Too Good to Leave, Too Bad to Stay
by Mira Kirshenbaum
Why read this book
- Replaces the useless "list the pros and cons" advice with actual diagnostic questions.
- Each question is backed by what other people in the same situation were later glad they did.
- It's for the specific, miserable state of ambivalence — not knowing — which most relationship books ignore.
- Short, practical, and oddly calming if you're stuck.
In one sentence
A decision guide for anyone stuck on whether to stay in or leave a relationship, built around 36 diagnostic questions instead of the usual pro/con list.
Key takeaways
- The pro/con balance sheet doesn't work for relationships, because feelings aren't weighted equally and the list never resolves. Kirshenbaum uses diagnostic questions instead.
- The framing flips the usual question. Instead of "is it good enough to stay?", you ask whether it's "too bad to stay in" — your relationship is good enough unless a specific guideline says otherwise.
- The sharpest question is the last one (#36): "If all the problems in your relationship were magically solved today, would you still feel ambivalent?" Lingering ambivalence after that thought experiment is itself the signal.
- Sadness about leaving doesn't mean leaving is wrong: "feeling sad at the thought of leaving doesn't change things."
- "Too good to leave" couples usually share a sense of fit or a joint project bigger than the relationship itself.
Summary
Most advice for a stay-or-leave decision is some version of "make a list of pros and cons." Kirshenbaum, a couples therapist, argues that's exactly why people stay stuck for years: a relationship isn't a balance sheet, and the list never tips.
Her alternative is a sequence of 36 diagnostic questions. Each one is a specific yes/no — about respect, fun, intimacy, shared goals, whether you'd still be ambivalent if the problems vanished. And each is tied to an empirical guideline: among the people she worked with who answered a given way, most were later either glad they stayed or glad they left. So instead of weighing feelings, you're matching your situation to outcomes other people in the same spot actually had.
The book reframes the core question. You're not asking "is this good enough to justify staying?" You're asking whether it's "too bad to stay in" — and the default is that it's worth staying unless a clear guideline says it isn't.
Reflections
The useful takeaway for me is narrow: a pro/con list is the wrong tool for an emotional decision, and a set of diagnostic questions is a better one. The question I'd actually keep is the last one. If every problem vanished tomorrow, would you still feel unsure? That cuts through the noise faster than any list.
“"Your relationship is too good to leave if no guideline points to the fact that it's too bad to stay in."”
— Mira Kirshenbaum
Who should read this
- Anyone genuinely stuck in ambivalence about a long-term relationship.
- People who've tried the pro/con list and ended up more confused.
- Skip if you've already decided — this is a tool for deciding, not for justifying a decision you've made.
Favorite quotes
- "Your relationship is too good to leave if no guideline points to the fact that it's too bad to stay in."
- "If all the problems in your relationship were magically solved today, would you still feel ambivalent about whether to stay or leave?"
- "The most important thing for you to know is that your sadness doesn't mean that the truth you've found isn't your truth."
- "There's a special way you're weird and a special way your partner's weird and there's something about your joint weirdness that fits perfectly."
- "Does your relationship support your having fun together?"
FAQ
What is Too Good to Leave, Too Bad to Stay about?
Deciding whether to stay in or leave a relationship using 36 diagnostic questions rather than a pro/con list.
What is the most important question in the book?
#36: if every problem were magically solved, would you still feel ambivalent? Lingering ambivalence is the signal.
How do the 36 questions work?
Each is a yes/no tied to a guideline based on whether people who answered that way were later glad they stayed or glad they left.
Is it worth reading?
Yes, especially if you're stuck in ambivalence — it's practical and short.
Chapter-by-Chapter Breakdown
Click to expand the full detailed notes for every chapter →
Chapter-by-Chapter Breakdown
Click to expand the full detailed notes for every chapter →
Grouped from the highlights. The method: 36 diagnostic yes/no questions, each tied to whether people who answered that way were later glad they stayed or glad they left. Themes covered: respect and contempt, whether you still have fun together, intimacy, shared goals or a sense of "fit," and the final ambivalence test (#36). The reframe throughout: ask whether it's "too bad to stay," not whether it's "good enough to stay."
