Josh Sundquist is a cancer survivor, Paralympic ski racer, motivational speaker, and stand-up comedian. Sundquist’s memoir Just Don't Fall: How I Grew Up, Conquered Illness, and Made It Down the Mountain was published in 2010 and became a national bestseller. While his first memoir showed how he was able to overcome health challenges to become a sporting hero, his second book We Should Hang Out Sometime: Embarrassingly, a True Story (2014) deals with the most difficult mission in his young life: to find a girlfriend. In an October 13, 2014 review, Publishers Weekly describes Sundquist’s investigation into his unsuccessful love life as “equal parts hilarious and cringe-inducing.” This comment references the text’s balance of humor with detailed accounts of emotionally painful experiences.

We Should Hang Out Sometime premiered as a one-man comedy show at the Santa Monica Playhouse in 2019. Sundquist further explores how disability influences a person’s love life in his novel Love and First Sight (2017), which shows how a boy who is blind, Will, navigates a romantic relationship before and after his cornea transplant.

Summary

When Paralympian and motivational speaker Josh Sundquist reaches the age of 25 without ever having had a girlfriend, he launches an investigation into his failure. He determines that he will revisit the scenes of his near-misses with women and then interview them to find out why they rejected him. Sundquist wishes to know whether the women’s reasons for rejecting him are based on factors he can change, or are rooted in permanent characteristics, such as his being an amputee.

Sundquist’s first crush happens when he is 13, four years after his leg amputation due to cancer. The girl is Sarah Stevens, from his church youth group. Sundquist, who is insecure because of his differences from the other kids, is nervous about asking Sarah to be his girlfriend. He finally summons the courage, and Sarah agrees to be his girlfriend. To Sundquist’s horror, she breaks up with him a day later over Instant Messenger. Years later, at the time of his investigation, Sundquist is still unclear about what happened. When they meet, Sarah tells him that she had never had a boyfriend before and was so nervous that she started crying when Sundquist asked her out.

When Sundquist convinces his conservative Christian parents to trade home school for public high school, he sets his sights on Liza Taylor Smith. He soon learns that Liza is the most sought-after girl in school, and is delighted when she invites him to her church youth group. However, when Sundquist cannot participate in the pumpkin race owing to his disability, he is so self-conscious that he gives up on Liza. At the time of the investigation, when he bumps into Liza in the mall, he gets the impression that she never had romantic feelings towards him.

Sundquist next becomes interested in Francesca Marcelo, a girl who is attractive, but does not strive to be popular in the conventional way. He is surprised that she agrees to go out with him, and that she isn’t put off by his prosthetic foot turning the wrong way during a golfing date. While he wants to kiss Francesca, he is so nervous that he finds an excuse not to. By the end of the summer, he still hasn’t kissed her. Years later, when he asks Francesca why a relationship never blossomed between them, she throws the question back to him, indicating that he should be looking for the answer inside of himself.

Sundquist’s next love interest, Evelyn Williamson, a girl at his church group, flirts with him while being in an on-off relationship with a long-distance boyfriend. She agrees to go to prom with Sundquist, where he has been nominated for Prom King. He feels disappointed when he does not win, but hopes to strike a romantic tone with Evelyn on the dance floor. She is however cold to him and they eventually go their separate ways. At the time of the investigation, a married Evelyn confesses that she had a crush on Sundquist, and that she wished he had asked her out during the “off” periods with her long-term boyfriend.

At college, Sundquist makes a group of friends who tell him that the reason he has never had a girlfriend is because he has never defined the relationship with any of the girls he likes. Sundquist attempts to do this with Lilly Moore, an attractive girl who he has little in common with. When Lilly rejects his advances, he nevertheless cannot give her up and calls her every day of the summer. While he continues to pine for Lilly all four years of college, he has his first kiss with his friend Katie, and acquires an admirer in the form of Stella the stalker, a girl whose behavior reminds him uncomfortably of his own. At the end of college, Lilly seems to be curious when Sundquist’s drunken friend accidentally reveals his continuing crush. However, at the time of the investigation, Lilly cannot even remember this incident and Sundquist concludes that she is indifferent to him.

As Sundquist’s career as a motivational speaker grows, so does his confidence. He approaches and asks out a Miss America contestant called Sasha Wright. The two enjoy a warm, long-distance correspondence and even meet up in person a few times. He decides that he needs a grand gesture to declare his feelings, and so finds a way to attend the Miss America contest. Sasha, who is in a bad mood after a disqualification in the first round, is cold to him and does not return his calls. He decides to stop calling her. When he meets Sasha again, at the time of the investigation, she is engaged to a man she met three months earlier. However, she tells him that at one stage, she wished he could have been her boyfriend and hints that he gave up too easily.

Sundquist declares his investigation inconclusive. However, when he watches a movie about a kid who loses a limb, he gets insight into why he gave up at the first obstacle in his romantic endeavors: He considers himself inferior because of his amputation, and therefore unworthy of a relationship.

Later, a more self-accepting Sundquist meets Ashley Samsonite and begins to date her. She likes him, but is wary of being his girlfriend straight away because he has never had one before. While he is disappointed, he remembers his lesson from his previous romantic trials and continues to pursue Ashley. She agrees to be his girlfriend, and in time, his fiancée. Sundquist realizes that there was never anything wrong with him, and that being an amputee makes him no less worthy of love or a relationship.