Dear Prudence

My Friend Loves to Talk About My Past Drunken Racist Comments

Should I tell my boyfriend and new boss about my mistakes before she does?

A finger pointing at a white woman covering her face in shame.
Photo illustration by Slate. Photos by Getty Images Plus.

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Dear Prudence,

Recently I started working at a great company that champions diversity. I also recently started dating a guy who shares those values. But I feel like a fraud. Several years ago, I had a bad habit of getting drunk and stating my poorly thought-out opinions. Twice I said racist, bigoted things without realizing they were racist and bigoted. I no longer do this, and most of my friends knew that these moments did not reflect who I am or what I believe in. They were willing to sit me down and talk about why I said those things. I’m eternally grateful for that. My stomach still churns when I think about what I said.

My friend “Janet” was present for both episodes and wouldn’t stop shouting that I was a racist. My friends have tried to talk her into leaving it in the past, which she agrees to, but if she drinks too much, she always brings it up. Shortly after I got my new job, I attended a work function at a bar that Janet also happened to be at. She tried to shoulder her way in and “set my bosses straight about how I was.” Luckily, a friend stopped her. I was so scared of what that could do to my career. She hasn’t met my boyfriend yet, and I’m worried about what she could do to his opinion of me. I’m terrified right now that she is going to completely ruin my life. But part of me wonders if I deserve it for what I said. Should I come clean to my bosses and boyfriend to get ahead of this? Or should I just wait for her to blow everything up?

—Do I Deserve This?

I’m not quite sure where to begin, so I’ll start with the easier answers and work my way up. Yes, talk to your boyfriend about your history of getting drunk and saying racist things. Tell him about how your friends challenged you, how you may have changed your relationship with alcohol in the intervening years, how you came to understand why what you said was racist, and what steps you’ve taken in your life to make sure you don’t repeat that old behavior. That’s not just important to “get ahead” of Janet, but because it means you’ll feel more deeply and meaningfully known by your boyfriend, and vice versa.

I don’t know how close you are (or used to be) with Janet, but you do seem to count her as a friend. Have you ever had a sober conversation with her where you acknowledged that what you said was out of line, where you’ve offered a sincere and well-thought-out apology for the way your drunken racism affected her, and where you’ve listened to her side of the story? It sounds like you’ve mostly just flinched away from her in the years since your last outbursts, and while you two may never go back to your old closeness, I think it would be meaningful—not in the interest of containing her, but in squarely owning up to what you’ve done in the past and committing to a new way of life in the present. You can be truly sorry for the way you’ve acted, and some people might not personally forgive you or ever amend their former opinions of you. That’s one of the painful realities of being alive, I’m afraid.

Without knowing more about the nature of your job or the dimensions of your former racist outbursts, I don’t feel qualified to make a ruling about whether it’s appropriate for you to talk to your bosses. But even if your worst fears came to pass and you were let go, I don’t think that would ruin your life. It would be a painful loss. You would feel embarrassed, and it might take you a while to find another job in a different line of work. But you would still be able to make good choices, to behave in a way you can be proud of, and to reach out to the friends who’ve already demonstrated a great deal of love and compassion for you.

Dear Prudence,

I recently found out my live-in fiancé was cheating for several months while I’d been traveling for work. He’d been cheating with one of his co-workers; I found out from this woman’s husband. My partner claims they had just broken up and that they were both working on a plan to tell us. I was devastated and moved out immediately. I’ve seen a therapist, started on antidepressants, and canceled our wedding plans. It’s been almost two months, and we are still speaking, sometimes amicably, sometimes not. Thanksgiving was especially hard, and I found myself really leaning on his friendship. Other times, when I’m upset, all I can say to him is to list the ways he’s hurt and wronged me. I feel like he’s robbed me of a future together where I get to be a wife and mother. Is it wrong to consider taking him back? He seems extremely apologetic and has taken a lot of steps toward bettering himself (therapy, cutting off contact with this woman, being honest about what happened and his own shortcomings), and I could see myself possibly trusting him again in the future. Is it foolish to imagine we could be happy again one day, or should I thank my lucky stars that we had no mutual property or children and hop back in the dating pool?

—Rethinking Breakup

I think before you give your relationship another chance, you should consider giving this breakup another chance. I understand it can be really painful to cut ties with someone you loved and trusted, but it’s barely been two months, and you haven’t ever really cut those ties. (Also, his line about planning to tell you is absolute nonsense, and I hope you’re not including that as evidence that he’s currently being honest about his shortcomings. He may be trying to get honest now, but he wasn’t being honest at the time.) Yes, you moved out and canceled your deposit with the florist, but you haven’t had real emotional distance from your ex. You haven’t gone through a significant period of time without going back either to yell at him or to ask him to comfort you. I don’t know if someday the two of you can try to reconnect and rebuild your old sense of trust. It’s possible. But I think first you should give your breakup a good-faith effort. See if you can go for six months without speaking to each other. Find other ways to work out your resentments, your fears, your hopes, your frustrations, that don’t involve trying to have it both ways. If you still miss him in six months and he’s continued with his therapy and program of self-improvement, you can revisit the subject then. But it doesn’t sound like you actually feel secure or safe around him right now, just sad and unhappy at the prospect of really admitting to yourself that you two are truly broken up.

Dear Prudence,

My sister has a large family of in-laws and has developed a regifting habit. Usually it is no bother—almost everyone likes soaps or body wash. But she and her older daughters have gotten lazy about it. For her latest birthday, my 12-year-old got a poorly fitting sweater, a purse with a broken zipper, and other obviously used items. She grew upset after the party and showed me her cousin’s Instagram accounts where the “birthday” gifts were used by them. My sister and her husband make good money, and her girls get a generous allowance. I am not sure where the cheapness comes from, but it hurts. My daughter puts a lot of thought into the gifts we send her cousins. It crushed her to think she is an afterthought to them. How do I talk to my sister about this? She is prickly since her oldest son got into trouble with the police. Should we just tell her to give gift cards now?

—Bad Gifts

Let’s leave room for the possibility that your sister isn’t just doing this out of indifference but because she and her family are struggling more than you realize. When people are trying to save face, especially financially, they can often get defensive, prickly, and avoidant. I think you can mention this to your sister once. Tell her that the gifts her girls got your daughter were broken and worn-out and that you wanted to check in and make sure everything was OK with her. Ask if there’s anything you can do to help. Be prepared for her to not open up right away or for her to decline to take you up on your offer. She may simply get defensive and tell you to mind your business. In that case, leave it alone, and have a talk with your daughter about graciously accepting gifts you know you won’t use and then discreetly getting rid of them afterward. Even if her aunt and cousins are acting oddly, she can still be friendly and polite.

Catch up on this week’s Prudie.

More Advice From Care and Feeding

We moved to a new state and a new school this year, and I am not sure if I should do or say anything about my first grade daughter’s teacher. I’m about as liberal as you can be, and our first-grader’s teacher is … not. She has sent the kids home with lanyards that read “God is Great,” and it’s a public school. I’m not religious, and I am very uncomfortable with this kind of thing. The school is also hosting a Christmas pageant (where the songs will almost all be nonreligious, but still).

I don’t know what to do. At our old school, I would have no problem saying something because I knew the game and the players. But here, I’m friendless and unsure if rocking the boat on this issue is a good idea. Do I say something to the teacher? The principal? Someone on the school board (it’s a very small community)? Or do I just let it go?