I'm having difficulty internally dealing with some of my best friend's attitudes that I consider wrong and dangerous. He shares details of his life with me (and vice versa), even though he knows what I think about certain things. And I am also always very careful when sharing what I think or giving advice (even though we have a lot of intimacy and freedom to do so), because I know that I cannot and do not want to control his life, and that, within a friendship, we will disagree with things the other person has done or does, but we need to know how to deal with it and offer support when necessary.
That's what I've been doing and he always assures me of that too, that I'm not doing anything wrong with him, and that he would tell me if I crossed any limits. Today I decided (and told him) that since he already knows how I feel and what I think about certain things, whenever he does them again, I'll just say "thanks for telling me." Do you think I did well?
However, I admit that I can't get rid of this feeling of worry within me, or sometimes even upset with him (I don't dump it on him, I keep it to myself). Since I know I won't just be able to stop feeling this way (maybe over time), do you think I could do anything to get around these feelings? Because it feels so bad...
I know that the most important thing of all is to act cautiously and not let how I feel define who I am as a friend, and I think I've been able to do that. It's difficult to express my opinion and concern (when he gives me that opening) and at the same time not weigh in on him.
To provide more context; my friend constantly meets and has sex with other men through a dating app. I feel normal about it and I don't judge him. He always sends his location and the information of the person he is with to his boyfriend (open relationship). He always protects himself - sexually speaking - too. But I feel on alert when he sets up the first meeting at the guys' house, because then it's too dangerous and he puts himself in a very vulnerable position. In a person's house, they are the ones in charge, they are the ones who know everything about the environment... it's putting trust in a person he literally doesn't know. I already suggested "you would be safer in a motel, with other people nearby in case something bad happens", but he continues to do it, simply because it is more practical...
Okay, so the important thing to grapple with here is that when it comes to sex and dating, there is no universal ruleset beyond not abusing people that everyone has to be following. Some people are willing to take risks you aren't, or to engage in activities you wouldn't, and whether something is "too dangerous" is a very individual judgment, and not something other people or general guidelines get to dictate on your behalf. If he feels that sometimes having hook ups at other people's houses is worth the risks with the precautions he's already taking, you have to back off. You don't have to approve or even hear about it, but you have no right to tell him that it's objectively wrong or objectively too dangerous, because that's an individual judgment. You say that you know it's not your place to control him, and that you're working to manage your desire to step in, which is good - but you're clearly still making a universal moral judgment about his different risk assessment, and I think it's important to realize that actually you don't get to do that. As long as he's aware of the risks you think he's taking here, and he's willing to take those risks, it fundamentally comes down to respecting that in the end it's his judgment to make.