Dear Prudence

Dear Prudence Uncensored: “Bailing on Bali”

This week, Jenée Desmond-Harris and Lili Loofbourow discuss a Prudie letter: “Bailing on Bali

Jenée Desmond-Harris: I say this all the time, but I literally can’t believe how many family members feel entitled to each other’s money. It is SHOCKING. She even said she wanted an “advance” on “her” money! Wtf.

Lili Loofbourow: I KNOW!!! Poor Bailing on Bali! I thought the second-to-last line of this was the saddest, about not wanting to damage the relationship with their father.


Jenée: Me too, especially because it just doesn’t seem like the relationship is super robust or healthy to start with.

Lili: It clearly isn’t, right? And this poor person has helped his/her step-siblings and now risks getting punished for that by the parent who appears to have done the least for them? WTF!


Molly is bad news. Even at 18, when so many of us are assholes, that kind of triangulation is really ugly.

Jenée: Yeah, she’s a monster.

Lili: I was looking up how you’re supposed to deal with that kind of thing—triangulation, I mean—when other parties get pulled into a conflict.

Jenée: Ooh, any insight? Beyond my “screw them” approach?


Lili: I think your “screw them” approach is pretty much right on, sadly. “Ignore attempts to bait or manipulate you” is one piece of advice. “Refuse to let yourself be drawn in to competitions, attempts to praise or elevate you, or private confidences.” “Avoid sharing any personal details with them.”

Jenée: YES—I so agree with not sharing personal details. And not overly justifying.

Lili: How much of a relationship can you really have with someone when this is what you have to do just to remain intact? Your “budget” script was perfect, and doubles for the “I will not be paying for this entitled young person’s education either.” But I am still so sad for LW, who does not seem that concerned about their relationship with Molly, but who clearly has tender feelings about their recent relationship with the dad!


Jenée: I’m sad for them too, especially because I get the feeling they have so much money that they actually could afford this without it being a huge deal.

Lili: Ooh. That’s a good point.

Jenée: And they might be tempted to write the check / make the cashapp transaction just to keep their dad happy.

Lili: Oh mannn.

Jenée: Which, even if it wouldn’t be financially devastating, would just be sad. Because I don’t think they’re going to get the love they want in return. The father’s wife isn’t going to start calling to check in.


Lili: Right.

Jenée: Molly isn’t going to start being a delight. Dad isn’t suddenly going to care more than he has before.


Lili: No, although I suppose there’s a chance she could outgrow her assholehood. Though odds of that are going down given what we know re: how she’s been parented.

Jenée: Yes, she totally could. I should be more generous to her. But they’re still not going to have a close relationship. I feel like that ship has sailed.

Lili: I think the not-so-secret story here, which breaks my heart, is that you can see a child (even if they’re an adult) dealing with the fact that their parent parents someone else, someone younger, very differently. It’s an ugly contrast, and because of how this has escalated, it’s making preferences painfully known.


Jenée: Yes, I get letters like this all the time. Making a sweeping generalization here: Dads are huge on just starting over with a new family like the old one never happened and treating the new kids much better.

Lili: Yes. And this is an especially cruel kind of weird parenting—it’s making the child who was not parented responsible for parenting the child that was! It’s just … untenable!! I’m so mad for LW.

Jenée: I hope they take some of the extra money they have and do something really nice for themselves (therapy if they aren’t in it already! a massage! a nice experience with friends or family who consistently value them for who they are, not what they have!)

Lili: I hope so too. Maybe with those step-siblings—who aren’t “actually” family, per our young brat—but who seem to like LW, and value them in a less literal way. LW: YOU DESERVE BETTER!