“This ‘Friendship’ Is Unbearable”
I met ”Diane” decades ago when she volunteered for a community organization I was associated with. After grad school, I ended up back in the same town to run the organization and she continued to be a huge supporter and volunteer….at a cost. While she is a well-meaning person, she is perhaps the most draining person I’ve ever encountered. She offers frequent unsolicited advice framed as “help” which comes off as condescending and judgmental (she ALWAYS knows the best way to do something regardless of whether she has all the information, relevant qualifications, or experience in a given situation). She holds people captive for 20- to 30-minute monologues about the most mundane details of her life, and she frequently pushes boundaries by trying to insert herself into situations where she has not been invited. Most recently, she has repeatedly “volunteered” to help me in my new business although I’ve never asked her to and have been very careful not to open that door for all the reasons above. Recently, I attempted to set much firmer boundaries, explaining that I won’t be asking her to help because I don’t believe in mixing business with existing friendships. She bulldozed right past that and provided a detailed list of things she could do to “help” me at my business anyway.
I am very sympathetic to the fact that she is a lonely person trying to make connections. She is in her mid-60s, has never married, and has recently been let go from a volunteer position because the issues above became untenable for another nonprofit director. It’s clear that she uses her volunteering as her primary social outlet, and her behavior is a major reason she doesn’t have close friends. Sadly, most people in our community find her unbearable as well. Just mention “Diane” and eyes will roll.
She thinks of us as close friends while I certainly do not, and while we share a long history, I find no joy in our relationship. Increasingly, I find myself getting enraged after every encounter with her, but I am unable to communicate it because of our long-standing relationship, my public-facing position, and, perhaps most importantly, my desire not to hurt her feelings. Instead, I hear myself venting about her to my friends, colleagues, and spouse, and I’m sure it’s exhausting for them.
Now that I have changed careers, I work in an environment where she can walk into my workplace at any time. When she does, I get hijacked for a relentless one-way recounting of the most minute details of her life. There is no reciprocity; she will talk about herself for 20-30 minutes and never even ask how I am. Worse yet, she has no respect for the fact that she does this at my place of work where I have 10 things pulling at me at all times.
I am genuinely worried that I’m going to explode at her one day and I desperately do not want that for either of us. In the past, I’ve tried to manage the strain of dealing with her by scheduling a lunch every few months so I could get the brunt of it out in one sitting, but now that I am more accessible in my new business, her appearances at work are much more frequent, and I have no desire to spend any additional social time with her. She, however, is pushing hard for us to spend time together. She doesn’t seem to be picking up on the fact that I’ve managed to put her off for almost eight months at this point.
We live in a small town and move in the same circles. I have a very close professional relationship with her sibling. Disappearing from her life is not really an option. I know I am not going to change her, but I don’t want to go another 10 or 20 years with this dynamic. If this were a romantic relationship, I would just break up. If this were a family member, I would offer some tough love. Is there a way I can reframe my thinking, or are there strategies I can employ to modify our relationship gently and kindly?
Many thanks for reading this and for your tough, clear-headed, direct advice. — Exhausted By Diane
Well, you’re right; you’re not going to change Diane. She is who she is and, truth be told, she’s probably going to become MORE of what you don’t like about her as she ages. But it’s not your obligation to put up with her unconditionally, and you can likely blame being socialized in a patriarchal society where women are encouraged to prioritize others for the feeling you have of being responsible for her. But you’re not responsible for her, and if you wouldn’t put up with a romantic partner or a family member behaving the way Diane does, then there’s no reason to accept the rude behavior of a longtime acquaintance/ neighbor/ community member (Diane is not a friend). You have to make your boundaries even clearer than you have, and doing so will mean accepting some discomfort in being the “bad guy”; there’s really no way around it.
So be the “bad guy” and tell Diane that, out of respect for your years of history together, you have to be honest with her and the truth is that with your new business you no longer have the time and attention for her that she’s used to. You have to tell her that she cannot come to your place of work anymore and expect your attention for more than a few minutes. You have to tell her that her presence and her demand of your time and attention are taking away from the many responsibilities you have and that you are beginning to resent her for it. I know this seems scary and maybe even impossible if you’ve never spoken to her or anyone else like this, and that’s OK. It’s not impossible. It may be awkward and you might feel bad for potentially hurting Diane’s feelings, but please consider this: Diane doesn’t care about YOUR feelings.
The thing with people like Diane is that they prey on people-pleasers because they know those are the folks who are most likely to put up with their shit. And you have. And this has enabled Diane to continue because she knows she can get what she wants – a captive audience – from you. The only way to stop this is to stop giving Diane what she wants. If you tell Diane she can’t keep dropping by your place of work and hanging out for 20 or 30 minutes and she tries to do it anyway, you have to ask her to leave. You have to say, “Diane, it’s great to see you, but as I’ve told you, I have a lot to do and I need to ask you to leave now so I can get back to it.” And just keep saying it. Keep saying it as long as it takes. If she asks if she can help you, say no. Say you’ve got it covered and the best way she can support you is by not taking up the time you’ve allotted to the work you have to do. It’s going to feel rude to you. Say it anyway. Stop enabling Diane to take advantage of you and she will stop taking advantage of you. It may not feel easy, but it really is that simple, and once you establish a new dynamic with her, you’ll wish you would have done so a long time ago.
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If you have a relationship/dating question I can help answer, you can send me your letters at [email protected].


We frequently think we have established boundaries when we haven’t set any at all. These people need the direct and firm approach.
May I offer one small reframe?
Diane doesn’t “prey” on the LW. Diane is just doing what the LW has encouraged and welcomed all these long years.
Inside of the LW’s mind, it’s very clear that Diane is unwelcome. To everyone else that the LW complains about Diane to, and in this letter, it’s very clear that Diane is unwelcome. But the LW has never been clear with Diane herself. With Diane, the LW has acted in a welcoming and encouraging fashion, pretending to be Diane’s friend while secretly hating her.
That’s a situation that cannot possibly be described as Diane “preying” on the LW.
Wendy, I hope you’ll learn more about neurodivergence before advising on situations like these in the future.
LW: what you described sounds like ASD or similar. Given her age and gender, she’s likely undiagnosed. Please do set limits on your time, but doing so with Wendy’s description that she’s “preying” on you will dispose you to being cruel. Diane sounds like someone who is working triple time to make connections, even taking on volunteer “jobs” to feel valued and connected. Yet it sounds like she has very few actual friends, everyone avoids and mocks her instead. I understand your frustration, but I hope viewing her behavior a bit differently will let you set boundaries with some compassion.
I totally agree with you.
How presumptuous of you. I’m very familiar with ASD. It’s not the LW’s obligation to coddle a woman who blows through the compassionate boundaries set in place. What you’re talking about is exactly what I mean about women being socialized to constantly prioritize the feelings of others to the detriment of their own well-being and we’re not doing that anymore.
Respectfully, you sound triggered by my suggestion to learn more about ND. Perhaps that’s why your reply sounds flippant.
In reminding you not to jump to broad, negative conclusions about a stranger who may be struggling…I’M the presumptuous one?
If you re read my comment, I simply suggested that the LW view this woman with compassion WHILE setting boundaries on their time. Framing “Diane” as a “predator” who “doesn’t care” about LW feelings, and making them put up with “her shit” predisposes LW to cruelty. Which is antithetical to setting kind, clear, firm boundaries.
I cannot force you to learn more about ASD, or the experience of older generations who were/are undiagnosed. But I will tell you that it can lead to excruciating social isolation and depression. Partly because they do not naturally pick up on social cues, and partly because of the uncharitable assumptions like those in your column.
And no, I’m not much older than you, if at all. I agree boundaries are essential. AND kindness costs nothing. Two things can be true at the same time.
Frankly, YOU are the one who sounds triggered. The advice I gave was from a compassionate place – both for the LW and for Diane. I’m not suggesting she be cruel to Diane. I advised she be clearer about her time restraints and to ask Diane to not come to her place of business for more than a few minutes since she has bulldozed past the LW’s previous attempts at setting clear boundaries. I think it’s weird that you continue suggesting that framing the situation as exactly what it is – one woman exploiting the long history of kindness, compassion, and patience by another woman who probably struggles with people-pleasing as cruel. I maintain that it is not the obligation of the LW to coddle a grown woman whom she has already tried to set clear boundaries with, and I think YOU lack compassion for a woman driven to her wits’ end by another woman with seemingly zero social graces at her place of business. Whether ND is the reason for the lack of social graces or not, the fact remains that this woman is robbing the LW of her time at work, her peace, her sanity.
Further, I DO think you are presumptuous – wildly so! (especially with the continued suggestion that I learn more about ND as if you have the faintest idea what my knowledge base is and what my personal history around ND may be). I also think you are wrong in this case to keep prioritizing the feelings of a woman who bulldozes past boundaries over a woman who has, so far, been nothing but patient and who, I surmised, needed some permission to prioritize her OWN feelings.
If you continue addressing me as you have been, I will block you. It’s one thing to disagree with or critique a person’s advice, but to express personal critiques and presumptions is a line I don’t tolerate.
I agree with you too.
I hope you can experience more time in the real world, she is absolutely preying on others.
As a recently late diagnosed person myself, this was my immediate first thought too!
OMG, I volunteered at a Hospital thrift shop and this exact thing happened to me. I thought people who volunteered were kind hearted people that wanted to help. But I ran into a few people that were just doing it for the perks of discounts etc. I also got stuck with a “Diane” and all she did was talk about herself for the entire shift. She would repeat the same stories and complain about the same stuff over and over again. I finally quit. I just could not take it anymore. She was not neuro-divergent. I didn’t have the heart to say anything to the manager it felt wrong.
You can be honest with her and maybe offend her. But maybe this is what she needs. Thank you for the offer of help Diane, but we have people with more experience/know how in charge of getting that stuff done.
Just straight up say. I’m sorry Diane your long visits are taking too much time out of my day. I really need to ask you not to come visit me at work. If you would like to chat sometime send me an email and I’ll see when a good time to get together is and never find a good time. But honestly, it doesn’t sound like Diane is good at taking subtle cues so I think the firm straight forward approach is your only hope.
If you are friends with her sister can’t Diane’s sister have a talk with Diane about her issues?
I agree life is too short. I have a rule about cutting parasitic people out of my lives. They suck the life force from you. It’s hard to tell if Diane is just a sad lonely soul or a narcissist. But either way it’s time for you to draw some boundaries for yourself.
Reading your post, one wonders why it is so difficult to say to someone like Diane: “Sorry, I can’t talk to you, I am working and busy, I am afraid you have to leave now.” If she insist: “Please, let me work, I can’t socialise while working, I must deliver. Please respect my professional duties”. And you stand up and accompany her to the door. I would also stop the lunch meetings as it sends mixed messages. Either you enjoy talking to her, or you don’t: don’t be ambiguous. I don’t like either that you “complain” about her all the time to everybody: that’s mean and also pathetic. What you are saying is that you are unable to set normal boundaries. Who would let anyone paralyse them during 20 minutes by a monologue while they are working? Have more respect for your own job and just be clear with Diane. You can walk her to the door without being hard or offensive: you are just busy and have no time.