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: Welcome back, everyone! Tell me about all the confusing, annoying, and troubling things that have happened so far this year.
Q. Owning Up to High School Offenses: I am a 25-year-old woman, and I have been in a relationship for almost three years. I don’t have any friends in my hometown where I still live, and I have never told my partner why.
When I was 17 years old, I had a close friend, Lily, who came out as pansexual, and I decided to ask her out. She turned me down kind of indirectly, and I was too socially clueless to realize this. I tried asking her to hang out more after that, but eventually, she stopped talking to me. Soon after, the school guidance counselor told me that I had to leave the school temporarily, but she wouldn’t explain why. I found out on social media that Lily was saying that I had stalked her. Lily was close with my other friends, and they all stopped talking to me after the incident. After about a week, I was allowed to come back to school. The next year, I went to college out-of-state and made new friends, but I never reconnected with anyone from high school. I accept now that I was completely at fault in this situation and I should have just left Lily alone, but it took me a long time to get over losing my friends and being kicked out of school without an explanation. It was only when I was around 21 that I was able to see the situation clearly and accept responsibility for what I did, which helped me to stop being angry and feel more empathy for Lily instead.
I have told very few people about what happened with Lily, even though it hugely affected my life, and I still get bad dreams sometimes when I’m back in high school and everyone is angry at me. I want to tell my current partner about this, but I’m not sure how I would tell them, and I feel bad for withholding this information from them for so long. What should I do? Is this something I should have told them already?
A: Either something’s missing from this story and “I tried asking her to hang out more” involved calling her 93 times in a row and showing up repeatedly at her front door OR you did nothing wrong and this was a massive overreaction by Lily, and a potentially homophobic one by the guidance counselor and your friends. I don’t have enough information to decide what really happened back then, but whatever took place is part of your story. I don’t think you owe your partner this information (though it might indeed be helpful in understanding your current social situation), but a great test of whether they’re someone who makes you feel safe—and whether they’re a good fit for you—is if you feel comfortable sharing it.
Q. What Should I Do?: I need some advice about a platonic male friend. I don’t have long to live and he and I had promised to look out for each other. I pay him to help me with errands and transportation since I was injured by a Semi. He promised to keep in regular touch with me and help me out. I promised to pay him for his assistance and offered to leave him my worldly assets when I die. Most recently, however, he doesn’t check in on me and periodically leaves a text or voice text. No direct interaction. I am generous, independent, and not at all demanding. I want to renege on my promise to bequeath my possessions to him. I feel that he broke our pact and never wants to address my feelings. Should I change the arrangement?
A: I’m so sorry your friend broke his promise to you, especially during such a difficult and scary time, when you’re at your most vulnerable. To almost-ghost anyone is rude. To do it to someone who has limited time left on this Earth is especially heartless. Yes, absolutely renege on your promise, and think of someone else to leave your possessions to. I hope there is another person who’s reasonably close to you or who has been kind to you in the past. If not, maybe you could think of an individual or organization for whom these belongings could make a real difference. But don’t spend too much of your precious time talking to your friend about this decision or even thinking about him—he’s not worth it.
Q. Late Night Chats: I was wondering if it was just me or not, but would you find it weird that your significant other was hanging out/talking to another female late at night (also the girl has a boyfriend) without you knowing and exchanging numbers?
A: No, it is not just you and yes, I would definitely find it weird. Years ago, a wise friend said to me, very simply, “Jenée, you deserve a boyfriend who doesn’t get other women’s phone numbers” and it was a revelation at the time! Sharing that in case you need to hear it, too.
Q. Caught Between a Friend, a Boyfriend, and a Hard Place: My close male friend, “Derek,” turns into a different person when my boyfriend, “Sam,” is around. I became close friends with Derek and later his whole friend group in the last few years. I have a lot of affection for Derek and we have a lot of shared interests but have never had any attraction to him. I started dating “Sam” within the last year and introduced him to Derek and his friend group within the last few months. The two times I have had Derek and Sam in the same place, Derek acts like a low-key jerk. He makes jokey fun of Sam and seems to take inordinate pleasure in things like beating him at board games. I don’t think Derek is understanding he’s going too far. His usual relationship with his friends is one of mutual making fun of each other, but I feel it’s inappropriate for him to do this to my boyfriend, who he’s only hung out with twice. My boyfriend is very cool about it and just thinks Derek is jealous of him, which I suspect is the case. My birthday is coming up and I’m really stressed about interactions between them, to the point where I told Sam to just stay out of Derek’s way to preempt any sarcastic jabs. Should I let Derek have “strike three” and see if he behaves, or talk to him in advance?
A: Well, unfortunately for Derek, you picked the right guy. Your attraction radar is good! Instead of the mean, insecure guy who, yes, almost certainly has a crush on you, you chose the confident guy who can see why someone is being an asshole to him and not take it personally.
It sounds like Sam can really hold his own, so I don’t think you need to do anything else to protect him, other than tell him to be sure and let you know if things change and he feels like you’re bringing him into environments where he’s being bullied or facing abuse. In the meantime, if you find yourself not enjoying these hangouts because of the jabs and nasty comments you might consider pulling back from group events with Derek. Also, reevaluate your friendship with him. Because antagonizing your boyfriend is not a good way of showing you that he values it.
Re: Q. Owning Up to High School Offenses: Oof, regardless of the details, it’s clear that you carry a lot of shame about this incident. I know Jenée is paid not to recommend therapy, but I think it would help to work through this, especially as you’re still feeling that guilt. In those sessions, you can also talk about a way to discuss with your partner that is honest but doesn’t re-traumatize you. Please remember too that we as a society give kids HORRIBLE advice about how to handle crushes and you may have been led astray by those messages. It’s time to forgive yourself.
A: Yes to all of this! I love the compassion for LW’s former self and the push for forgiveness. Whatever happened, it shouldn’t remain a massive source of shame.
My relationship ended because although we were still in love, we were at an impasse where children were concerned: He had gone from “maybe” wanting them to 100 percent committed to living child-free. I have always wanted to be a mother, so we split amicably and I moved back to where I’m from on the other side of the world. Then, two weeks ago, I discovered I’m pregnant.