1) You’re asking someone to feel exactly how you feel; to have the same emotions, the same perspective, and then agree with you. If they don’t concur (and they probably won’t) you end up in a circular debate in which the other person finds new ways to discount your feelings. Replies such as, “Well, I would know that it was just a joke and I wouldn’t be such a baby about it!” or “I wouldn’t care so neither should you” most certainly won’t bring the two of you any closer to resolving the issue.
2) You’re asking someone to read your mind, to know the impact of every action that’s ever happened to you, and then know how that historical impact is being applied to the current situation. They can’t do that–only you can. Asking the other person to make the leap from “You wouldn’t like it if I took you to my company picnic and left you to fend for yourself” to understanding the issues you have with unpopular memories from high school is unreasonable if you haven’t explained yourself. People really don’t just know things; we have to tell them.
3) The question muddies up the conversation because the two of you start debating whether or not the statement is true. Responses that include odd and old examples like “that one time when you did that thing that’s sort of like the thing we’re talking about now and I was okay with it” only cause huge distractions and completely derail the discussion.
When “how would you feel” questions are inserted into a debate, the best one can hope for is a response with some level of understanding. And, that happens sometimes. But then what? It may seem you’ve gotten through to the other person but keep in mind that there can’t be that much understanding taking place because you haven’t spent any time discussing what the action brings up for you-i.e. the real issue. Rather than continue down the path of assuming synchronicity I think it’s beneficial to stop and reconsider whether the point is to get the listener to agree with you that they would feel exactly the way you feel or if the point is to gain understanding based on something deeper. I vote for gaining understanding based on something deeper.
When I’m the person ready to blurt out “how would you feel if…” I stop myself and reconsider. I take a moment (okay, sometimes I take days) to figure out what the real issue is for me. Then I own it. I will re-enter the conversation by admitting that what I have to say may make no sense at all to the listener but it’s how I feel and it explains why I’m having such an emotional reaction. I talk about what the situation brings up for me and I let go of the need to have the other person say she’d feel the same way in my shoes. Rather, I explain myself and ask if she will agree to do or not do xyz in the future now that I’ve shared with her where I’m coming from and, more importantly, why. Oh, and I make sure to include a discussion about what the issue brings up for her as well.
If I’m mediating and one of the parties starts in with a “how would feel if…” question, I help both parties through the same process I use for myself. I acknowledge the question by asking what the issue brings up for both them. Though it may seem obvious to focus only on the speaker, I know that there is also something at play for the listener. Perhaps she has no experience with the issues the speaker is bringing up or perhaps she’s applying her own historical event to today’s issue. The two don’t need to agree on how one should feel about the issue; they simply need to spend some time listening to each other’s expanded perspective on it.
Providing clear explanations about how and why an action affects you (or not) is a great way to set boundaries around possible solutions and agreements. Not understanding why one shouldn’t leave her partner alone at the company picnic makes it easier to come up with ideas on how to ease his anxiety with your co-workers than it is to smother him with embarrassing attention at the next event. If she knows how mingling with others without her makes you feel, she’s more apt to honor your request to stay nearby (or take the trash out without being asked, or pick up the kids from daycare on time, or refrain from rolling ones eyes behind your mother’s back, or…).