Dear Prudence

Help! I Set up a Co-Worker and a Friend on a Blind Date. Her Drink Order Ruined Everything.

She orders what she wants.

Woman sipping out of a straw.
Photo illustration by Slate. Photo by PeopleImages/iStock/Getty Images Plus.

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

Dear Prudence,

I (a married woman) just set up a single male co-worker and a single female friend of mine on a blind date. He’s a sharp guy who’s traveled the world and knows all about fine foods, wines, classical music, designer labels, etc., and she’s a stunningly beautiful and intelligent artist. I really thought they’d make a great couple. Immediately after their date, my friend thought it had gone well and was very excited. On Monday morning, I asked my co-worker, and he said my friend was attractive and a nice person, but he wouldn’t be asking for a second date.

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My friend has been bewildered by her difficulty in finding a steady relationship, so I pressed him as to why. He told me they went to a swanky bar, and she—wait for it—ordered a plain glass of milk. He found this so clueless and childish that he couldn’t imagine being with her. Now my friend is neither a big drinker nor a teetotaler—just someone who’s going to order what she wants without worrying about what others think. Should I tell her why she won’t be hearing from this guy again, so she can reconsider ordering milk on dates in the future? Should I tell him how ridiculous he is for judging someone for something so petty?

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—Dairy Disorder

Dear Dairy Disorder,

I firmly believe that if a man is really attracted to and interested in a woman, she could order a glass of French onion soup and he’d be fine with it. This was not the guy for your friend. She does things that he finds clueless and childish. She doesn’t want to be in a relationship with someone who feels that way about her—or someone who doesn’t think her beauty and intelligence make her clueless and childish behavior sort of charming. She should not hide who she is or what she likes on dates. The idea here is not to fake a personality so she can be paired up with someone who you think is a fit for her. It’s to keep being herself until she comes across someone who is actually right for her.

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Dear Prudence,

Our 18-year-old twins are coming home for their first Thanksgiving break from their out-of-state college. We visited them a few weekends ago, but it was a quick trip and their friends and friends’ parents were often with us. We really want this visit home to be restful and relaxing before they go back for finals. Additionally, I have a million questions about things that have happened (roommate drama, first romance, etc.) that we’ve barely scratched the surface of in FaceTime calls. We are a close family, but I want to respect their new status as young adults living independently and my tendency to get intense and nosy. For what it’s worth, I started therapy before their senior year in high school because I saw that I was becoming more intense as their leaving the nest loomed nearer and they were withdrawing. Do you have any suggestions for encouraging connection and conversation while still respecting their autonomy?

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—Nosy Mom By Nature

Dear Nosy Mom,

This is so sweet, and really reads like the letter of someone whose therapy is working well. It’s also a situation where transparency about how you’re feeling would go a long way. Let your kids into your thought process by saying something like this before they arrive: “We can’t wait to see you! I love you both so much and I have a million questions but I promise I’ll try not to get too intense and nosy. I know you’ll want to rest and see friends but could we set aside an afternoon to spend time together and catch up?” I think it will mean a lot to them—and help them see this stage of life from your perspective—if you are honest about your feelings, your needs, and even your insecurities. This could represent the beginning of a new, adult relationship and will come in handy in so many other situations in your future.

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If they agree to talk, a great time to do that would be on a long drive or walk. Something about being side by side instead of across from each other lends itself to opening up without feeling like you’re in a job interview.

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How to Get Advice From Prudie

Submit your questions anonymously here. (Questions may be edited for publication.) Join the live chat every Monday at noon (and submit your comments) here.

Dear Prudence,

My parents divorced when I was young, and my mom is an alcoholic who goes in and out of my life. Right now, she’s out (my choice). My dad married my awesome stepmom “Starla” when I was 10, and after a hard early transition, she’s been an amazing loving mom to me, even in my hardest teenage years. My dad is one of those fathers who works and pays the bills but wasn’t as involved as my friends’ dads.

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Last week, my dad announced that he and Starla are getting divorced. I was shocked and really sad, and even more when I learned it was because he was cheating on her with my mom, and they are getting back together. I’m so angry and sad that he would choose her over Starla, especially because she hurt me so much. I feel like I’m being sliced out of my own family, and I want to cling to Starla for reassurance, but I don’t know how to talk to her without being crazy. She’s been calling and texting but I’m scared to answer. I’m on a waitlist for a therapist at my college, but it will be at least a month. What should I do?

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—21 and Confused

Dear 21 and Confused,

Talk to Starla! Cling to her! Treat her like the mom you never had. Tell her how hurt you are by your dad’s decision and how important she is to you. Be open with your parents about the fact that she’s an important person in your life. Biological ties and official titles aren’t everything. If I had to make a prediction, I’d say that years from now, your mom and dad will have split up again and will be just as unable to show up for you and when it comes to holiday celebrations, your wedding, or the birth of your child, Sharla will be the one who’s there. You said it yourself—she’s been a loving mom to you. Let her continue to be.

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Dear Prudence Uncensored

“I do have strong opinions about beverages but here’s my thing: If you really like a person, you’ll let it go.”

Jenée Desmond-Harris and friends discuss a letter in this week’s Dear Prudence Uncensored—only for Slate Plus members.

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Dear Prudence,

I’ve been invited to a family wedding this summer: so far, so good. It has a clear dress code: yay! But here’s where the problem comes in: “For gentlemen, this means suits. For ladies, that means nice cocktail dresses.” Prudie, I am a gender nonconforming queer woman and my knee-jerk reaction is damned if I’m buying a cocktail dress so as not to shock the bride’s bejeweled aunt or whoever. Part of me even derives a little thrill from the idea of shocking the stuffy rich conservatives (this is an area with, uh, a lot of them.) But it’s a dress code. If I have a nice suit picked out, am I still a jerk for wearing it?

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—Breaking the Rules (And the Gender Binary)

Dear Breaking the Rules,

Wear the suit. The dress code can be translated to, “Suits for suit-wearing people and dresses for dress-wearing people.” It just wasn’t communicated with the fact that we live in the year 2023 in mind.

Give Prudie a Hand in “We’re Prudence”

Sometimes even Prudence needs a little help. This week’s tricky situation is below. Join the conversation about it on Twitter with Jenée @jdesmondharris, and then look back for the final answer here on Friday.

Dear Prudence,

My mother-in-law has always been difficult, but right now she is driving me to drink. She is in her 80s and could no longer live alone after two bad falls. She needed round-the-clock care that her family couldn’t provide (we collectively have been paying for outside help for years). The retirement home is very nice with lots of activities. It is located 15 minutes from our home so our family could visit. Now I am wishing we went with the ones near my sisters-in-law.

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My wife visits twice a week with our 5-year-old and calls her mother every day. And all my mother-in-law can do is inflect misery all around. She wants to die. They should have left her on the floor of the house to rot. She could be in heaven with her husband, and instead, she is here. She hates it here. She just wants to die. She has gone on these rants in front of our 5-year-old. My wife has come home crying and our child is hysterical because they don’t want grandma to die. All of this is taking a serious toll on my wife’s mental and physical health. She feels so guilty but there was nothing to be done. The doctors say my mother-in-law is mentally astute and has been put on antidepressants. My sisters-in-law visit and call when they can but my mother-in-law doesn’t feel the need to inflict all this misery on them. My wife is just the lucky one.

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I have already put my foot down about taking our child on these visits. Two hysterical visits are too many. My wife tells me I need to support her here. I am trying to but I can’t stand to see her in such pain. Help!

—Misery

Dear Prudence,

Five years ago my brother’s best friend, Harry, married my best friend, Petra. During the honeymoon, he went rock climbing, fell, and damaged his spine significantly. He’s used a wheelchair since. That all sucks and changed both of their lives a lot, but they stuck together and are now trying for a baby.

That’s great. I think they’d be good parents. I just don’t want to know about it! I’ve known Harry since I was 6 and Petra since we were 10, I don’t want to think about their sex life. I assume they have one and that’s all that matters. But Petra wants to tell me the details about everything, from sperm counts to injections. It’s just too much AND it feels like I know stuff Harry would be mortified about.

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I know that you’re going to say, “Just tell her you’re uncomfortable.” And that’s fair enough. I just feel guilty because I know she’s no one else to talk to about this. She doesn’t have many close friends other than me and her parents are on an information diet about her life since they wanted her to break up with Harry after the accident. So if not me, then who? So, how do I find a balance between “Eww, TMI” and being a supportive friend? If I can draw a boundary line, where should it go to accommodate my discomfort and her need to talk through a stressful time?

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—Uncomfortable

Dear Uncomfortable,

This is kind of weird! Sperm counts and injections are really not super sexy content. This is medical information we’re talking about. Do you freak out when able-bodied people mention, “We’re trying for a baby”? We all know what that means but come on, it’s a part of life. I doubt she’s telling you stories that include “And then we took our clothes off and got into bed…” Really reflect on whether this is about the sex or the idea of your brother’s best friend being a wheelchair user who has sex. If you must, just tell her, “I’m here for all the details about your doctor’s appointments, test results, and procedures but make sure you spare me the details of your actual sex life—it’s ridiculous but I feel strange thinking about my brother’s best friend in that way. Anyway, do you need any help with your injections?”

Classic Prudie

My wife and I are finally at a point in our lives where we are ready to adopt children, as we’ve always planned. I love the idea of being a mother and always thought I wanted this when the time and circumstances were right. Well, the time and circumstances are right, and now I’m terrified. I keep stalling the conversation whenever my wife brings it up, but I don’t want to do that to her for long.

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