Friendship dilemma: What to do?
January 6, 2011 4:55 PM   Subscribe

I need advice about a friendship

tl;dr: My best friend, Lily, has been having a really rough year - due to several things, but most importantly, her 3-year-old daughter getting diagnosed with leukemia. Lily and I are also business partners. I feel like our friendship and partnership have taken some major hits over the year, and I don't know what I should be doing at this point.

longer version - sorry for the length:

Four years ago I started an IT-related business with a friend of mine. At the time, she was a reasonably good friend from college, good enough to have stayed in touch with - we are now in our mid-thirties - and to respect each other a great deal but not best friends or anything. Over the course of the next four years, we grew really close - were maid of honor in each others' weddings, our families regularly spent weekends together, etc. All in all I would have said she was my closest friend in many ways.

A year ago her youngest daughter was diagnosed with leukemia. As you might expect, this has, naturally, been horrifyingly stressful for their entire family. I've tried to do what I can to help: offering to babysit one or both kids, taking up slack at work, and just being there to talk to, mainly. Unfortunately, since work is a jointly-owned business, even with me taking up some slack, work was still really busy for Lily - I could only do so much, and I think to some extent she liked having it as an escape.

Mainly because she was trying to be strong for her family, I ended up often being the person that she confided a lot of her fears and worries to. I was happy to do this but I think this resulted in a strain on her relationship with her partner, Kate. Whether because of this or other reasons, I don't know, but starting in August I feel like Lily has really pulled back from me. I know she had some sort of fight with Kate, and after that she told me "we can't hang out as much anymore" - but in addition to spending much less time with me than she ever did, she's pulled back emotionally a lot as well, even while trying to maintain a charade of "still friends". And now I veer wildly back and forth between trying to give her space and do what she plainly thinks she needs to do for her family and her relationship, feeling really resentful at being "dumped" while still continuing to take up the slack at work - and having to do so for the indefinite future -, trying to stay professional for the sake of the business, and just plain missing my best friend.

Part of me, the human part I guess, is really upset, and I find myself having to battle back growing mounds of resentment whenever I interact with her. She hasn't ever dropped the ball in a major way at work, but I do increasing amounts of the day-to-day crap: employee meetings, administrative blather, etc. And I feel like I've been doing it so long - for a year or so now - that it's become normalized that I'm the person that does it. Whenever I find myself doing it I have to actively work not to get upset about having to do so. (This isn't something we can offload to someone else, either - it has to be one of us). Sometimes she'll have an idea about things we can do to improve the business or the product, and my immediate bitter instinct is to shoot it down because I know I'll end up having to do most of the crap involved in getting it off the ground.

The thing is, all of this work stuff bothered me a lot less when she was still being my friend and confiding in me - so I know probably a lot of my feelings come from resentment and hurt over the friendship. I'm really hurt and I really miss her. I feel stupid and drama-queeny to feel this way, because she's been going through so much and to some extent I can tell she's trying to maintain some element of friendship - occasionally (like, once or twice since August) she'll drink a few glasses of wine and open up and it feels like it used to. And because we work together, we still see each other all the time - even if, by her preference, we almost always talk about work; I used to try to turn the topic towards more personal things, and she'd always deflect it quickly back to work, and I've stopped trying so much - it's too painful, and it also feels disrespectful of her clear choice. So it's not like there's nothing left, but I still feel largely cut out of her emotional life. I can't bring up the topic and talk to her about this, because it too gets deflected quickly. I also don't feel like I can rely on her for talking about any of my problems, even though they seem rather trivial in comparison to hers.

So that's how I feel. Yet a large part of me thinks I am an awful person for feeling this way, and I should be more understanding. I can't bring myself to really blame her - she's been dealt a shitty situation and she's dealing with it the best way she knows. If it really is the case that she or Kate felt that her relying on me and spending time with me was getting in the way of their relationship, then that relationship has to take precedence. And I certainly can't blame her for feeling so incredibly stressed and trying to be so many things to so many people that she had to drop a few. I mean, if I was triaging and I had to choose between my best friend and my family - including my very sick daughter - I'd choose the same way.

I recognize all of that intellectually, but I still feel hurt and resentful.

My question: What do I do: how do I be fair to Lily, and how do I take care of myself at the same time? So far I have just tried to keep it professional and have almost entirely ceased to push at the friendship, aside from trying to maintain occasional lunches - which almost always end up being about work, but it's still something. But I'm only feeling more and more resentful and hurt. On the other hand, I don't think that pushing her on any of this will help either: I think I know what's going on, I can't even fully disagree with her decisions, and it will just cause a fight and add another load of stress to both of our lives. My goal, at the very least, is to maintain our professional relationship for the sake of our business, which was a dream of both of ours and is still a source of a tremendous amount of satisfaction for me. I also want to do what I can to support Lily and her family - her daughter is in partial remission but the long-term prospects may not be great, so this year might even be worse than last year was. But I don't want to be a pushover, and I want to somehow deal with the resentment and hurt I feel in such a way as to minimize the collateral damage. I'm afraid if I don't, it will build up and I'll explode and ruin everything we still have. I've tried to spend more time with my husband and find new friends and hobbies, but work is so consuming that I really can't dedicate enough time to them to get much in return (aside from my husband, that is; he has really been my rock throughout this whole thing). I just don't know what to do - how I can act with dignity and integrity, while not being taken advantage of or being a bad friend?
posted by fluffysocksarenice to Human Relations (18 answers total) 2 users marked this as a favorite
Talk to Kate. Find out what is going on.
posted by Ironmouth at 5:03 PM on January 6, 2011 [1 favorite]

Don't feel shitty or drama-queeny -- you've handled this So Much Better than most friends or business partners would, let along both. You have every right to be hurt, and don't tell yourself anything else. It hurts any time anyone does something that feels like rejection, even when we know all of the really good reasons they're doing what they're doing.

You're on the right track, friendshipwise, in relying more on your husband and other friends. As much as it sucks, that sounds like the best you can do there. Which really sucks, because you've basically lost your best friend by doing nothing wrong - by doing everything Right, friendshipwise. So again, give yourself permission to feel the anger. Just because she didn't have any good choices doesn't mean she hasn't still been a bad friend to you.

Business-wise, though, you need a release valve. Maybe sit down with her at lunch and brainstorm with her about how to relieve some of the pressure on you? Do you guys hire someone to do more of the admin stuff, can she step it up, put off some of her ideas, etc? Maybe it should be in the context of looking at what you're both doing now and where the business is headed? It sounds like this is the sort of problem she can work on together with you, hopefully.

Good on you for wanting to continue to be a good friend to her and her daughter, and I hope you guys can be good friends again some day. But for now, take care of yourself - you need it, too!
posted by ldthomps at 5:28 PM on January 6, 2011

I would talk to Lily. I think going to Kate would be a bit of an overstep.

I think the resentment over work is simply a side-effect of your hurt feelings about the friendship. My sense is that once those emotions get resolved, the resentment will resolve itself as well.

You say in very general terms that the closeness of your relationship was bothering Kate in some way, and they decided as a couple that Lily needed to step back from the friendship. Were you ever given a clear explanation of what was happening beyond "I need to step back from our friendship - Kate feels that it is interfering with our relationship?" It sounds like you are genuinely sympathetic and trying not to take this step back personally. To me that indicates that you weren't given much of an explanation and there are some lingering questions that have allowed doubt to creep in. Otherwise, you'd likely miss her but I think you'd have an easier time processing the changes. You'd know that it wasn't personal and the difference is helping your friend through a difficult time.

The other explanation is there is more to the story and your friend has used her partner as an excuse to avoid facing it. The point is, you won't know until you ask.

I'd ask Lily to lunch and have a check in. Find out how she's been and let her know a bit about what you're feeling. There is a middle ground between an overly intimate friendship and a near complete cessation of contact. Timing might not be great, but the alternative is worse - you don't want to let your emotions go unchecked for so long that the relationship is no longer repairable and it affects your work.

It is in her best interests that you maintain the pieces of her work that you've taken on while she deals with her family. Make it clear that you are coming to her only to understand and possibly renegotiate how you interact so you can feel comfortable in your friendship without encroaching on her relationship with Kate. I'd also let her know that you exhausted every possible method of addressing the situation before involving her so as to not burden her with your emotions but found no other way to address it and are worried that it is affecting your ability to help her at the office. If you are as close as you seem to be, I think it will be a positive conversation for both of you.
posted by amycup at 5:35 PM on January 6, 2011

Response by poster: amyms- I was never given a clear explanation. All I knew is that they were having "some trouble" in their relationship - even before August, Lily didn't like to go into details about her relationship with Kate - nor I with my husband, we're both pretty private about that sort of thing. Then one day she and Kate had some minor fight over a trivial thing and when Lily left work that day she said she "had to have a long discussion" with Kate about everything that evening. The next day she told me she couldn't spend as much time with me. We didn't discuss it much at the time - it was a very busy day - and I thought I understood and I'd get the full story later. She said nothing about also stepping back emotionally or anything, and needless to say I haven't gotten much of the story - or any story - since. Everything else is just my attempt to reconstruct what happened.

So you're probably right that never having really talked about this is part of what makes me feel bad. But I don't really see how to sit down and talk about it: Lily just won't let me broach personal topics, and is a master of deflection - to the point that I feel like forcing her to have this conversation would be almost as damaging as me letting my resentment build to the point that I explode at her.

Thanks to everyone for the thoughts. It's really really helpful, please keep them coming.
posted by fluffysocksarenice at 6:13 PM on January 6, 2011

It sounds to me like you've been an exemplary human being through all of this. So first, cut yourself some slack for feeling the way you are; it's only natural.

Next, I think that given your necessary professional relationship, you're going to have to mourn the reduced intimacy in your personal relationship and move on, at least for now. It sounds very much like a situation where doing anything beyond accepting the new status quo is asking for trouble.

At the same time, you shouldn't be the one pulling all the weight of the company. I agree with idthomps that you should have a meeting and try to come up with ways to lighten the load on you.

And... I'm sorry you've been going through this. It sounds really rough, and again, it seems like you've dealt with it as gracefully as possible.
posted by Andrhia at 6:16 PM on January 6, 2011

I think this may be one of those times where a letter might be effective. It gives you time to carefully state what you want to, and does not pressure the person to respond (or deflect) on the spot. Using "I" statements to express your sadness and confusion, without demanding answers, may help you feel better for having expressed yourself, and help her to see that you are struggling. Give it to her without much expectation of resolution, at least right away. I empathize with you--this seems like a very painful situation.
posted by thebrokedown at 6:48 PM on January 6, 2011

Is it possible she was falling in love with you, or at least thought she was? That would explain why she couldn't tell you what the issue was. It would explain why her partner doesn't want you to have so much contact and it would explain the severe back-off.
posted by InkaLomax at 6:59 PM on January 6, 2011

Response by poster: InkaLomax: I think it's possible, but unlikely. Possible because we were really close, and I am the gender she's attracted to. Unlikely because we had years of close friendship without any indication I was aware of that she might feel that way to any notable degree - I can be oblivious but I would hope not that oblivious. Nevertheless, yeah, the possibility had even occurred to me - indeed, that possibility, however remote, is one reason I am not sure that forcing a conversation would be a good thing. I don't think the situation would be helped by her confessing something of that nature - it might just make things even more awkward and fraught.

That said, I think it's more likely that Kate simply thought Lily might be falling for me, even if Lily really wasn't.

Or, really, most likely of all to me is just that she - or they - mutually thought that our emotional closeness was getting in the way of theirs, especially given the strain on their relationship caused by their daughter's illness.

Sorry, I'll stop thread-sitting now.
posted by fluffysocksarenice at 7:24 PM on January 6, 2011

You know what? I don't think this is about personal stuff, and I think you are being WAY too hard on yourself in that department. I think this is about Business!

Inside all of the stuff you are second guessing, you admit that you've taken on heaps more of the business side of things to give Lily some breathing room, and that this increase in your workload has become permanent. THAT'S HUGE. The fact is, you are no longer working together in the same manner or in the same ratio as before. You came to share as much with Lily as you did primarily because of the business relationship. Now that business relationship has changed, and you are getting less on all counts.

That's not fair of Lily. She's not being a good business partner to you.

I think you are pointing at the friendship issues because you believe that to point at the business issues, especially in light of her daughter's illness, would make you a Bad Person. Don't fall for it.

And you know what else? Because you were on such friendly terms, that made working together way more fun - right? Now that it's all changed, from your workload to your feelings about working with Lily, no wonder you are feeling badly.


The above was a long way of saying that Lily's external life has altered your working partnership. Since things will never go back to the way they were when you started out, I think you should start focusing on how to get the passion and enjoyment back into your daily work experience - and this might include changing Lily's partnership level to reflect her contribution. If things were more fair in the work department, this change in the personal relationship would have been a breeze for you to roll with.


I don't know what Lily's partner Kate was on a bout, and as understandable as some folks think that aspect of the situation is... Yuck. Sorry you got caught up in that. Truly.


Go fix the business side of this. It's the one aspect you have control over, and fixing it to support your peace and happiness will net you the best return on the investment you make daily in your company.

Good luck.
posted by jbenben at 7:31 PM on January 6, 2011 [2 favorites]

I can't bring up the topic and talk to her about this, because it too gets deflected quickly.

Yeah. Throughout your question, I thought, "okay, you guys need to talk about how abandoned you feel." Then I got to this. Ugh. If you really can't have her at least acknowledge that she disappeared on you, then you can't really have a mutually supportive and honest relationship anymore. My first response was that friendship breakups are just like real breakups, where sometimes you need a clean break. But it sounds like you can't just sell the company or take a sabbatical.

Since you can't really have a dialogue about the situation as friends, could you at least have it as business partners? I'm not sure how far you can get, because I'm not sure how checked-out she is overall and how sanitized the conversations are. Ideally, you'd feel like your pain was heard and acknowledged, even if she couldn't change its cause. But at minimum, you can negotiate changes to your business relationship that will make the situation more sustainable for you.

One option would be to explain your human emotions, then shift the conversation onto safer business terrain where you can together take the emotional subtext as a fact, and as business partners, decide how to make the work situation more sustainable for you both (the same as if a staffer were to say "my mom is dying and I'm incredibly sad. Can we find a way for me to take additional time off this month?"). One potential script is below, though it might be too much for your relationship now.

At a minimum, I'd decide, in business terms, what needs to change to make this emotionally sustainable for you. Can you identify how these emotional challenges could be met by a shift in your business relationship? I'm assuming that resentment is the main one, stemming from inequity and from feeling unappreciated (things could be made more equitable, or at minimum, your greater contributions could be acknowledged and appreciated, perhaps even rewarded monetarily), a secondary one is loneliness (you could cut back on overtime to have more non-work time to develop new friendships), and a third possibility is just plain hurt and rejection (you could find ways to work separately for awhile).

One potential script: "Lily, can we talk briefly before you head out? Do you have a few minutes? [pause] I need to talk to you about something going on in my personal life that's starting to affect my work. Two things actually. One is that I really miss the way our friendship used to be. I'm not asking you to change or blaming you; I respect that you're doing what you need to do for your family. I just wanted to tell you that losing the way our friendship used to be has been hard on me. I've sometimes felt sad, abandoned, or lonely. Mostly, I just miss our fun. Again, I'm not asking you to change -- I feel better just saying this and having things out in open. The second thing is that here at work, I've begun to feel resentful about picking up some of the slack. I know how hard things have been with [Child], and I didn't mind doing extra before, but in the wake of losing our old friendship, it has been harder in several ways. I still really value our business partnership and look forward to staying in business together for a long time. And I want you to be able to meet your family obligations and do what you need to do during this difficult time. But for myself, I'd like to put in less overtime so I have time to develop other strong friendships; I'd like to put in more equitable amounts of time and effort; and when I do have to put in more time than you, which I understand will occasionally happen, I'd like to feel like that extra work is being seen, valued, and maybe even rewarded. Let's discuss what it would take to reduce the business demands on you and me to a level that is tolerable and sustainable for each of us, and how to create a sense of equity and balance on occasions when I need to put in extra hours. I'm sure we can figure this out. Let's think about it over the next couple of weeks as we do the budgets. Anyway, thanks. You're an amazing scientist and businesswoman, and I am glad to work with you. I am so proud of what we've done here at Business, and I don't want all of this stuff to get in the way, I want to find a solution that works for us both over the long run. So that we can kick [competitor's] ass! :)"
posted by salvia at 9:26 PM on January 6, 2011 [2 favorites]

Whoever you do talk to, have what you want to say rehearsed. Let your husband "play" the other person so you won't get deflected.
posted by Ironmouth at 10:06 PM on January 6, 2011

Now is not the time.

Lily has a sick kid and a rocky relationship with her partner. (Couples often struggle when a child has a long term illness.) Lily's barely keeping it together. Adding one more person's needs is pushing her pretty close to the breaking point. Under that amount of strain, she's as likely to snap at you as she is to simply collapse. You've been an awesome friend during a difficult time and it's okay if you need to pull back your friendship now.

Instead, get your business life in order. Tell her you need help and your going to hire someone to assist you. That's totally fair.

When her child's illness stabilizes, perhaps you can resume your friendship. Maybe you won't want to do that.
posted by 26.2 at 10:23 PM on January 6, 2011 [6 favorites]

For any number of reasons, I'd set aside the friendship conversation (friendships evolve, have phases, fade away, etc., for all sorts of reasons) and focus on the operational stuff that will ultimately have the biggest impact on your life: the business. Linking the two in a Big Talk sounds too likely to get tangled (in emotions).

Not clear from your words about how much the daughter's illness is placing demands on her time and energy, but it sounds like you're reasonable in your expectations, displeasure with taking on more and more work... and she may well be reasonable in the daughter's condition taking a significant toll on what she can give.

As ever with work things, the old line, "Don't bring me problems, bring me solutions to problems," so maybe you can relate some ideas, specific things you need help with, etc.?
posted by ambient2 at 10:29 PM on January 6, 2011 [2 favorites]

It sounds to me like you've been a great friend in need and you should take pride in that.

Maybe this is what Lily needs most right now: someone she can be all business with, so she can spend her working day shutting out her fear of what might happen to her child. Or perhaps the things she's struggling with aren't easy or comfortable to share with someone who hasn't experienced anything like that, no matter how sympathetic you are. Or she could just have very limited energy for maintaining close relationships, and Kate could have felt left out when a large chunk of it was spent with you. There is a possibility Lily was even having an escapist crush on you - people under a great deal of stress can be prone to that - and needed to step back. Or she could've simply felt guilty for burdening you with the extra workload and her feelings. Or maybe she can't deal with your need for friendly intimacy when her own life is as demanding and scary as it is right now. And I mean this in the kindest possible way, but perhaps she doesn't want to hear about your problems because she knows you're a good person and deserve a friendly shoulder as much as anyone, but all she could think of was "my child could die and my relationship is crumbling and you're whining about X and Y".

In short, we can't really tell - and apparently, neither can you - and personally, I'm of the opinion that perhaps in this case you should just try to accept her choice for now and not even ask for an explanation. (If she were irritable or hostile, it would be a different matter.) If you can, give her the space she seems to want now and find ways to deal with the practical, work-related issues separately. Friendships ebb and flow - keep reminding yourself that there's a very good possibility yours will bounce back in time. Do you have other friends you could spend time with, or old friendships you could try to rekindle in the meantime?
posted by sively at 2:04 AM on January 7, 2011

Lessons imparted from the book Difficult Conversations really helped me understand how to deal with situations very much like the one you describe. It's especially cloudy because you have a business and friendship relationship melded into one, and the archetype of how you might want to behave in each of those steps on the other's toes.

I would offer that until you get some explanation of the rest of the story about Lily pulling back, your business relationship is going to be strained. It's the emotional content of the problem that makes it difficult; otherwise it would be easy.

Best of luck.
posted by desl at 8:17 AM on January 7, 2011

She's being pulled three different ways by some major things in her life and your friendship was the thing that had to give.

First there was her daughter's cancer. This undoubtedly placed an enormous stress on all parts of her life. She coped with this partially by leaning more heavily on your friendship and retreating into work. This led to problem #2, which is that it sounds like her wife accused her of having an affair with you or wanting to. (Based on the fact that they fought and the wife asked her to cut you out, this seems like a reasonable conjecture.) Picture if she was a guy and your husband were the type to be jealous. Would he have had twinges of unease at how close you were to your "work spouse"?

So she has two unbearable possibilities: that she'll lose her daughter or that she'll lose her wife. The third vector was your friendship, and because she couldn't afford to lose either of the other two things your friendship was the one that had to give. (Not that anything she is able to do will have an effect on whether her daughter's cancer recurs, but in the emotional calculus of daughter vs friendship, daughter will win every time.)

So I think you need to come to terms with the fact that friendship-wise the choice she made to spend less time with you was the only choice she felt she had. This should be treated as a separate issue from the business. I think as far as the friendship goes, the most you should say is something like, "I miss spending time with you, and I know how hard things are right now, so I just want to let you know that if you ever need me, I'm here."

When it comes to the business, you need to have a longer, and separate, conversation, where you talk about the unequal division of work and what can be done to re-balance it, or shift some to others.
posted by MsMolly at 8:48 AM on January 7, 2011

If you really can't bring yourself to talk to her about this, can you write her a letter and give it to her one day when she's leaving work? Be gentle in the letter as she's going through so much, but just tell her you miss being close to her, and also that you're feeling overburdened at work and would like to have her ideas on how that could be fixed. Hopefully she'll suggest either dropping some of the workload entirely, her stepping up to the plate in certain areas, or hiring an assistant. Think about it beforehand to figure out what would be acceptable to you so you can have a productive conversation.
posted by hazyjane at 10:02 AM on January 7, 2011

Response by poster: I appreciate all of these answers, and don't really want to choose a "best" one because they have all led to me thinking about this in a useful way.

It sounds like the most appropriate thing to do will be to talk to Lily calmly about the business side of things - at the very least, even if not much can be done about our unequal workloads, I might feel more appreciated by her for it - and it's acknowledged that this isn't a permanent state - then I can get rid of some of my resentment about that. And maybe she will have some ideas for how to take some of the load off of me while not overburdening her. If I don't have that daily source of frustration and resentment, it might ease the ongoing resentment and hurt substantially.

As for the friendship end, it does sound like I just have to live with it - which is sort of what I've been thinking. Typing all of this out and getting your feedback has been very helpful for those feelings, actually - just communicating about it and being heard, even if not by her, has been really nice. Thank you especially for the sympathy and validation. For that reason I like the idea of writing a letter about my feelings, which I think I'll do when my hurt starts building up - but I won't ever send that letter, I'll keep it to myself, or just show my husband.

Maybe in time our friendship will recover. Maybe it won't, which is horribly sad - she really was one of my best friends ever, and I had seen our friendship lasting a lifetime - but I can't really fault her choices here; as many of you point out, she has probably done what she had to do. In the meantime I'll just try to act as well as I can from my end - which includes still babysitting her kids and doing what I can to help the family out in the upcoming year - so that if the friendship does die completely, it's not because of behavior I need to be ashamed of on my part. It is just life. Thank you again.
posted by fluffysocksarenice at 3:14 PM on January 7, 2011 [1 favorite]

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