Books to Make Someone Laugh Through a Hard Stretch
For a friend, sibling, parent, or partner in the middle of a stretch where things are not fine — and who could use something sharper than sympathy or borrowed hope. These books don’t try to fix the grief, the illness, or the bad luck; they just sit in the mess and find a joke that lands anyway. Chosen for wit that survives the worst days and for authors who write straight through their own punchlines, these are books that can make room for a laugh in spite of everything, not instead of it. They are written for adults: the humor is dark and frank, and they deal with death, suicide, depression and illness. Send one only if you know a laugh would be welcome right now, and start with the one whose humor sounds most like theirs. You don’t have to send them all.
TMM Editorial · May 2026
The Picks
No Happy Endings by Nora McInerny
McInerny lost her second pregnancy, her father and then her husband within a few weeks — and later started a podcast about it. The book to send to the friend who is in the worst stretch and still texting jokes.
Furiously Happy by Jenny Lawson
Lawson on living with severe depression and anxiety, and on grabbing the good days hard when they come (2015). Funny and frank, and never a cure. For the recipient who is tired of being told to think positive.
Let's Pretend This Never Happened by Jenny Lawson
The Lawson entry point (2012) — childhood in rural Texas and a taxidermist father with a habit of dead-animal hand puppets. For the friend who could use something absurd to read on a bad night.
Calypso by David Sedaris
Sedaris near sixty (2018), writing about his sister's suicide, his father's old age and his own mortality, with the jokes intact. For the literary recipient navigating their own middle-aged stretch.
Broken (in the best possible way) by Jenny Lawson
Lawson (2021) on depression, an experimental treatment for it, and an open letter to her insurance company. For the friend with a long-running diagnosis who is tired of inspirational quotes.
Wow, No Thank You by Samantha Irby
Irby's Lambda Literary Award winner (2020) on turning forty, newly married and living in Michigan — every neurosis catalogued without apology. The strongest Irby entry point if your friend has not read her yet.
Quietly Hostile by Samantha Irby
Irby in 2023 — working with the women of Sex and the City, her teeth, her QVC habit, and the less glamorous bits behind them. For the recipient already on board and waiting for the next one.
We Are Never Meeting in Real Life by Samantha Irby
The 2017 collection that brought Irby a wide audience — the Bachelorette application essay alone earns the shelf. For the deep-cut reader who wants the whole catalog in chronological order.