In her new book, Tess Smith-Roberts turns disaster dating stories into hilarious comic strips

“It’s by far the most well-received project on my Instagram,” says the illustrator. “I guess we all just love bad date stories.”

25 October 2023


“It all started in September 2020 after I’d been on a string of terrible dates and I was getting a bit fed up with it,” says Tess Smith-Roberts on the origins of her latest book, Disaster Dates & Lucky Escapes. “Then one day, one of my friends mentioned that I should make a book about my dating stories.” Initially afraid to share details of her love life with the world, Tess began by asking her followers on Instagram for their funny anecdotes. After receiving an amazing response, she was inspired to turn them into a series of short comic strips – and even to include some of her own personal experiences in the collection.

These illustrations became her most sought-after pieces of work. Funny, quirky and relatable, they reassured Tess’ followers – and Tess herself – that they weren’t the only ones having bad luck on the dating scene. “It kind of felt like therapy to me, getting all of these bad date stories and then drawing them,” she recalls. “I was like ‘Oh, I’m not the only one. Other people have been on shitty dates, and a lot of them are a lot worse than mine!’”. Tess made these comic strip stories a regular feature of her output, and over the course of the next two years, they grew in popularity. Until, in spring of 2022, the team at Kyle Books got in touch with her asking for them to be turned into a full-blown publication.


Tess Smith-Roberts: Disaster Dates & Lucky Escapes (Copyright © Tess Smith-Roberts, 2023)

“It was such a leap going from four or five silly comic panels to a whole entire book,” says Tess, who spent the next six months producing it as she travelled around the world. Working in cafes in the US, Central America, South America, and Asia, she drew around 90 pages of bad dates that were partly hers, partly her followers, and partly imagined. Though they were stories belonging to many different people, in the book most of these dates are experienced by the protagonist Olive. We follow this character as she navigates her tricky love life, and ends up in the dating version of AA. “The leader of the group is actually a witch,” explains Tess. “So some more stupid stuff happens, like a curse and a love potion – all while she is going on more bad dates.”

Asked about her favourite stories from the new book, Tess admits the one about Olive going on a date with “Orange Juice guy” holds a particular fascination for her: “The person who sent it to me must have made it up a bit… Why would someone steal that much juice? It’s just so silly.” Another one about Olive going on a date with a guy who “orders every single item on the menu and only takes a bite out of each one” is another contender, she says. “And then he asks to split the bill – unhinged behaviour!”

Disaster Dates and Lucky Escapes by Tess Smith-Roberts is out 26 October 2023, published by Kyle Books.

GalleryTess Smith-Roberts: Disaster Dates & Lucky Escapes (Copyright © Tess Smith-Roberts, 2023)

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Tess Smith-Roberts: Disaster Dates & Lucky Escapes (Copyright © Tess Smith-Roberts, 2023)

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About the Author

Daniel Milroy Maher

Daniel joined It’s Nice That as an editorial assistant in February 2019 and continues to work with us on a freelance basis. He graduated from Kingston University with a degree in Journalism in 2015. He is also co-founder and editor of SWIM, an annual art and photography publication.

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