How to Write a Cover Letter in 2025
A detailed guide
Step 1: Look at the job description and realize it’s written by ChatGPT. Though you are applying for a copywriter position and you have previously fought hard against ChatGPT, fearing that it would come for your job, you consider firing up the ol’ ChatGPT dream machine so that one robot can ostensibly seduce another robot. It’s time robots endured the pain of online dating. Why should they get your best if they’re not coming with theirs?
Step 2: Realize that your supposed “best” is going toward your pilot script. The one you were so excited about when it was a logline that you told your writing class. Now that it’s in its second draft, it sucks. You wonder if when you watch a TV show, you are simply opening your mouth like people do when they’re snoring: not fully breathing it in and exhaling sounds no one wants to hear via your script.
Step 3: Scroll LinkedIn. This is the most depressing activity you do on a daily basis, and you are someone who plays Bus Jam on a daily basis, so that’s saying something. LinkedIn is such a hellscape of hollow congratulatory statements, bloated posts stuffed with buzzwords and fake excitement, and someone you once shared a joint with celebrating 10 years at “comedian.” You start to play one of the LinkedIn games, then realize that is actually the most depressing activity you do on a daily basis.
Step 4: Check your email. Senators would like you to donate money. You don’t have any money to donate, so you search “how to help fight Trump.” Many progressive websites reiterate that life is bleak, and that it’s important to stay informed. You search “how to take action to fight Trump in my community.” It takes you to a site to donate money.
Step 5: Check jobs that are recommended for you on LinkedIn. It says you should manage a Whole Foods 20 miles away. You have no retail experience and none of the qualifications align with yours, but LinkedIn says it’s a great match.
Step 6: Start making cookies. You can take them to your friend’s party you’re going to tomorrow. Or you can eat them slowly throughout the day as a reward for every small task.
Step 7: Make the bed while listening to a podcast about perimenopause. Perimenopause is so hot right now.
Step 8: Think about how you haven’t gotten a pap smear in awhile. You’re not craving one or anything, but you should probably look into that. It would be a lot easier if your Covered California insurance wasn’t so expensive that it forced you into an HMO plan. An HMO plan that Covered California accidentally canceled, so you were sent a comprehensive bill for a mammogram, which you’re refusing to pay on principle. Both your insurance provider, Anthem, and Covered California are blaming each other for the gaffe. Your last conversation with the doctor assigned to you was completely unhelpful and you actually had to correct them on a medical fact. Your doctor replied “Oh, yeah. You’re probably right.” What’s wild is that this is somehow the best version of affordable insurance we’ve had in awhile that didn’t come from an employer. You wonder how the fuck other countries have the free healthcare thing so dialed in, but our country is too greedy to ever do that. You search how to help simplify healthcare access. It takes you to a site to donate money.
Step 9: Eat a cookie as soon as it comes out of the oven as a reward for making the bed. Suffer a tongue burn that will remind you how desperate you were for a cookie for the rest of the week.
Step 10: Consider the blank page where your cover letter should go. You give ChatGPT a whirl. It writes something perfectly bland. You think about that time you got a C+ on a paper for being “overwrought.” You tell ChatGPT to write your cover letter with overwrought sentences. It sounds exactly like you did in college.
Step 11: TikTok break. Your algorithm has been hot recently. It’s funny and/or shows you a lot of videos of Walton Goggins. You are attracted to Walton Goggins. This is perplexing and weird. So unlike your normal type. You text your group chat you’re attracted to Walton Goggins. One of your old friends responds “checks out.” Oh.
Step 12: Your dog is crying. He cries all the time now. It’s actually been awhile since you cried. The last time you cried was… Perhaps it is sadder you can’t remember. He cries and cries and then cuddles up with you. Cute! Then, he starts licking his asshole on your arm. You say “STOP IT!” and let him outside. He sunbathes. He is happy. You think about going outside, but say no because you have so much work to do.
Step 13: You remember the last time you cried. It was at “Dìdi.” That was a great coming of age movie. You search how old the filmmaker Sean Wang is. His Wikipedia says he was born in “1994 or 1995.” Either way, that’s younger than your ass.
Step 14: One of your tabs that’s perpetually open is the Warped Tour lineup. You have tickets. The lineup is okay, but you refresh it every day because 13 bands have still not been announced. 311 has been announced, and you secretly think this will be very fun to see live. You keep joking with your friends about how 311 is on the lineup, but you’re truly so excited to see 311. You might even cry at 311. You cried at My Chemical Romance. You cried at the last concert you went to and turned to your husband and said “Live music is so moving!” You were going through it, but honestly live music is moving. And healing! You think about you might actually need Warped Tour to survive.
Step 15: Check your texts and realize your group chats are popping off. You remember that Today, Explained podcast you listened to about how one person in a couple is the “group chat person” and one member is the “real job person.” You think of how you told your husband you used to get in trouble for writing notes in class all the time and he said “wow, you’ve been group chatting all day since before group chatting all day existed.”
Step 16: Check your Substack stats. Why did three people unsubscribe since you started it? Do they think you’re overwrought? Why aren’t more people subscribing? Don’t they know you’re writing quality shit out here?
Step 17: Delete ChatGPT’s version of the cover letter and go to your Google doc that has all of your self-written cover letters you vacillate between. “Wow, these are garbage,” you think. “But will anyone actually read it?” You think of sneaking in some sort of test to see if people read them. Some sort of “if you’re actually reading this, just send me a sign.” You wonder if "The New Yorker” would like something like that. Would you be as famous as Joel Stein, who also got to be on “I Love the Decades”? Or at least Hawk Tuah girl? Should you get into crypto?
Step 18: Dance break! You love the new Chappell Roan song. You hate how Chappell Roan sounds in interviews. You wonder if that makes you old. What does Sean Wang think? Wait, is he also considered old?
Step 19: Remember how you heard about women making money from selling their feet shavings. And pictures of their feet. And their used underwear and socks. How are you so stupid you have not considered these avenues? You could have bought a house by now if you were not so precious about keeping your worn underwear to be washed and worn again.
Step 20: Play Bus Jam. Sometimes you get on the bus and sometimes you don’t. Bus Jam is so much like life, man.
Step 21: Search for ways to start selling your “under-wares” (why the fuck is no one hiring me with gold like that?) and run into a bunch of people on Reddit saying something to the effect of “it’s not that easy, honey.”
Step 22: Change a few words in one of your template cover letters and send it off. You get an email instantly saying they are no longer accepting applications.
It’s been a minute so there’s a lot!
podcasts.
MY PODCAST: SORRY FOR YOUR LOSS!!
I launched a podcast with my friend Jamie about grief called Sorry For Your Loss. We have two episodes out right now, including what not to say to people grieving. I’d love if you listened and reviewed!
The Endless Honeymoon Podcast- “Citizen is a Verb” with Baratunde Thurston
This is such a soothing listen for feeling helpless in ~these times. Comedian and activist Baratunde Thurston blends action items with humor and talks about how even the smallest actions can start to create waves in your community. Also, funny relationship advice from Moshe Kasher as always.
Death, Sex & Money - A Middle-Aged Couple Made Porn to Spice Things Up. Then One of Them Got Fired.
This was so fascinating. I also loved how the guy who did porn with his wife and got fired is now suing his university for firing him and taking away his tenure because is it really a crime if your professor does porn on his own time?!
Glamorous Trash - Sarah Wynn Williams’ Memoir Careless People (with Traci Thomas and Becca Platsky)
Love Chelsea Devantez’s breakdowns—and sometimes takedowns—of celebrity memoirs. Sarah Wynn Williams worked at Facebook in the early days and gives some insight (without realizing how guilty she is herself) into how it became the monster that it is. There’s a lot of great discussion on this ep about how insecure Mark Zuckerberg and Elon Musk are as well. Chilling to hear “People are dying because these insecure men want friends.”
books.
Say Everything - Ione Skye
I cannot shut up about this book. I’ve always admired Ione Skye as a cool girl who dated cool people, but she was always someone we heard more about than from. In this book, you get such an honest, artfully written take of girlhood, exploitation and womanhood all set against 80s and 90s Hollywood. Skye holds nothing back and calls out people for wronging her just as often as she admits her own faults. I also met her at a book signing and she was very nice to me. And, gotta again plug Glamorous Trash for the ep on this book!
movies.
Mickey 17
I would recommend this solely for Robert Pattinson’s doofy little voice he puts on. Also, a sweet and optimistic political commentary.
music.
Come Onn - Ethan Tasch
I’ve been really into Ethan Tasch recently. Just a fun indie folk vibe.
Slugger - Sasami
More songs need to name drop what astrological sign they are.
Honey Toast - The Greeting Committee
Dream pop that is so soothing.
tv.
The Studio
Seth Rogen is such a pro at creating scenes that get my heart racing with anxiety. Such a funny and often “too real” look at present day Hollywood’s fight between art and business.
One more thing!
LA! I’ll be performing a story as part of a fire relief benefit So Say We All is putting on. Come see me!
Relatable haha