Dear Prudence

Help! I Planned a Big Birthday Surprise for My Roommate. Now She’s No Longer Speaking to Me.

Read what Prudie had to say in Part 1 of this week’s live chat.

Woman in a towel looking scared.
Photo illustration by Slate. Photos by Getty Images Plus.

Dear Prudence is online weekly to chat live with readers on Mondays at noon ET. Here’s an edited transcript of this week’s chat.

Jenée Desmond-Harris: Hey friends! Happy Slate Advice Week to those who celebrate (I do!) Let’s get started.

Q. Bad Surprise: I’m in college living in a double dorm room with a close friend. Her birthday was last week and I organized a surprise party for her that went about as badly as humanly possible and I don’t know what to do about it now. I knew that she was going out to dinner with her parents and she told me she expected to be back around 9 p.m. I pretended I might be out with friends and told her to text on her way in case she wanted to join us. A group of about 10 of us gathered at a friend’s room down the hall to get everything ready. She texted she was going to stop at our room but then might come out. Perfect, we all went into our room, hid under the beds and the desks, and basically just crammed wherever and turned the lights out.

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A couple of minutes later, the door opens, the lights turn on, and before we can even jump out she drops the towel wrapped around her. She’s completely naked as we all jump out. Apparently, she was already back when she texted me and was showering when we got into position. She burst out crying and started screaming at me and we all just very awkwardly left. She still won’t really talk to me despite my many apologies and I can’t really blame her. Is there anything I can do to make up for this? I want my friend back but am scared I ruined it for good.

A: This was such a horrible mistake but it was also such an innocent mistake. You can both feel very sorry about what happened, and forgive yourself. The way forward might be to accept that you (in the course of being a really nice person) caused enormous embarrassment for your friend. And that embarrassment might be so intense that she’s unable to forgive you right now. Just be patient. Don’t annoy her. Don’t try to explain to her why she should forgive you. If she ever gets there (and I think she will) be gracious and don’t hold her period of being mad at you against her.

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Q. Too Torn to Choose: I have two dear friends, one who I would call my ride-or-die bestie (let’s call her “Tracy”) and another, (“Edith”), someone who I became extremely close with in middle school. Before I met Tracy, Edith was my closest friend. We could understand each other so well, get along, and have similar interests. I can distinctly remember thinking, “We’re so similar, I may as well BE her,” many, many times.

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But then Tracy enters. We click, just like Edith and I did. So much so that I ended up sharing things that I never could have ever thought of with Edith; for example, my journey of self-harm and recovering from it. Within just a couple weeks of knowing Tracy, I let her in the lowest of lows in my life. I think that’s why we’re so close now, because we confide such deep things so early on, allowing us to make a connection of mutual trust and love that we wouldn’t have made otherwise.

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I didn’t mean to leave Edith behind. I didn’t ghost her or anything, we’re still pretty close, but when I would have been going to Starbucks or calling her, I do that with Tracy instead. I hear all the time that friendships and people change, especially in high school, so while I suppose it’s not abnormal that this has happened, I still feel guilty whenever I think about it. I feel like I owe something to Edith, so when I saw her request my name (you can only enter one person, and to have them as your roommate they must request them back), I immediately felt the obligation to put her name down. But the thing is I was going to put down Tracy.

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I know it seems like such a trivial thing, to worry over roommates, but I know that whatever choice I make will end up having somebody unhappy—if I put down Tracy instead, it’ll tell Edith that I don’t “want” her and leave her feeling hurt and excluded, which will be painful since I was right beside her when she put down my name. But I know I’ll have a much more memorable and fun time with Tracy and enjoy this trip so much more. The deadline for the form is only in a couple of days, and I’m already stressed about who to choose because I can tell whatever choice I make will impact both friendships drastically.

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A: Choose Edith. I know. You don’t want to. But, two things:

A) Getting left behind by a best friend in high school (even if that best friend simply found someone who was a better fit) can be a horrible experience that hurts someone for a long time. You don’t want to be the person responsible for Edith’s misery. Not like this. There’s something to be said for loyalty, and I think you owe it to her.

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B) Edith wrote your name down first! So you have an easy out with Tracy: “I know we’re really close and I love hanging out with you but I just learned that Edith put my name down as her roommate. She and I go way back and have a lot of history between us and I think the right thing for me to do is to choose her too. Would that be OK with you?” As someone who you’re really opened up to, and someone with whom you share so much trust and love, Tracy should understand this.

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And then please, hang out as a trio. The roommate assignment only dictates where you sleep. You can spend all your days together, until the moment you’re ready to close your eyes. If you and Edith are so incredibly similar, she and Tracy will love each other too. By the end of high school, the three of you could be inseparable.

It’s great to have more than one friend at a time. It’s wonderful to be a person who connects people. It’s almost always a good choice to err on the side of being inclusive and kind, and to look out for people who may be at risk of getting hurt. All of this is especially true in high school when things can get so rough for so many kids. And in this situation, you can do what’s right without giving up any of the fun you hope to have on the trip.

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Q. Hopelessly In Love: I recently friend-zoned a girl I liked. For reference, I am openly gay and she was not, and I was fine with that. She told me she liked me and I said that I did as well, but wanted to wait because I had just gotten out of a long relationship. She said OK but later texted me and told me she was straight and she has just made a mistake in liking me. However, I still liked her and eventually, we became really close again. About a month ago she asked me if we were just friends. I didn’t want to go through the pain of having her tell me she was just confused, so I rejected her. Now, a month later, I have almost gotten over my feelings for her, but I was having a bad day and she comforted me when I was feeling vulnerable, and all of those feelings came rushing back. She’s a good person, but I don’t know what to do.

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A: Sadly, I think the collective communication skills and emotional maturity in this letter are not enough to sustain a relationship. You’re both all over the place, wishy-washy, a little confused, and will probably just terrorize each other repeatedly if you get together. Look elsewhere for love.

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Q. Missing Home: Is loneliness on holidays enough of a reason to move home? My husband and I have lived more than 1,000 miles from each of our families (who themselves live 1,000 miles from each other) for more than five years. We both have great jobs doing what we love, a busy social life with wonderful friends, and an almost 2-year-old child. Moreover, my family is able to visit several times a year, though we can only afford to travel out of state once or twice per year. The only times we consider moving to be nearer to either of our families is during the holiday season or our child’s birthday. We both have very warm memories of the holidays with our families, including siblings, cousins, aunts, uncles, grandparents, etc., and wonder if we’re depriving our child of the same. Neither of us is particularly keen on living in our home states, and it may require getting jobs in fields we’re not trained in or don’t love as much. Is it worth it for our child to grow up near family?

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A: Nope. Don’t do it. You’re happy where you are and it sounds like a move could throw your life into disarray and decrease your happiness in ways your family couldn’t help with. Instead, think about creative solutions for spending more time with the people you love during the holiday season. If your work allows, could you stay for a full month and work remotely every year? Would it be worth it to look for a new role that would allow this? How about a home swap to cut down on costs and let you stay even longer? What if you were to create new traditions like FaceTiming every evening as your kid opens their advent calendar for that night? Or a cookie exchange via mail. Or making photo books of the time you do get to spend with family and reading them throughout the year to really get the most out of your time together. What you want for your kids is really to feel the love of their relatives during the holiday season and make good memories. You can accomplish that without a moving truck.

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Re: Q. Bad Surprise: You’ve apologized, you’ve tried to talk to her, you have probably figured out never to do this again to someone whose feelings about surprises are unknown to you, etc. There’s not much more you can do. Let this be a life lesson: The silent treatment, no matter how angry you are, is a terrible way to interact with people, so make sure not to do it yourself. Learn how to express your feelings, even when you feel too angry to do so. You may be stuck with an angry roommate for the next several months. We all had bad roommates—I had one who had such terrible body odor that I had to open the windows in January in Wisconsin, 45 years ago. This will all be a funny story one day. The body odor was funny once we went our separate ways.

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A: Such a good point. I think before you throw someone a surprise party, you have to, a few months before, discreetly ask how they feel about surprises. And yeah, our letter writer may be stuck with an angry roommate for a while and that sucks. Probably not as much as the body odor situation did, though.

Re: Q. Too Torn to Choose: Even the closest of friends are sometimes not the best roommates. When I was in college, my sophomore roommate told me she had to move out (our schedules were different: She was an early bird, and I was an insomniac) to save our friendship. I was hurt for a while but completely understood. And she was right. We could be best friends but we couldn’t live together in the same room.

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A: This is a good perspective, but I don’t think the letter is about roommate compatibility as much as it was about friendship and potential hurt feelings.

Re: Q. Missing Home: While I love Prudie’s idea of looking into working remotely, make sure you look into it properly with your company. If they don’t already have employees in that state they might not let you do it, as having to set up taxes for that state can be too much of a headache. On Ask A Manager, a letter writer’s boss agreed he could work remotely for three months. He went ahead, found an apartment to rent, etc. Then the boss came back and said he was sorry but HR told him that wouldn’t be possible for the tax reason.

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A: That sounds like a nightmare! Definitely follow this advice, LW.

Catch up on Advice Week here!

Classic Prudie

 Seriously, the diamond in my engagement ring is way too large! I know this sounds like a humblebrag or the rant of a crazy person, but it is true. My fiancé and I have been talking marriage for a couple of years, and he proposed over the holidays. I said yes of course. He didn’t have a ring and said he was going to surprise me with one. All good so far—honestly I love this guy to the moon and back so I was thrilled. Then two weeks ago he gave me the ring.

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