Dear Dana: When Should You Break Up With A Friend You’re No Longer Into?

Dear Dana is a bi-weekly advice column for humans who engage in romantic relationships. Please send your dilemmas, issues, conundrums, assumptions, conflicts, anxieties, worriments, obstacles, complications, predicaments, queries, questions, and any other synonyms for “problems” to

Dear Dana,

I met a girl at a party a few months ago and thought we could be friends—I’ll call her Karen. We got along the night we met, but after hanging out with her a few times, I decided I didn’t enjoy spending time with her. Mostly she just seemed to text me when she needed something: a ride to the airport; the laundry in her building was busted and she needed to do it at my apartment; could I watch her cat for a week? At first I said yes, but as these requests went on, I began saying no. Finally I just started saying no to everything she sent my way because I didn’t want to hang out with her. I never initiated hanging out, but she still kept texting me. 

Some additional information: It wasn’t just that I felt like I was being used—she didn’t seem like a good person. She made snide comments about the homeless people in our neighborhood and teased me about some of the things I like. To be fair, I think part of my sensitivity to this is because she made a lot more money than me and seemed to live in a rich person bubble, but still. We had nothing to talk about, and a lot of things she said made me cringe.

Also important info that makes me look not great: We were both new to our city, and I think she may have had fewer friends than me. Ugh, I know. It gets worse. 

The last time she asked me to hang out, I lied and said I wasn’t feeling well. The next night, she saw me out at an event with another friend. I was so clearly busted, and I feel terrible. Should I have broken up with this friend? If so, what was I supposed to have said? Is it too late to reach out?




Dear Frenemy,

Making new friends as an adult in a new city is really, really hard. You’re so excited when you meet someone who wants to hang out with you that you often don’t even worry about whether you like them or not. Who cares if you get along—you finally have weekend plans!

Friendships are difficult to end because, unlike romances, they don’t have fixed starting points. Friendship is nebulous and constantly changing. The framework of a friendship can be set by an initial meeting, but the friendship itself is usually only defined as such after the fact—through a combination of proximity, time, and shared experiences the two of you begin to describe each other as friends, or good friends, or best friends.

People rarely have a “defining the relationship” talk with their friends, and thus it makes having an “ending the relationship” talk incredibly awkward. Why must you have a conversation about ending a friendship if you never discussed starting it? Can’t the relationship just naturally melt away?

When we’re talking about trying to disengage from other people, you usually have two options: soft nos and hard nos. A hard no is just what it sounds like—“Do you want to hang out tonight?” “No, I don’t like you and don’t want to hang out with you anymore.” It’s clear, unequivocal, and unmistakable. It calls out directly your feelings about this person and forces them to understand that you, in no uncertain terms, do not like them. It’s also rarely employed because it’s really, really mean.

A soft no attempts to trade on subtext to get your message across. “Do you want to hang out tonight?” “No, sorry, I’m busy,” can mean either that you’re busy that night, or that you’re tired of this person and don’t want to see them anymore. Those of us with anxiety (my hand is raised) will often interpret all soft nos that we receive as “BTW I hate you,” while those blessed with a unnatural confidence will never see a soft no that way. They’re just busy tonight! Let’s ask about tomorrow!

That’s the thing about the soft no—context is everything. Is your friend saying no for tonight, but then offering up an alternate date? Are they texting you about other things? Do they seem to like you overall but could actually be busy that one night? Then great—calm down, the friendship is still on. But are they refusing your every advance? Are they constantly saying “no” without offering an alternative date? Then they’re probably trying to move away from you without being brutal. They’re trying to let you come to the conclusion that you two shouldn’t hang out anymore. They’re trying to leave the relationship while still allowing you to save face—it’s the other person’s problem, she’s super weird, you don’t like her anyways, time to move on.

But some people hate the concept of the soft no, or refuse to accept it, or don’t see it for the gentle let down that it is. They only respond to direct, brutal honesty. You don’t want to be honest, and Karen doesn’t want to see your polite invitation declines as applying to the whole of your relationship.

Should you have broken up with her? Based on what ended up happening, yes, but how were you to know that going in? Turns out that Karen is deaf to soft nos and you were able to convince yourself each time that you turned her down that maybe, maybe, this time she wouldn’t text you again. Until she did.

What could you have said to have broken up with her? You could have said anything mean and true—“I can’t be around people who are so dismissive to the homeless,” or, “You hurt my feelings and I don’t want to hang out anymore,” or “CHECK YOUR PRIVILEGE AND I’M DONE.” But, based on what you’ve said about her so far, any of these could have easily become entrees into a dialogue about how you’re wrong to feel the way you do, or how she’s going to try better, which would just prolong a relationship that you’re trying to end. Friendships are like romances in that way: It takes two people to start it, but only one person to end it.

An effective break-up approach that ends things but allows the other person to think it’s all your fault would have been to make it all about you. “I’m sorry, but things are so crazy right now with work/a boyfriend/family/reality TV that I need to restrict my social life. Thanks for hanging out with me all those times, it was nice getting to know you, and I wish you all the best.” That’s not mean, and it’s direct, and it will likely result in the receiver losing your number.

But you went with the third option: being caught in a lie. My guess is that she hasn’t texted you since she caught you out when you claimed to be ill. In which case, that’s for the best. She’s done, she probably now thinks as little of you as you do of her, and the friendship is officially over.

Should you apologize to her now? If you were going to interact with her in the future—say, if you worked together, or associated with the same close-knit group of people who would be inviting you both to very intimate dinner parties, I’d say yes. But with your circumstance, don’t bother. You got the result you wanted, things are over, and you should keep them that way.

I know you feel bad about this. You’re telling yourself that she was new to the city too, she just wanted to meet someone to make her feel connected, she has so few friends, she was relying on you, you should have been nicer to her. Boo, please, stop. I think that she sounds like a big ass jerk and you had every right to get away from her as soon as you figured out that it was her world and you were just a sidekick. You don’t owe her your help, or your friendship, or your time. But it’s also good to remember that you also don’t really know her—she may have tons of friends you aren’t aware of. You weren’t her friend, and you also weren’t her savior.

Karen will go on overburdening people until she realizes that it’s a mistake—or, she’ll never stop. Either way, it’s not your concern. Learn from the experience. Note whatever warning signs she gave off at the beginning of your relationship and resolve to not engage with such a person again.

And then, most importantly, forgive yourself—it was a difficult situation, you tried your best to move away without hurting her feelings, and next time you’ll be sure that when you start a friendship it’ll be with someone that you actually, really, genuinely like.

Dana Norris once went on 71 internet dates, many of which you may read about here. She is the founder of Story Club and editor-in-chief of Story Club Magazine. She has been featured in McSweeney’s, Role Reboot, The Rumpus, and Tampa Review and she teaches at StoryStudio Chicago. You may find her on Twitter at @dananorris.

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