looking for a unicorn

I am looking for a book for an early 20s man going through it. He's in a phase where he's trying to figure out what he wants/who he is. He has an unsupportive family and isn't a huge reader. Ideally this book would be:

• a collection of short stories (or otherwise bite-sized and easily digestible pieces)
• light-hearted and a bit funny

Bonus points if topics in the book include:

• Healthy and non-toxic masculinity
• Self-esteem

Bonus bonus points if I can get it as an audiobook