Families who loved Dates, Double Dates and Big, Big Trouble by Karen McCombie often look for books with a similar feel. These 20 recommendations were selected for their similarity in style, theme, and reading level.

A parent should reach for this book when their middle schooler is starting to navigate the confusing, anxiety-inducing world of first crushes and shifting friendships. It's perfect for a child who feels overwhelmed by social expectations or is worried about saying the wrong thing around someone they like. The story follows Ally, whose secret crush on a boy gets wildly complicated by a misunderstanding with her best friend, leading to a disastrous plan for a double date. The book humorously and gently explores themes of self-confidence, friendship, loyalty, and the normal awkwardness of growing up. It’s an excellent choice for reassuring young readers that their feelings are valid and that communication is key, all wrapped in a funny, lighthearted package.