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I don't want to discuss dating with a friend, and they walk to talk more.

He’s now asking where to take a date in my town. (He loves two hours away.)

I suggested he ask his date.

There’s got to be another way to stay in the relationship but not keep being asked scout dating…
 
There’s got to be another way to stay in the relationship but not keep being asked scout dating…
If he’s the kind of person that needs his hand held?

It’ll be the next job-hunt, house-hunt, grant-writing, car-buying, clothes-shopping… unless the person he’s dating holds his hand through those oh so scary things… leaving you with actual person status.
 
That’s the weird thing. He does those things just fine all the time with no handholding. That being said, he does feel victimized quickly over small things where I don’t see any harm intended or done. It’s almost bordered on paranoia now and then.

Maybe he feels victimized by women who have rejected him and I’m an easy representation of women he can dump the negativity on… it won’t stop. It will just shift subjects, I gotta avoid it.

People are messy.
 
That’s the weird thing. He does those things just fine all the time with no handholding. That being said, he does feel victimized quickly over small things where I don’t see any harm intended or done. It’s almost bordered on paranoia now and then.

Maybe he feels victimized by women who have rejected him and I’m an easy representation of women he can dump the negativity on… it won’t stop. It will just shift subjects, I gotta avoid it.

People are messy.
He seems to hyper-focused on this subject. I can’t remember if you said he had some sort of trauma or mental illness but it’s not healthy that he can’t stop telling you about it. Maybe can poach the subject with him. Some self-awareness and discipline is needed here.
 
I don't think I quite have a handle on the difference between listening and being there for a friend... and being a person people like to just dump on...
The difference is that the people who just want you to listen, manage their own emotions. This guy expects you to emotionally regulate him, which is not reasonable to ask of a friend.

Some people just like to vent, but make it clear that they are just venting to be heard and don't actually need a solution or advice (thus they're managing their own emotions). Others, like this guy, are forcefully pushing your stated boundaries because they're "distressed" and need you to "fix it." That isn't a friend, it's a therapy patient.

I'm not a good friend in general so take this with a grain of salt, but: whatever the reason for his insecurity honestly... isn't your problem. Maybe he got victimized by a woman, maybe he is redpilled, maybe he is OCD. Maybe he is asocial. Or maybe it's a combination of everything. But you are not obligated to investigate and solve it for him.

You can, if you want to. It is a nice thing for you to try and do. But if he's hinging the friendship on this then he isn't asking for you to be nice. He wants you to be responsible for his feelings.
 
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I told him about a week ago when dating was not a topic that “I’m going to skip any dating conversations. It’s not a topic I am going to discuss.” Simple, clear…

I then messaged about a non-dating topic.

A few days later he messaged that if I ever want to know how great speed dating is, to let him know. Today he messaged about feeling stressed about dating. He listed other things, excitement about a trip; etc. He didn’t really go into details he also did bring it up again,

I’m of two mindsets. On one hand, this shouldn’t bother me.

On the other hand, it does bother me. If someone says dogs freak me out I am not going to talk about dogs… I don’t keep messaging that person about dogs. I love dogs but I also can respect someone else is not in the headspace to talk dogs…

This dude?

I’m totally okay with venting about life, etc, but there is no aspect of dating I want to discuss with him or have him discuss or talk about with me.

What is the point of knowing someone is not going to talk about a subject and to still bring it up with them?

It pisses me off because it feels manipulative. But like… come on… I shouldn’t micromanage friends right and instead just let them be themselves… and then choose if I want to engage with them or not.

And it seems foolish that this is such a dealbreaker for me. But it’s getting there. It’s almost not about dating anymore. It’s about something I needed and stated being disregarded.
 
It seems you have turned yourself inside out trying to get through to him, some extraordinary blinkers he has there. Agree, this is about something else, not just dating. He doesn't seem to care one bit about your stated boundaries. Or even notice anything you've said about them.

I guess it's fair to say he isn't going to hear what you say about this.

Do you think it's worth continuing to talk about it with him?

I'm not asking if you want a friendship with him, but if it is worth continuing to talk about this with him.

I'm guessing already if he talks about dating you leave or put the phone down?
 
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I guess I find it baffling. Maybe because this feels kind of common in my life? I’m not meek, I can be quite clear… I know this person cares about me, they have shown it in other ways.

And yet here we are. I’m feeling unheard and frustrated.

It’s not a deal breaker, it has become much much less, but it’s still a subject. When it’s a friend of a few decades, this isn’t enough to throw out the friendship.

And it’s the battle, what to accept, what to let go, what to speak up about, what to just endure… this one, for now, I think is a wait and see. When he brings it up again, I’ll ask what he’s seeking by asking me about it after I’ve said I can’t go there with him. Just be curious about his goal when he knows I’m not okay with this. Well, try to be curious anyhow.
 
I guess I find it baffling. Maybe because this feels kind of common in my life? I’m not meek, I can be quite clear… I know this person cares about me, they have shown it in other ways.

And yet here we are. I’m feeling unheard and frustrated.
Because it’s not about you / not in your control?

It’s about you them, who they are, and how they need to be(rather than something they can change, easily ((Oh! Sorry!!!)), on request).
 
@Justmehere , from what you've said the only thing you've left out is how it makes you feel. Could you say, the topic makes me feel sad and uncomfortable, and I appreciate you trust my opinion but I feel unheard and disrespected when you keep asking? (Or something similar/ whatever is authentic). Because if you are friends surely give him the benefit of the doubt he doesn't want to hurt you nor you him? I think it's the part (how we feel) that often doesn't cross our minds to include when we communicate if we are more avoidant. Then our feelings (which we didn't ourselves perhaps acknowledge or the gravity of them and did not communicate) feel disregarded and our perception likely alters accordingly, and we feel hurt or frustrated or unheard or of no importance, etc. Same thing to say (x, y or z) is very important to me. Maybe to some it isn't, but for you it is. And honesty, saying I'm running out of ideas here and don't want to hurt your feelings but it's not personal, this topic makes my skin crawl, it's too much for me to bear without feeling badly.
 
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