I would reconcile yourself to the fact that you're going to crack a few eggs in the process of making this omelette.
Although — better fewer but better, as a wise man once said.
I would pick your battles, given that you are in a position to do you. You might be surprised at how far you can shift individual's perspectives if you take a gradual approach; it's very easy to denounce someone and cut them out of your life but, unless it's because you find their behaviour reprehensible, that generally only makes people more entrenched in their position. Sometimes allyship means being behind enemy lines and doing the hard work that the groups who you are an ally to are unable to, whether due to the fact that they aren't welcomed into the Old Boy's Club or due to the fact that they have to prioritise their own family/community/mental health.
In these situations I find that I am constantly engaging in a degree of calculus: how much goodwill and trust I have with this person, how much goodwill will be eroded by challenging them, how high a priority any particular issue is to push back on... basically it's weighing up how much far I am able to stretch the relationship without it snapping and how important it is to leverage the relationship for driving critical consciousness.
What that means is that I do not swing at every ball. Sometimes I let smaller shit slide in order to tackle the bigger issues. It sucks to have to compromise but this is the nature of doing hard work in the community and agitating for change. Sometimes I don't tackle that bigger issue head-on but I choose to voice dissent or to point out a pointed semi-rhetorical question before moving the conversation on.
[CW for mostly abstract discussions of everything awful - queerphobia, murder, SA jokes, the like - and stuff like suicide from here on]
Some of the tactics I include are:
Humanising the victims (e.g. "I feel for their family though - nobody deserves their kid to die like that" as a small aside for someone's queerphobic quip about a trans person who has recently died an early death due to suicide or murder.)
Refusal to engage
This can be not laughing at the rape joke, excusing yourself from a discussion when it gets gross, opting not to engage in a discussion about what "should" happen to an oppressed group or not to respond to a question etc.
Bringing in the historical context of the issue at hand
Just voicing dissent (e.g. "I don't agree" without dragging the discussion down into a debate)
Asking them to explain the joke or the argument (e.g. getting them to explain how the joke they made was yet-another example of The One Joke™ and being like "Eh, that one's a bit played out")
This one works well for when people are putting out snide insults that target you because it kills all the fun and they get deprived of their desired reaction from you.
Going Pavlovian on them
Idk how this works for other people but there are certain topics where I am like a dog with a bone. It's probably on account of being autistic. But whatever the case, I have 5 mins+ diatribes that people around me can trigger. Metaphorically, I will cling to the mic for dear life and I will talk my diatribe through until it's over. If you try to interrupt I'm either going to relate that directly back to what I was saying or I'm just going to continue on with what I was saying. This is a softer sort of redline for me in a social setting - basically I'm just draining all of the fun out of a situation and, after that same diatribe has been unloaded on a person multiple times, they develop an aversion to raising that topic around me again. Works for me. No doubt some people think I'm insufferable for it but idc much because if your opinions are insufferable then I'm just levelling the playing field.
Reframing the discussion
e.g. instead of going in on the discussion about George Floyd and the "need to maintain law and order", I'd shift the discussion to talking about police abuse of power as this is a much more serious problem and a much greater personal threat than whatever George Floyd did/may have done
Making it personal
e.g. asking them if they'd agree with that statement if it was their child etc.
I'm sure there are other tactics that I engage in too. But that's some of how I deal with it and what my strategy is as a person who is white and who more or less passes as cis, straight, a man, hetero etc.
How to lose friends and alienate people, eh?
I would reconcile yourself to the fact that you're going to crack a few eggs in the process of making this omelette.
Although — better fewer but better, as a wise man once said.
I would pick your battles, given that you are in a position to do you. You might be surprised at how far you can shift individual's perspectives if you take a gradual approach; it's very easy to denounce someone and cut them out of your life but, unless it's because you find their behaviour reprehensible, that generally only makes people more entrenched in their position. Sometimes allyship means being behind enemy lines and doing the hard work that the groups who you are an ally to are unable to, whether due to the fact that they aren't welcomed into the Old Boy's Club or due to the fact that they have to prioritise their own family/community/mental health.
In these situations I find that I am constantly engaging in a degree of calculus: how much goodwill and trust I have with this person, how much goodwill will be eroded by challenging them, how high a priority any particular issue is to push back on... basically it's weighing up how much far I am able to stretch the relationship without it snapping and how important it is to leverage the relationship for driving critical consciousness.
What that means is that I do not swing at every ball. Sometimes I let smaller shit slide in order to tackle the bigger issues. It sucks to have to compromise but this is the nature of doing hard work in the community and agitating for change. Sometimes I don't tackle that bigger issue head-on but I choose to voice dissent or to point out a pointed semi-rhetorical question before moving the conversation on.
[CW for mostly abstract discussions of everything awful - queerphobia, murder, SA jokes, the like - and stuff like suicide from here on]
Some of the tactics I include are:
Humanising the victims (e.g. "I feel for their family though - nobody deserves their kid to die like that" as a small aside for someone's queerphobic quip about a trans person who has recently died an early death due to suicide or murder.)
Refusal to engage
This can be not laughing at the rape joke, excusing yourself from a discussion when it gets gross, opting not to engage in a discussion about what "should" happen to an oppressed group or not to respond to a question etc.
Bringing in the historical context of the issue at hand
Just voicing dissent (e.g. "I don't agree" without dragging the discussion down into a debate)
Asking them to explain the joke or the argument (e.g. getting them to explain how the joke they made was yet-another example of The One Joke™ and being like "Eh, that one's a bit played out")
This one works well for when people are putting out snide insults that target you because it kills all the fun and they get deprived of their desired reaction from you.
Idk how this works for other people but there are certain topics where I am like a dog with a bone. It's probably on account of being autistic. But whatever the case, I have 5 mins+ diatribes that people around me can trigger. Metaphorically, I will cling to the mic for dear life and I will talk my diatribe through until it's over. If you try to interrupt I'm either going to relate that directly back to what I was saying or I'm just going to continue on with what I was saying. This is a softer sort of redline for me in a social setting - basically I'm just draining all of the fun out of a situation and, after that same diatribe has been unloaded on a person multiple times, they develop an aversion to raising that topic around me again. Works for me. No doubt some people think I'm insufferable for it but idc much because if your opinions are insufferable then I'm just levelling the playing field.
e.g. instead of going in on the discussion about George Floyd and the "need to maintain law and order", I'd shift the discussion to talking about police abuse of power as this is a much more serious problem and a much greater personal threat than whatever George Floyd did/may have done
e.g. asking them if they'd agree with that statement if it was their child etc.
I'm sure there are other tactics that I engage in too. But that's some of how I deal with it and what my strategy is as a person who is white and who more or less passes as cis, straight, a man, hetero etc.