Dear Prudence

Dear Prudence Uncensored: The Sisters and the Boyfriend

Every week, Danny Ortberg and Nicole Cliffe discuss a Prudie letter. This week: the sisters and the boyfriend.

Nicole: Ugh, Andrew sucks HARD.

This is so crummy. And obviously everyone involved is an adult so your ability to intervene meaningfully is basically nil.

It sounds like you have already tried to talk to her about the pain this will cause Lilah, and it’s impossible to explain to a 20 y/o that they are getting played by an older guy and this will end badly.

Lisa HAS asked for help telling Lilah, which gives you an opening of some sort.

A FOUR YEAR RELATIONSHIP which ended badly, this is such a disaster.

Danny: didn’t this show up semi-recently in one of your r/relationship threads?

Nicole: I would probably want to tell Lilah myself, before Lisa talks to her.

Danny: from the point of view of the sister?

Nicole: Yes, a similar thing

Danny: it must be so hard as a parent when your only-very-recently-minted adult children do dumb and thoughtless things to hurt one another!

Nicole: Because I would want to be candid and supportive and ask what *she* needs through this.

Danny: because I agree that the most the LW can do here is really encourage Lisa to tell Lilah right away and to prepare her that it’s going to hurt Lilah quite badly, when only a few years ago you could have, I don’t know, sent them both to their rooms until they apologized and instituted a no-boyfriends policy (which might not have been super effective in terms of maintaining sisterly harmony but would have at least let you feel like there was something you could do)

but as it is, you’ll probably have to watch your daughters not like each other for a long time

Nicole: Yes


This will not be something you can stop, and it will be bad.

Danny: and yes, definitely try to balance between not letting Lisa get totally isolated by this creepy older guy

Nicole: And this guy is bad.

Danny: while also really supporting Lilah because this is going to hurt so much

Nicole: RIGHT, oh, so true

Danny: this guy is absolutely doing this on purpose

Nicole: You do not want it to become “us against the world”

You want to remain actively in Lisa’s circle of love and support

Danny: and it is impossible to convince a 20-year-old that they are not making a totally rational decision or that their older partner isn’t in fact an amazing person

maybe when she’s 29 she’ll look around at 20-year-olds and think, “Oh, wow, that’s EXTREMELY not cool, what he did”

Nicole: Yes.

Danny: but mostly you will have to let your daughters fight this one out

Nicole: I think so. Which is a frustrating answer to get, but the truth

Danny: and I also think it’s OK to say to Lisa, “Remember how devastated your sister was when he ended this relationship less than a year ago, and don’t ask her to be happy about this. That would be cruel.”

obviously you don’t want to come down too hard on her but I do think it’s OK to gently remind her of, you know, reality

Nicole: Yes, you can. It’s good for her to hear that this behavior is unkind, and that she needs to be prepared for the news to be received with anger/sorrow/confusion.

Danny: and that saying that is not the same thing as saying “You’re a bad sister and I condemn you”

Nicole: Yes!

Danny: also I hope Andrew’s next dental appointment goes very badly and he has to have a lot of very expensive bridgework put in

do people still get bridgework?

Nicole: I think so??? At LEAST he needs a complicated root canal