Dear Prudence is Slate’s advice column. Submit questions here.

Dear Prudence,

I live about four hours away from my daughter and grandson, so I see them somewhat regularly, but not day to day. I am starting to get very worried about the way my daughter babies him. He is nearly 9, and can’t cut his own meat, pour his own drinks, or pick up his own clothes. My daughter treats him like a toddler and scolds me for encouraging him to be a little more independent. If he doesn’t want the food he chooses at a restaurant, I will not re-order for him. I will tell him that this is his food and if he doesn’t like it, we will go home and he can make himself a sandwich. My grandson says he doesn’t “know” how to make himself a sandwich. We’ve been through this song and dance enough that I know he can make one. He knows if he drags his heels enough, mom will give in and do everything for him.

My grandson isn’t autistic or developmentally delayed. His parents divorced two years ago, and he seems to have regressed. And my daughter seems to be encouraging it. She recently told me how her latest relationship fizzled out because her boyfriend was uncomfortable sleeping with my grandson.

He didn’t have nightmares and wasn’t sick, but my daughter thought it was “fine and normal” that her son co-sleep with her and her partner and that he was “too weird” about it. I asked if they had been intimate. She told me that wasn’t a problem. I love them both, but I really think my daughter is harming her son.

I watched him for a weekend recently while my daughter worked, and he ended up throwing a screaming fit because he “forgot” how to put his shoes and dishes away after multiple reminders, and I told him that he lost iPad privileges. My daughter’s response was immediately to give him his iPad back, and she told me I didn’t have the authority to take it away. I am not force-feeding him poison; I am asserting bread and butter consequences here. My daughter isn’t getting the message no matter how I phrase things. I am ready to just withdraw for my own sanity. Help!

—Helpless in the Heartland

Dear Helpless,

I would hate for you to withdraw and give up relationships with two people who you love. So let’s talk about other options for maintaining your sanity.

Could you think about stepping back, not from the relationships, but from the idea that the way your grandson is raised is your responsibility? Could you envision a world in which you trust that your daughter is doing her best —or pretend as if you trust her because you respect her? Please try. You’ve had your chance to parent a child. I’m sure you did your very best. But for what it’s worth, you raised someone who you think makes bad choices and who doesn’t listen to you. One could argue that your relationship with her demonstrates the limits of using your power over a child to try to shape their behavior. What happens when they’re old enough to decide on their own screen time, order their own food, and … decide on their own parenting style? You’re living that now. You can no longer enforce what you want her to do by putting your foot down, being firm, and deciding what she can and can’t have. And since that sounds like it was the primary tool in your parenting arsenal, you’re left feeling helpless and extremely frustrated.

Are you at all open to the idea that your daughter has a different approach, and that might not be the wrong approach? Or maybe it’s a less-than-ideal approach, but the only one she is capable of using right now?

It’s possible your grandson has a diagnosis that explains some of his challenges, and your daughter isn’t comfortable sharing it with you, because you two don’t have a history of being vulnerable with each other and connecting as equals. I know for sure you won’t get more information or be asked for input until you change that.

And even if you’re right that your daughter’s permissive parenting style is directly responsible for stifling your grandson’s development—even if it’s true that if she would simply be stricter, he would know how to get dressed and make a sandwich—do you really think you’re going to undo all that by laying down the law when you occasionally see him? I don’t.

Give yourself a new job description as a grandmother—one focused on enjoying your grandson and forming a deep connection with him. If your worst fears are true, and he’s going to struggle his whole life because his mom won’t be strict, he’s going to need you in his corner. And you might get something out of an experience you haven’t had before: loving a child without constantly strategizing about how to shape their behaviors.

Dear Prudence,

The woman I have been in love with for years, “Christine,” is getting married in June. Her fiancé is a miserable, self-centered asshole, but she either can’t or refuses to see it. She has always seen me as a friend and confidante; I have been too shy to reveal my true feelings to her all this time until now. Should I say something to Christine before it’s too late?

—Tortured

Dear Tortured,

While making a huge announcement right before Christine’s wedding would be a good plot point in a romantic comedy, no, I don’t think you should say anything. If you were in love with her for all these years, and she had any romantic interest in you at all, you two already would have had some sort of moment. I’m sure of it. It’s very unlikely that she’s also been in love with you and too shy to say anything. I believe that she’s making a bad choice and that you’re a better person than her fiancé, but people’s relationship choices are often not based on a clear-eyed assessment of who would treat them the best.

My Uncle the Priest Is Coming to Visit for Father’s Day, and My Mom Has Made an Unholy Request My Brother Divvied Up Our Dad’s Estate. But I Just Found Something Very Off. This Content is Available for Slate Plus members only I’ve Complained About My Messy Sister to My Daughter for Years. But I Didn’t Think She’d Take Matters Into Her Own Hands! My Husband’s Most Recent Way of “Teaching Our Son Responsibility” Involved a Sledgehammer. I’m Speechless.

For whatever reason, Christine is drawn to this terrible guy. She may stay with him forever, or this may be an experience she needs to have to clarify that she’d rather be with someone who is not miserable and self-centered and is a true friend to her. But even if that’s the case, you can’t rush the process. Don’t put the pressure of saying something before it’s “too late” on yourself—you really don’t have the power to change her feelings.

If you think you’re able to continue to be a good friend to her (being appropriately platonic, not behaving weirdly because of jealousy, not going out of your way to pick fights with her husband), and if you really value her as friend who may never turn into more, keep doing what you’ve been doing. But if you know in your heart that you’ll never be able to accept her being with someone else, take a step back from the relationship. You have my permission to stay in touch enough that you’ll know if she gets divorced and decides she doesn’t like assholes anymore.

Dear Prudence,

How many drinks is it permissible to have at a party without appearing to be a lush?

—Cocktail Connoisseur

Dear Connoisseur,

I sincerely believe that if you’re asking this question, you’re already a lush and are not going to limit yourself to any number I say. Ask yourself instead (and maybe poll those around you) how many drinks have you historically been able to have before you make a scene, become unpleasant to be around, or feel horrible the next day—because your concern about how you are perceived tells me that these things are probably a regular occurrence. Whatever that number is, stop one drink earlier at the next party.

Catch up on this week’s Prudie.

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