Devil’s advocate is a tricky rhetorical strategy. On the one hand, it can be extremely useful for exposing the flaws in an argument, helping others clarify and strengthen their positions, and practice your own argumentation. Using devil’s advocate when the topic under discussion is, say, whether or not we should pursue immortality or how best to end our dependence on non-renewable energy sources will probably be productive and enlightening.

On the other hand, when the topic is whether or not it should be legal to shoot unarmed Black teenagers or how best to respond to sexual assault, devil’s advocate is a minefield of potential faux pas, triggers, and discussions that end in yelling and/or blocking each other online.

Although some claim that in discussions like these we should be “objective” and not allow emotions to “get in the way,” I would argue that 1) it is virtually impossible to be objective about issues to which we have a personal connection, and 2) it’s not even desirable to be objective about issues to which we have a personal connection. For all their flaws, emotions alert us when the stakes are high, tip us off to our biases, and keep us fighting our battles. The important part is knowing what your bias is, and reminding yourself constantly to be on the lookout for information that doesn’t fit into that bias.

The reason this is relevant to the devil’s argument discussion is that people are going to have strong emotional responses to issues like sexual assault prevention. They just are. If you choose to play devil’s advocate during a discussion about an issue as personal and painful as this, you’re probably going to push some people’s buttons, and not in a good way. You’re going to sound exactly like the people who argue against them in earnest, and you’re going to make them defensive and cause them to double down even on parts of their arguments that are not that good. You’re going to jeopardize any chance of having a productive discussion.

Unless you learn how to be a responsible devil’s advocate.

First of all, and most importantly, accept that some people do not want to engage with devil’s advocates on certain issues. They do not want to hear about your thought experiments and hypotheticals. They do not want to argue with people whose positions on the issues are not clear, because it can be painful and even triggering to hear these opinions.

You may feel that these people are not doing their duty as Good Skeptics by not engaging in your Spirited Debate or supporting Free Inquiry or appreciating Diversity of Opinion, but it frankly doesn’t really matter. Some people don’t have the privilege to be able to look at issues like this objectively and without emotion because they have lived through the traumas and tragedies associated with these issues. If you can’t respect that and accept that not wanting to argue with you does not mean someone is Bad At Arguing or Bad At Skepticism, then you have no business trying to discuss these issues with anyone.

Second, make sure you have examined your own motivations for wanting to play devil’s advocate on an issue that’s personal and painful to many people. I’m not saying that there are no good motivations (insofar as you can discern “good” and “bad” motivations here); I’m just saying that it merits examination. Are you doing it to hash out your own doubts and figure out what you believe? That’s pretty legit. Are you doing it to help the other person argue better? Commendable, but not necessarily recommended; I’ll get to that in a bit. Are you doing it to get a reaction out of someone? If so, consider not doing that ever.

Often people are “rubbed the wrong way” by the discourse on issues like sexual assault, sexism, racism, and so on. They just find the claims made by progressives on these issues to be irritating somehow and they feel compelled to argue against them without really knowing for certain where they themselves stand or why they feel such a need to argue with a random internet person they don’t know.

A lot of the time, these people discover that their irritation and discomfort are stemming from unexamined prejudices, biases, and feelings of guilt. They realize that they’re actually worried that they will be perceived as an “-ist” or that they have undeserved privileges or that they have mistreated others because of bigotry or that they are resentful because they think minority groups are receiving special advantages of some sort. Examining carefully your reasons for wanting to play devil’s advocate can reveal some of these deep-seeded thoughts and feelings, and prevent others from using up valuable time and energy trying to get you to recognize them.

Third, if you’re playing devil’s advocate in order to try and help someone else, find out if that person actually wants or needs your help. Unsolicited advice is frankly annoying in almost any case, but especially when it involves a long, drawn-out debate with someone you believe to be in need of convincing, only to find out that they actually think they’re kindly bestowing their argumentative expertise on you.

If you’re not a progressive activist, you might not know how discussions generally work in our communities. We’re always hashing things out with each other, trying out new arguments, and asking for feedback. If we blog on networks or in groups of some sort, we often have private backchannels where we practice our arguments. You may think, running across a random blog or Twitter feed, that we’re desperately in need of someone to help us refine our views, but generally we have plenty of trusted friends and colleagues that we can do that with. So don’t assume.

Fourth, if you have now decided that you’re going to play devil’s advocate, tell the person what you’re doing. Be open. Get consent. Constructive debate is not that different from sex in this regard. For instance, here are some things you can say:

“I generally agree with you, but I’m having some doubts. Can I argue from the other side to see how you’d respond?”

“I’m not sure this argument will stand up to scrutiny. Do you mind if I try some counterarguments?”

“Want to practice debating this issue?”

“I don’t actually believe this, but just out of curiosity, how would you respond if I argued that ______?”

As Captain Awkward says, use your words. The clearer it is what you’re trying to accomplish and what your actual point is, the likelier it is that you’ll have a productive discussion and nobody’s feelings will be hurt.

And, as I mentioned in my first point, don’t forget to accept no for an answer. Do not respond passive-aggressively about how “sad” it is that you can’t even have a good debate about this issue. Do not snark at them about how “some skeptic you are.” Do not bloviate using grand, vague terms like “freedom of expression” and “free inquiry.” Do not pout about how you “just wanted a discussion.” If they say, “Sorry, this is too close to home,” say “Ok, sorry I bothered you!” and move on.

Fifth, be prepared for the possibility that people will misinterpret your arguments and positions as much more vile than you believe they actually are. You may be accused of rape apologia or various -isms or of not giving a fuck. Two things may be going on here: 1) the people you’re arguing with have a more accurate impression of your views than you think they do, because they’ve been down this road before; 2) the people you’re arguing with are extremely sensitized to horrendous bigotry and now sometimes see it in places where it isn’t really.

You may feel this is incredibly unfair, and that’s understandable. However, what’s considerably more unfair is how often these people, many of whom have been personally affected by the issues they’re discussing, have to deal with those who blame them and treat them like they’re subhuman and advocate for them to have their rights taken away (or not even given in the first place). Your arguments may sound exactly like the arguments made by those Actual Bigots, and so you get pegged for one.

Remember that being charitable means trying to understand why others often aren’t.

And remember that when it comes to social justice issues, the devil already has plenty of genuine advocates. There are people who tell us every day that bitches be lyin’. There are people who tell us every day that we shouldn’t ruin rapists’ lives by holding them accountable for what they did. There are people who say that Trayvon deserved it. There are people who say that a fetus has more rights than an adult human.

So, I will include the same cautionary note for devil’s advocate as I recently wrote for sarcasm: if you mimic terrible opinions and sound exactly like the people who hold those opinions earnestly, do not be surprised if people don’t take kindly to your arguments. Do not be surprised if we’re tired of responding to the same terrible opinion every day. Maybe you were bored at work and started reading a feminist blog for the first time in your life and wanted to play a fun game of devil’s advocate, but for those of us who write those blogs, that’s what we do every day. And for those of us who live the horrible reality of some of the issues we write about, facing the same terrible opinion for the millionth time can be too painful and stressful to be worth it.

You may be able to turn these issues into an engaging intellectual exercise while we may not. Do not hold yourself up as a paragon of emotional stability and argumentative prowess because of this. Understand that you’ve been lucky.

Update: added a link to this relevant post.