Dear Prudence

Making Out Like a Bandit

My “friend with benefits” wants to pretend our hook-ups never happened. How do I salvage the relationship?

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Dear Prudence,
I am a female senior in college and am good friends with a guy I’ve known since middle school and all his roommates. He and I have become even closer over the course of our college years. Earlier this semester, we went out for a few drinks and ended up making out back at my apartment. We decided not to talk about it and to pretend that nothing ever happened. A few weeks later, we did the same thing. We tried to pretend nothing happened, but our relationship became so awkward that I began to think that it would never recover. Finally it did, but then we ended up sleeping with each other again. This time, I forced him to talk about it, and he decided that we should “just be friends.” I agreed, and slowly things got less awkward and everything was great again. Until the other night, when I stayed at his place after drinking with him and his roommates. All the people I’ve talked to about it tell me that I should tell him we can’t sleep together anymore and stick to it in order to save our friendship. But I feel like a pattern is developing here, and I’m afraid I’m going to lose my best friend.

—Friends With Benefits

Dear Friend,
A young man and woman get to know each other well, care for each other deeply, and then become physically intimate. It used to be that such a course of events often led to a state known as “falling in love.” Now it’s just seen as the way two members of the gang bum out everyone—including each other—because they suddenly are acting weird. I don’t want to be one of those crones extolling how it used to be; believe me, there was plenty wrong with the dating culture of old. And I truly admire the way your generation is able to un-self-consciously make friendships across gender lines. But your letter is at the heart of what’s amiss with today’s hook-up culture. As you have discovered, there’s been little benefit to you if “friends with benefits” describes meaningless and embarrassing sexual encounters. You may not want to acknowledge it, but it sounds as if your sexual intimacy has stirred romantic longings in you. That’s a normal thing to feel, and it’s painful if not reciprocated. This is why it’s best if sex is more than just the way you tell you’ve finished a drinking game. According to sociologist Kathleen Bogle, author of Hooking Up, once people who’ve only hooked up graduate from college, they do start dating one person at a time, but since some have never even been on a single date, they’re as clumsy at it as high-school freshmen. If this young man is truly your friend, not just a buddy you’ve known for a long time, you should be able to discuss with him that this no-strings sex has hurt and confused you and that it’s hard to pretend it never happened. This discussion does not require a quorum. And as difficult as having such a conversation might be, it will be good practice for that looming next stage of your life.


Dear Prudence Video: Sleeping With My Sister’s Husband

Dear Prudie,
My wife is a prominent businesswoman who is heavily involved in the arts. I am an anti-establishment lawyer. We were invited to a business/social dinner, along with a big-time Republican and his wife, at the home of a local artistic director and his partner. I am a longtime acquaintance of the other four people through my wife, and they all know I am a strong Barack Obama supporter. George W. Bush’s rating as president became a topic, and I said, “He’s so bad, he got a nigger elected president of the United States.” Everyone seemed to think it was funny except my wife, who kicked me. A kick usually suffices, but she has continued to berate me for the past week. I maintain that everyone present was intelligent and highly educated and therefore understood that nigger was meant ironically. She says nigger should never be used in polite company. Polite company bores me. Did I cross the line?

—Doghouse Resident

Dear Doghouse,
If you were my husband, you wouldn’t be in the doghouse—you would have been given back to the Humane Society. You say “a kick usually suffices,” so I assume your wife is frequently embarrassed by these outbursts of yours designed to show your disdain for her “establishment” colleagues and friends. What I find to be a bore, and a boor, is someone who thinks he occupies the moral high ground because he behaves rudely. Your remark was so appalling that I think you should send everyone a note saying that in a misguided attempt at topical humor you made an offensive joke and you apologize for it. And if you drop the adolescent attitude of rebellion, you’ll find decent qualities in the people your wife associates with, and they will be pleasantly surprised to find the same in you.


Dear Prudence,
Recently, while having dinner at my in-laws’ house, my very rude sister-in-law informed me that she was going to feed my 3-month-old daughter sugar-free pudding. I nicely told her that my daughter is exclusively breast-fed and is not ready for solid foods. While I was in another room, I noticed that my mother-in-law was no longer holding my baby. I walked into the dining room and caught my sister-in-law by surprise. She had fed my baby pudding from her finger. This made me extremely angry and upset. When I told her again my daughter is not ready for solid food, she rudely said it wouldn’t hurt the baby. Not only could the sugar-free additives cause an allergic reaction but so could the milk in the pudding. Not to mention that I totally felt betrayed that she would do something that I asked her not to do. I am sure that she didn’t wash her dirty finger before she placed it in my child’s mouth, either. How do I handle this situation when we see them at family gatherings? We constantly disagree when it comes to the way we parent our children.

—Leave My Baby Alone

Dear Leave,
Your sister-in-law must have pudding for brains. While it was unlikely a fingerful of the stuff would hurt your child, what she did was a flagrant and provocative violation. Next time you’re all together, I suggest both you and your husband talk privately to her and her husband and say that while you each have your point of view about being parents, surely you can all agree it’s imperative that you respect the rules on how each of you are raising your children. Say that you expect that there won’t be any more incidents like feeding your child something you have expressly asked that she not. Then keep an eye on your baby and this dope.


Dear Prudence,
I am a twentysomething recent college grad. I live at home with my parents and work in the city. Recently a ton of confusing, frustrating, overwhelming things have happened in my life, including my parents’ messy and vicious divorce and my mother’s failing health and multiple hospitalizations. One of the sunny spots in all this is my wonderful relationship with my boyfriend. However, I am planning a trip to Miami to get away from it all, and I want to go alone. I don’t even want my boyfriend to come. How do I explain this to him without sounding ungrateful or seeming like I’m snubbing him? He wants to be there for me, and I just want space to think … and drink lots of cocktails on the beach.


Dear Stressed,
Can I join you? Oh, I guess that would defeat the purpose of the trip. Yes, it’s perfectly understandable that you would want to just lie in the sun and not have to consider anyone else’s needs for a few days—not even so much as where your beloved wants to go for lunch. Just be honest with your boyfriend. Say the last several months have almost done you in, and if it hadn’t been for him, you don’t know if you’d even be functioning. But explain that right now you are feeling that you’re lousy company and totally burned out. What you need is to get away by yourself for a few days, so you can lie on a beach chair, read junky novels, and not speak to anyone—except him, when you call to say how grateful you are that he’s in your life.


Photograph of Prudie by Teresa Castracane.