Our advice columnists have heard it all over the years—so we’re diving into the Dear Prudence archives to share classic letters with our readers. Submit your own questions to Prudie here.

Dear Prudence,

 I am the 28-year-old only child of a very loving, very overprotective mother. She kept me close to home as a child; now I’m living two hours away and going to grad school, and she is obsessed with keeping me “safe.” She insists that I call or text her to check in every night after I get home, usually around 9, to make sure I got home safe. If I tell her I’ll be calling later than that, she wants to know why, which is a problem if I’m going somewhere, like a bar, that I know she won’t approve of. If I tell her I’m going out somewhere, she will go online and work out which bus route I’m taking so that she can keep track of where I will be and when. A few weeks ago, I let slip that I went to the movies with a girl I met on Tinder (I’m a lesbian) and she freaked out: “You met someone on the internet? Did you tell anyone else where you were going? Would anyone have noticed if you didn’t come home? Why didn’t you tell me?”

I love my mother, but I feel like this constant surveillance is preventing me from living an independent adult life. I’ve tried to talk to her about it, but she always comes back with “I’m just trying to keep you safe!” and starts citing statistics about how many murder victims meet their end because no one knew where they were going. (Before you ask, she does not listen to true crime podcasts; I have no idea where she’s getting this.) How do I manage my mother’s anxieties while disentangling myself from her apron strings? (My dad, for the record, is much more laissez-faire: He’s content if we talk on the phone once a week.)

—I’m Safe!

Dear Safe,

Your mother needs to go on an information diet, today. You do not have to defend yourself or get sucked into these carousel-like disagreements if you do not want to. This is not your fault, she’s obviously been preparing you from childhood to be instantly accountable for your whereabouts and doings, but you absolutely do have the power to end it.

Your job is not to “manage [your] mother’s anxieties” as you begin disentangling yourself from this situation. She is an adult. If she were not your mother, it would be easier to see this bus route nonsense as stalking behavior. The first step is going to be telling her, in advance, that grad school is extremely demanding and you’re too busy to do these nightly check-ins. Suggest one night a week to call and “catch up.” If she spends that time flipping out about your very reasonable boundaries, you can say you’re not interested in talking about that, make one attempt to change the topic, and then say, “Well, I should get going, love you!” and hang up. Your job is to be consistent. That’s all you have to do.

Things that could happen:

1. She could call the cops when you do not call her or answer her calls.

2. She could show up on your doorstep.

3. She could send you a person-size box and pop out of it.

4. She could send you a guilt-size box filled with all your childhood possessions and a note about how, since you don’t care about her feelings, it seems silly to hang onto them.

Consistency. Each time: “That doesn’t work for me.”

Keep me posted. I know you can do this.

—Nicole Cliffe

From: Help! I Work With a My Little Pony Superfan Who Wants to Be Called “Starfire.”. (December 2nd, 2019).

Dear Prudence,

I am a freelance Web developer who was almost bankrupted by the economic collapse. A few years ago a client referred me to a friend who needed some search engine optimization. The friend operates an adult website. Adult websites make a lot of money but have trouble finding honest, competent help. One job turned into another, and working with adult websites has become a thriving business for me. My problem is that nobody knows I do this. My wife thinks that I design websites for local companies. I don’t work with sites that do anything illegal or that produce “desperation porn.” My clients are high-end, soft-core sites. I’m getting to a point where I can’t hide this anymore. I’m going to get a prestigious industry award, which means that an Internet search of my name will reveal the nature of my business. I also have had to hide profits in a secret mutual fund, because I don’t think my wife would believe that I make that much from designing websites for florists. I’ve wanted to walk away for a while, but the money has gotten us a lifestyle that we struggled to have for years. My wife doesn’t have to work anymore, our house is paid off, we have a college fund for the kids. I feel like I’m stuck between disappointing my family by turning off the money pump or having them find out that I work in the adult entertainment industry. I need advice.

—Not Quite Walter White

Dear Not Quite,

I did not watch Breaking Bad, so I don’t know if Walter White had your dilemma of receiving an award from the crystal meth manufacturers of America. Your immediate problem is easy to solve. You thank the heads of your industry for their generous recognition, then you inform them that for personal reasons you must decline the award and ask that your name be deleted from the event. Alternatively, you could say to your wife, “Hon, I’m being honored at a big industry award ceremony and I want you to come!” The evening would be revelatory for her, and you two would have plenty to talk about during the car ride home.

This was the first I heard of “desperation porn,” the plot of which revolves around the (usually female, often clothed) star’s ultimately unsuccessful struggle to find a place to pee. I don’t understand your scruples about this harmless-sounding genre, and if others want to make beautiful urination movies, let them get showered with money. As for what you do for a living, I don’t see that it’s wrong or something to be ashamed of. You’re helping provide a service for which millions are grateful. The only true red flag in your letter is your hiding your profits from your wife. If you file a joint tax return and you aren’t declaring all your income, that sounds more compromising than your work. Maybe your wife is like Carmella Soprano—she knows but doesn’t want to know. Surely she realizes that the economy has not rebounded so dramatically that you’ve funded your kids’ college educations by showcasing the local florists’ special on clitoria. I think you should own up and tell your wife. Before she insists you quit, let her know that will mean she has to return to her job, and you’ll all be eating spaghetti for dinner for the foreseeable future. The kids only really need to know that dad makes his living as a Web designer (which is true, just as Tony Soprano really was in waste management). Regardless, your letter has just done a great service for struggling freelance Web developers everywhere—expect your competition to heat up.

—Emily Yoffe

From: Help! My Family Has No Idea All Our Money Comes From Porn Sites. (September 25th, 2014).

Dear Prudence,

I love to travel, and really enjoy getting away for the weekend whenever possible. However, my boyfriend of four years has put a real damper on this for me. He seems obsessed with the idea of my flashing truckers when we are on the road. He will pull up beside an 18-wheeler and slow down, expecting me to show off the goods. This makes me very uncomfortable. When I refuse, it turns into a huge fight and he ends up not speaking to me for days. He claims that he does so much for me every day and he can’t understand why I can’t do this thing for him. It has caused a lot of ridiculous fights between us. What can I do?

—Road Trips

Dear Road Trips,

 I like Dan Savage’s formulation that people in sexual relationships should be GGG—Good, Giving, and Game. That is, good in bed, generous sexually, and open to exploring the corners of their beloved’s erotic life. However, if being GGG on a road trip means you end up as road kill, then it’s time to bow out of engaging in your boyfriend’s fantasies. It doesn’t matter if on a daily basis your boyfriend cooks you Michelin-worthy meals and then massages your feet. He gets turned on by your exposing yourself to strangers driving a rig who if they get distracted could squash you like a bug. The answer to your boyfriend’s request is very firm, “No.” If that causes him to stop speaking to you, then you need to extend the silence to forever because he’s simply a creep.

—Emily Yoffe

From: Help! My Boyfriend Demands That I Flash My Breasts at Truckers. (September 30th, 2014).

Classic Prudie

Recently one of my favorite cousins died unexpectedly. My girlfriend and I went to lunch with him and his partner about a week prior to his death, and it was her first time meeting them. Her birthday is coming up, and we’ve planned a small party. In an effort to reach out to my cousin’s grieving partner, I invited him to the party without consulting my girlfriend. Now she wants me to disinvite him and tell him the truth about why. She says she doesn’t want his grief to ruin her happy day. I take full responsibility for being insensitive in not asking her permission first, but how in the world can I disinvite him without hurting her feelings?

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