Should you point out a friend's flaws when they ask for insight into problems with another relationship?

Question

This has happened to me more than once.

I have a friend Sally who has annoyed me for certain reasons. One day, Sally tells me that it seems like Jane has been annoyed with her but she does not know why. When she explains what has been going on, it seems to me like Jane could be annoyed by the exact same things that I find annoying/off-putting about Sally. I don't know Jane, so I can't say for sure.

How do I tell Sally that perhaps those things which annoy me (I've never told her that they annoy me) are what's annoying Jane? Would I only mention them in the context of the situation with Jane, or do I also mention my personal experiences/grievances with Sally?

If it matters, in one instance Sally was extremely confused about what would cause Jane to distance herself from Sally. She brainstormed a list of possible reasons but came up with counterarguments for each one to make them sound farfetched. One or more of the items in her list are indeed things that bother me about Sally.

For example, a reason Sally came up with: Perhaps Jane thinks I am trying to mooch off of her.
Sally's counter-argument: But I offered to pay.
My view: Sally is one the biggest moochers I know.
Both from my experience and from the story she told me about Jane, the rare times that Sally does offer to pay are inappropriate. For example, she may offer $5 for a half mile ride to her house. While tempting to accept because she rarely offers up anything on her side, I would not feel right accepting money for such a short ride.

How could I tactfully react?

Answer 1

The best answer is going to depend on Sally's personality and motivations. For this answer, I'm going to assume she's generally sensitive to criticism, but I'm a stranger on the internet and potentially dead wrong.

One possible motivation is that she merely wants sympathy for this bad thing that's happening to her. The list and counter-arguments make me especially believe this is the case, as she's already discounting the premise that she did something "bad."

In this instance, if you're all right tolerating your personal irks with her, then just be a friend. Listen to her complaints, acknowledge she has good reasons to feel how she does, and move on.

If you believe she wants an answer, or you're bothered by her quirks and want to use this as a chance to speak up, however, then a soft approach would be best for someone sensitive to criticism.

Discuss her list of possible reasons, only now come up with counter-arguments for her counter-arguments. You want to phrase these in the manner of, "Is it possible that (Jane/people) ..." rather than the "Well, actually" approach. The latter seems matter-of-fact and argumentative; you aren't trying to strike a debate about Sally's qualities nor rub her nose in being wrong, your goal is to get her to acknowledge that people will feel and think differently than how she expects them to.

As a specific and contrived example, one of her counter-arguments may have been something like, "but Jane would have told me that X was the problem." Your counter-argument here could be something like, "It's possible that Jane wanted to, but never found the right time."

This is where my answer breaks down, as there are many follow-ups from here.

If you want to be more blunt about your grievances, you can use "I" examples instead of abstract "Is it possible..." ones. Eg, "I know I didn't tell you X was the problem, because Y." Pros: Voicing your opinion, becoming "the honest friend," and more likely to see results for your issues. Cons: Feelings may be hurt and you almost need to sidetrack and now have a conversation about you and Sally, returning to Sally and Jane later.

If you want to be more subtle, but maybe still see change, get her to think about these counter-arguments on her own. EG, following up our example with something like, "Can you think of any reasons Jane wouldn't tell you about X?" Try to direct her towards the reasons that apply to you. Pros: Self-sufficiency, saving face, less likely to end in hurt feelings. Cons: Your specific grievances will only change by coincidence, and maybe not at all.

Either way, Sally should talk to Jane to sort this out. Remind her to be open, try to understand Jane's feelings, avoid arguing, and perhaps with her new list of plausible complaints, ask Jane if it's one of those/what she can do better about it.

At the end of the day, how much you interject your feelings is going to depend on the response you want. Hopefully I've laid out enough situations to help you pick a direction.

Answer 2

Two approaches

1 Drop it on Jane

If you don't want to expand this into a question of you and Sally as well, go here. Tell Sally that she should talk to Jane, say "Hey Jane, have I hurt your feelings lately? You've seemed distant." If Sally really wants to keep Jane's friendship, she needs to reach out and find out what the real problem is. It might not be the same thing that bugs you, after all.

2 Tell her

You don't know much about Jane, so your own read on Sally and frustrations with her are what you have to go on. You can speculate with her, but you'll end up having a conversation like this:

Sally: What could it be?

You: I can only guess. You need to be absolutely rigorous in splitting costs with her.

Sally: [the dawn rises slowly] Wait ... do you think I'm a mooch?

You: Um, er, ahem ahem.

Point being ... she's basically grabbing you by the lapels and asking "What are my character flaws?" That conversation rarely goes well.

Also, just like above section, she needs to talk to Jane anyway.

Recommendation

Look, Sally is upset and asking you for help. If you have your own problems with her, you've had plenty of time in the past to bring them up, but haven't, for your own reasons.

Sally is worried about her friendship with Jane. Focus on that. The whole "I think you're a mooch too" bit can wait. Go with option 1, let the poor girl deal with one crisis at a time.

Answer 3

No, unless you're already famous for incisive candor, (or tolerated in spite of it), responding to that friend's grievances by sharing theories about your friend's flaws as hypothetical causes of unknown third party breaches would be unpleasant. What's wanted is a pep talk, in which one may remind and commend the grieved party for those qualities they do have, not hint obliquely at the many things you believe they lack. Your friend just wants a sympathetic ear.

Also, without knowing the third party, how do you know they aren't themselves at fault, or weren't having a terrible day, etc. Give a friend the benefit of the doubt.

Put another way, commiserating with a friend is a bit like hiring a defense attorney, and nobody wants their defense attorney to turn into a second prosecutor. Their accuser (Jane) has probably already been on the job of finding and hinting at faults, so any efforts there might be redundant. Your sketch of Sally makes it sound like she already knows her own faults and is hoping for reassurance that you wouldn't drop her for the same reasons Jane may have.