If you enjoy the column below, please subscribe to my newsletter! You’ll get each new issue in your inbox for free. I love having new email friends.
And if you’ve got a problem you’d like me to solve, send it in via my anonymous form. Let’s open some letters!
I dated a guy in high school. Broke up and years later he’s dating a girl we went to school with. She can’t stand him talking to me but he keeps messaging me and even asking some very not-okay questions (asking for pics and whatnot). Do I tell her when I know it’ll end their relationship?
Well, let’s start here: You should definitely tell your ex to stop sending you those messages. Perhaps you already have, but since you didn’t mention it in your letter, it’s worth a callout. Make sure this guy knows you’re not playing ball. It doesn’t even need to be a conversation, if you’re uncomfortable having it. This is why humans evolved to have a block button.
As for whether you should tell the girlfriend, you have my blessing as long as you’re prepared for the fallout. I certainly don’t care about protecting the guy, but I do care about protecting you. So to that end, I am going to name three potential downsides to telling her. I’m not saying these things will happen, but they’re possibilities worth preparing yourself for:
1. She doesn’t believe you: She might call you a liar or twist the story to make it your fault. Screenshots might help you here. But for the delusional, facts are not particularly compelling. This is actually how we got our president.
2. Your ex gets angry: Not that it necessarily matters, but he will likely be mad at you for exposing him. It can be intense to be the target of someone’s anger, especially when you’ve done something that impacts him quite personally. Would you be safe? Is this guy nuts? Would he retaliate in some way? If there’s any risk of physical or emotional harm coming your way, I’d disengage from this. Your first responsibility is to yourself and your well-being.
3. They break up, and you feel bad about it: In theory, breaking up a toxic relationship is great. In practice, it might feel less than great. You might be saddled with feelings of guilt, doubt, or regret. Of course, I’m not saying you would deserve those feelings — I just want you to be prepared for them. They’re human.
Best case scenario, this girl believes you, dumps the guy, and you become best friends who maybe even get matching tattoos. I hope that’s what happens. But prepare yourself for the worst case scenario, too. If it’s something you’re certain you can handle, go forth and tell her. If not, protect your peace.
I matched with a man on Hinge. After a few days of chat we agreed on a date. Then he sent me a link to a New York Times quiz about current events. He said he only dates women who are “knowledgeable and informed” and wanted to know my score. I thought he was joking but he was not. I did indeed pass the quiz, but I’m grossed out. Should I go through with the date?
I just wrote and deleted a whole paragraph explaining why you should not administer a written test to your date, but it felt akin to explaining why you should not hit your date with a car. So, can I just leave it at no? Because no. You should not go on that date.
Here’s a drawing I did of a frog in love with some olives.
For more drawings, follow me on Instagram. Back to the advice!
My friend has fallen in love with a coworker she shares an office with and this coworker clearly does not like her back. She decided to profess her love to him, and instead of him saying no, he said maybe to protect her feelings. The whole thing was handled poorly on both sides and has resulted in too many “talks” between the two of them that just sound like they are rehashing the same thing over and over.
My issue is, she won’t stop talking about it. The first few times she shared with me, I comforted her and gave advice, but as time went on, I got tired of it. Then another friend we share lost a family member, and she still chose that time to launch into a long rant about everything this guy did that drove her batty that week, and how this is the worst three months of her life. We both feel tired of this. It’s playing out eerily similarly to her previous relationship, and I am sick of hearing that a boy not liking her back is her worst experience! How do I tell her to move on and stop trying to convince him to like her?
Getting your friend to move on from this guy feels like the wrong goal here; your actual issue is not her boy problems, but the way those problems suck the oxygen out of every room. Sure, you can name the patterns you’re seeing: This feels like your previous relationship, you’re investing in the wrong guys, etc. But if this is a real habit for her, you’re unlikely to be the one to break it. You’ll be met with the typical resistance: You just don’t get it, this guy’s different, yada yada. It is very likely a dead end.
Instead, focus the conversation on the thing that actually impacts you: The way she dominates every conversation with these woes. I’d say something like: “Jessica, as I’ve told you before, I really don’t think Bryce is the guy for you. But more concerning to me is how this seems to dominate your focus at all times, even when others need support.” The story about your grieving friend would be useful here, because it is so indisputably bad. Name what you’re observing. See what she says.
Will it work? I’ll give it a 50/50 chance. Some of what you’re describing sounds like good old-fashioned narcissism, and that’s tough to fix. But you’ll be showing her grace by calling out the behavior and giving her a chance to change it. Whether she takes that chance is up to her. You don’t need to give her more than one.
Don’t cry because today’s column is over — smile because it happened. But before you go, I hope you’ll subscribe to my free newsletter! Next week’s issue has a juicy theme: Friend group drama. I’ll be answering three questions from letter writers whose friend groups are in crisis. Subscribe so you don’t miss it!
And don’t forget to send me your problems via my anonymous form. See you next week!