It seemed like I should enjoy this book. How could philosophy be anything but interesting, especially philosophy presented for the modern world?

But I just couldn't get into it due to two flaws:
(1) Second-person point of view.
Each chapter of the book begins with a fictional anecdote of a person facing some difficult aspect of life, such as exclusion, romantic rejection, death, obsession, disappointment, illness, or other struggles. The protagonist of each anecdote grapples with a breaking-up boyfriend, a compulsion to shop, an inability to enjoy the present moment while on holiday, and so on. The author uses each anecdote to springboard into a particular philosopher's advice.

Seems harmless enough, right? But the author made one mistake: she wrote these anecdotes in second-person view. She doesn't talk about how "Tom was bitterly disappointed by his foolish error", but instead says "YOU were bitterly disappointed by YOUR foolish error."
This has an annoying effect where the author seems to be relating a series of obviously false facts. Things like: "Worried about how your work colleagues would perceive you, you dressed up to the nines and wore your finest pencil dress." It's so absurd that it kept breaking my absorption of reading the book.
All of this would be fixed if the anecdotes were instead about some third-person characters. Make up a "Sarah", "Amir", or "Liselle" and talk about them, not about me.

(2) Too specific, then too vague.
Compounding the problem above was the fact that the fictional scenarios were very specific. Using the second-person "you" would have been fine if the statements were vague enough to apply to the majority of readers, e.g. "No matter who you are, you're likely to encounter death at some point in your life."
But instead the author gives extremely specific fictional anecdotes about how "you" went shopping at IKEA, how "you" gussied yourself up to see your boyfriend, how "you" had an adorable dog for years and years.

Then after these overly specific anecdotes, the advice that follows is very vague. We get a few generic comments about how the anecdote could have gone differently ("Do go to the party, but don't drink so much!" - gee, thanks, I would never have guessed) followed by vague platitudes that have no clear relevance to any other scenario ("Don't get overly passionate", "happiness is the meaning of life", etc).

Overall, I don't recommend reading this book.