Suggest me a book about the grief of having a non-existent dating life

Trying to get out of a reading slump, and I've decided to read something that helps me deal with what I'm feeling instead of escaping it. Dealing with the grief of 'falling behind' in every aspect of life – dealing with unsupportive parents, not being able to make much of my career, and dealing with a dating life where I have zero experiences, no matter how hard I try. Would love book suggestions that maybe make me feel less alone and help me deal – either through giving me a sense of catharsis or by giving me hope. Open to all genres. Thanks!