What’s the biggest mistake you’ve watched someone make in their personal life?

Oh, plenty, but the one that makes me saddest is an old friend of mine from college. She's brilliant, has written many books, and lives in a cute little condo in an artsy-beachy community. In many ways, her life looks awesome from the outside.

She always longed to get married and have children, but for whatever messed up reason absolutely refused to date or consider dating the kind of guy that could actually make her happy. She always, always went for the soulful, tortured, loner artist with issues. Which is one thing when you're 25 and super cute. But a whole different proposition when you're 50. She got down to the bottom of the barrel, and then she got in the barrel and started digging.

Her self-esteem is non-existent now. The last time she told me about her latest on-again, off-again boyfriend, my jaw dropped because this brilliant badass feminist was being emotionally abused by some trashfire who berated and threatened her when she wouldn't give him money for his pregnant "real" girlfriend.

And she went back to him. Over and over.

All of her books now are about missed opportunities, regret, and death. And they're not literary fiction, they're supposed to be commercial, like chick-lit. But she can't sell them, because nobody buys chick-lit about death.

She's been to therapy. She does all kinds of self-care and empowerment retreats and meditation, and I don't know what all. But she has this enormous blind spot about her actual choices and the way they are impacting her life.

It breaks my heart.

/r/AskReddit Thread