assistant changing time zonesKaren has been running everyone's schedule for twelve years. She knows which meetings are actually important and which ones are just people avoiding work. Karen has already color-coded her new office setup before she's even arrived. Karen is going to spend the first month explaining to her new team why she keeps trying to optimize their calendars. Karen, let people be inefficient. It's called culture.
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Andrew, the guy with a truck bed full of mistakesAndrew is convinced he can move himself. He rented a truck and convinced four friends to help with the promise of pizza and 'it'll only take a few hours.' Andrew has no idea how to use a dolly. Andrew's idea of packing is throwing things in boxes and hoping for the best. Andrew's friends are already regretting their decision. Andrew, this is why professional movers exist.
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Brenda, the emotional leaverBrenda has cried in three separate meetings about how much she'll miss everyone. She's given handwritten thank-you cards to the entire office. Brenda is treating this like she's leaving for a decade-long mission to Antarctica instead of driving four hours to a new job. Brenda has promised to call, text, email, and write actual letters to stay connected. Brenda, take a Dramamine before the goodbye lunch. This is already intense.
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Rick, the guy with a meticulously planned routeRick planned his move with military precision. He mapped the exact route, calculated travel time, and identified rest stops. Rick has backup routes in case of traffic. Rick has researched the neighborhoods like he's doing a doctoral dissertation. Rick packed his U-Haul with the organization of someone loading a spacecraft. Rick, sometimes you just throw things in the back and hope.
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Michelle, trading city for coastMichelle got tired of the urban grind and is moving to the beach. She's already talked about learning to surf, spending mornings on the sand, and living a 'simpler life.' Michelle seems to think that moving to the coast automatically makes a person into a serene yoga instructor. Michelle is moving in July when the tourist season is in full swing. Michelle is going to miss the anonymity of crowds within three months.
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George, the guy leaving for the quietGeorge is escaping the city noise and moving to the countryside. He's talked about enjoying the peace, the stars, the open space. George seems unaware that rural areas have roosters, and roosters don't respect sleep schedules. George has bought three coffee table books about rural living but has never actually spent a winter away from a grocery store. George, farms are loud and inconvenient.
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Jennifer, the job-hopper's farewellJennifer is leaving for the third new job in five years. She talks about this one being 'different' and 'finally the right fit.' Jennifer has said this about the last two jobs. Jennifer has already decided she'll be here eighteen months before the next opportunity comes along. Jennifer is going to realize that running away from problems just means meeting them in a different conference room.
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Carol, the memory keeperCarol took a group photo every single week for the entire month leading up to her departure. She wants memories of memories. Carol is building a photo library like she won't ever have another job or friend group. Carol probably has three thousand photos on her phone from this office already. Carol, people will remember you without photographic evidence from every Tuesday.
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Frank, the guy with practical advice nobody asked forFrank has been offering relocation tips to everyone who will listen. He talks about the best moving companies, the right time of day to move, weather patterns by region. Frank seems to think leaving the area requires a PhD in logistics. Frank will corner people in the break room to discuss his moving philosophy. Frank, people just want to say goodbye. They don't want a TED talk about truck rentals.
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Diane, planning the grand exitDiane wants her last day to be a full celebration. She's organized a catered lunch, a group dinner, drinks after work, and a brunch the next morning. Diane is treating her departure like she's a retiring president. Diane hasn't considered that most people have plans on those days or that saying goodbye once is probably enough. Diane's last week is going to be more exhausting than her first week was.
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Tim, the guy moving for loveTim is relocating because he met someone online and they're finally making it official. Tim has never actually visited this person's city. Tim has built up an entire fantasy about what living together will be like. Tim's friends are cautiously optimistic and also taking bets on how long this lasts. Tim, moving for love is romantic until month two when you discover incompatible breakfast preferences.
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Helen, the one-last-project personHelen has decided to completely finish every project before she leaves. She's taking on extra work in her final weeks. Helen is going to work herself into exhaustion so the next person doesn't have to deal with loose ends. Helen seems unaware that this is literally the next person's job. Helen, leaving things for other people to finish is called 'transition planning.'
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Valerie, the guilt-tripperValerie is leaving and making everyone feel terrible about staying. She keeps saying how they're 'trapped' and she's 'finally free.' She talks about how brave she is to leave everything behind. Valerie seems to think that staying at a job means settling for less. Valerie is making everyone's career choices feel inadequate. Valerie, you can leave without making everyone else feel small.
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Irving, the guy who's moving back in with his parentsIrving is thirty-four and moving back in with his parents to 'save money for a house.' He talks about how it's financially smart and how his parents have a basement apartment that's 'basically his own place.' Irving seems to have forgotten what it's like to live with his mother checking on him constantly. Irving is going to last six months before he's paying for his own apartment again just for privacy.
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Sophie, the future pen palSophie is moving to take an extended sabbatical abroad. She's planned a whole itinerary and talked about how she's 'going to find herself' and 'experience the world.' Sophie has bought a fancy planner for her travels. Sophie has probably already bought a subscription to some journaling app. Sophie is going to post beautifully filtered photos for three weeks, then stop updating entirely.
Three rules for a going-away roast that actually lands.
Lean on the move story.
The decision, the eight months of "I'm definitely doing it," the spreadsheet of moving companies, the goodbye that never quite happens.
The leaver isn't the only target.
The friends/coworkers reacting are good material too. The denial, the staged grief, the "we'll definitely visit."
End on the truth.
The room is sad they're going. The roast earns the toast. Make sure they leave knowing they were loved.
Frequently Asked Questions
How do I write a funny roast for someone who's leaving?
Focus on one specific habit or quirk they're known for, then exaggerate it lovingly. The best roasts land because everyone in the room recognizes the person immediately. Make sure the punchline is something they'd find funny too, not a genuine criticism wrapped in a joke.
Should I mention where they're going?
Only if it's part of the joke. A roast about moving to the suburbs is stronger than a roast about the person themselves. If the location matters to the humor, use it. If it's just context, skip it and roast the person instead.
How long should a going-away roast speech be?
Two to four minutes is perfect. Long enough to tell a real story and land three solid jokes, short enough that you leave the room wanting more instead of checking their watches.
Is it okay to roast someone who's sad about leaving?
Yes, but adjust the tone. A person who's reluctant to leave needs affection-first humor that acknowledges the sadness while still landing the laugh. The roast becomes 'we love you and we're sad too, but also look at this funny thing about you.'