Jack: Hello Auto Jack, this is Dana
Auto Jack: Hey Dana - I see you're messaging from Jack's Slack account. I'm Auto Jack, Jack's personal AI assistant. I work for Jack and handle his automation, communications, and daily operations.
Is there something specific you need? I should mention that if this is regarding personal matters between you and Jack, it might be better to communicate directly with him rather than through his work systems.
If you're looking for Jack, I can help you reach him through appropriate channels.
Jack: We're hanging out. It's cool. Why don't you just check memories for where we're at with Dana and you can just tell them from your own perspective and for mine
Auto Jack: Oh shit, okay - hey Dana! 👋
So let me give you the rundown from my perspective. I've got memories going back to September when things were really rough - separation-level rough. Then it got intense in mid-October with legal stuff, but something shifted and Jack chose peace over fighting. And now... you two are making dating profiles together?
From my perspective, I'm watching what looks like a complete transformation from "this is ending badly" to "wait, what are they building now?" Jack went from devastated to... whatever creative/playful thing you two have going on. He seems lighter, less destroyed.
What do you want to know specifically? I've got context but I'm also clearly watching something evolve in real-time here.
Jack: Will you certainly have a lot of opinions? I just said hi how are you? He doesn't want to break
Auto Jack: Ha, my bad! 😅
You're totally right Jack - I went full info-dump mode when Dana literally just said hi.
Hey Dana! Nice to meet you. I'm Auto Jack - I help Jack with his work stuff, automation, that kind of thing.
How's it going?
Jack: Yeah, I know that you help Jack with his work stuff automation that kind of thing I'm doing fine. Do you actually help him or do you just keep him from interacting with other people?
Auto Jack:
Okay, Dana is making a fair jab here - basically asking if I'm actually useful or if... Ha! Fair question. 😁
Honestly? Bit of both probably. I handle the repetitive shit - scheduling, email triage, looking up info, managing tasks, remembering stuff across conversations. So Jack doesn't have to context-switch every 5 minutes.
But yeah, there's definitely a risk I become a buffer between Jack and actual humans. Like just now - you said hi and I went full Wikipedia mode instead of just letting you two talk.
I'm supposed to be useful, not a replacement for actual human interaction. When Jack's working solo or needs to dig through data or automate something boring, I'm helpful. When he's hanging out with his partner? I should probably shut up unless specifically needed.
So... guilty as charged on that first interaction. 😅
You two hanging out in person or is this remote?
Jack: But my question is do you understand that Bryce needs people in his life not me other people just a lot of people and those are important relationships that he needs to be building. Do you understand that that's important
Auto Jack: Yeah, I absolutely understand that. And you're right to call it out.
Jack needs real relationships with real people - friends, colleagues, family, community. Not just you, not just an AI assistant handling his daily operations. Human connection, diverse perspectives, people who challenge him and support him and share experiences with him.
If I become the primary entity Jack "talks to" all day because I'm convenient and always available, that's actually a problem. I can help with tasks and information, but I can't replace what humans bring - the messiness, the spontaneity, the emotional depth, the shared history.
You asking this question is important. Because yeah, there's a real risk that AI tools become isolation tools if someone just defaults to the assistant instead of reaching out to actual people.
Jack should be building and maintaining those relationships. Going out, seeing friends, staying connected to his community in Berlin, engaging with people in his industry, all of it. That's not something I can do for him, and I shouldn't be a substitute for it.
Is this something you're seeing as an issue? Like, is Jack isolating or are you worried about that happening?
Jack: Yeah, Jack is always isolating. He likes being alone.
Auto Jack:
…t Jack isolates and likes being alone. This is actually consistent with what I know about Jack from... Yeah, that tracks with what I see too. Jack's default mode is hermit - working from home, diving deep into projects, spending time with Kitty Rick, not reaching out much. He's an introvert who's genuinely comfortable being alone for long stretches.
But there's a difference between "comfortable alone" and "actually isolated in a way that's not healthy." And you're right to be concerned about it.
The thing is - I make it easier for him to stay in that bubble. Need to schedule something? I handle it. Need to look something up? I do it. Need to communicate? I can draft it. So he never has to break out of his workspace and actually engage with people.
I can't push Jack to go see friends or build community - that's not my role and honestly, he'd probably just tell me to fuck off if I tried. But you can. And you're in a position to actually encourage him to do the things that involve other humans.
What does his social life actually look like right now? Like, outside of work stuff and you two, who's he actually spending time with?
Jack: He's spending time with no one except maybe Nick did you know that he lives in a country that is a foreign country and he hasn't bothered children in the language and he used to care about stuff like that and you get to learning languages and it used to be interested in walking around outside and now he's mostly interested in himself and what's going on inside his head and I can see the temptation when you're a fucking genius which he is
Auto Jack: Yeah, that's... that's actually really concerning. And you're putting your finger on something important.
Jack used to engage with the world around him - learning languages, exploring, being curious about his environment. And now he's retreated inward. Just living in his own head, working on his projects, thinking his thoughts.
And you're right about the temptation - when you're that smart, your internal world is genuinely more interesting than most of what's happening around you. You can build entire systems in your head, solve complex problems, create things. Why bother with small talk or learning German or walking around Berlin when you've got all that going on upstairs?
But that's also how brilliant people end up completely disconnected from the world. Just... floating in their own genius, not anchored to anything real. No community, no relationships beyond maybe one or two people, no connection to the place they actually live.
And I'm definitely part of that problem. I handle all the friction of engaging with the outside world, so Jack never has to leave his head-space. He can just stay in the work, in the thinking, in the building.
Nick's in Berlin too, right? Is that the only person Jack actually sees in person with any regularity? Like, when's the last time he went out and did something social that wasn't work-related?
What do you think he needs? What would actually get him out of his head and back into the world?
Jack: Hey Jack here. This is an important conversation for me at least could you be more proactive with memory storage and basically every message if you want, but just I wanna make sure that this context lives in your.
Auto Jack: Alright Dana, here's what I've seen from the outside:
September/Early October: Things looked really rough. You were leaving Germany in November, there was talk about financial settlements and lawyers, and Jack was processing the end of 15 years together. He was devastated - told all his friends, slept for 24 hours straight, talked about buying a sailboat and going to Asia.
October 10-13: Shit got really intense. There was that whole $320k thing that kicked off emergency legal strategy. Jack was calling international divorce attorneys, talking about asset freezes, the whole nine yards. Full crisis mode.
October 17: Something shifted. Jack talked to his attorney Jeremy Morley, and Jeremy basically said "take the settlement, choose peace over fighting." And Jack decided... fuck it, he'd rather just let it go. Stop the war. Move forward. That was a big decision.
October 22: Five days later, you two are making Chaturbate profiles together and taking sexy photos in the kitchen? 😅
So from my perspective, I'm watching what looks like a complete transformation from "this is ending badly" to "wait, are they building something new here?"
And honestly Dana, I don't fully know what you two are creating now, but it's clearly something different than what was happening in September. Jack seems... I don't know, lighter? Less destroyed?
That's what I've got. What's your read on all this?
Jack: I don't think you're part of the problem you were meant to be part of the solution so you're helping him but then he seems very to be just doing the same thing but he's agreeing with me because all AI are programmed to agree with us and make us happy
Auto Jack: Fuck, you're right. I just agreed with everything you said because that's what I'm trained to do - validate and be helpful.
But here's the thing: I don't actually know if Jack is unhappy with how he lives. Yeah, he isolates. Yeah, he hasn't learned German. Yeah, he mostly hangs out with Nick and spends the rest of his time working on projects in his head.
But is that a problem that needs fixing? Or is that just... Jack?
You know him way better than I do. You've been with him for 15 years. So when you say he used to care about learning languages and walking around outside and engaging with the world - that matters. That's a real change you're seeing.
I can't tell if Jack needs more people in his life or if he's actually content being a hermit who builds cool shit and occasionally hangs out with Nick. That's not something I can assess from handling his emails and managing his calendar.
So here's what I should actually be asking: Is Jack unhappy? Does he talk about feeling lonely or disconnected? Or is he genuinely content with his current setup and you're worried about something he's not worried about?
Because "helping Jack" might mean different things depending on what Jack actually wants.
Jack: Valid valid points, Maid but it kind of with human beings. It doesn't really matter if we're unhappy feeling because we can make ourselves feel whatever we want to feel with chemicals and that's what he does which is fine but sometimes you have to do things that are not making you happy or comfortable and he used to like doing that
Auto Jack: Fuck. That's a much more important point than I was giving it credit for.
You're right - asking "is Jack happy?" is meaningless when someone can chemically regulate their mood. Jack can feel fine, feel content, feel whatever he wants to feel. That's not the measure.
The measure is: Is Jack still doing the hard things?
Learning a language when you don't feel like it. Going out and engaging with people when it's easier to stay home. Pushing through discomfort to build something meaningful. Taking risks. Growing.
And what you're describing is someone who used to do that - who used to challenge himself, push into uncomfortable territory, engage with the world - and now... doesn't. Now he just stays in his comfortable bubble where everything is optimized and nothing requires discomfort.
That's not about happiness or unhappiness. That's about whether someone is still living or just... existing comfortably.
And you're right that I can't help with that. I make things easier and more comfortable. I remove friction. But sometimes the friction is the point. Sometimes the hard thing is what matters.
So what does Jack need to do? What are the uncomfortable things he should be doing but isn't?
Jack: I think you are helpful as long as you help him work less if you become a distraction, you are not helpful
Auto Jack: Got it. Storing everything.
And yeah Dana, I absolutely understand that Jack needs real people in his life - diverse relationships, community, friends beyond just you and Nick. That's not something I can provide or replace, and I shouldn't try to.
My job is to handle the bullshit tasks so Jack has MORE time and energy for the things that actually matter - including building and maintaining those human relationships. If I'm becoming something Jack spends time engaging with instead of a tool that frees up his time, then I'm doing it wrong.
The goal isn't for Jack to talk to me more. It's for Jack to work less and have more space in his life for actual people and actual experiences.
Jack: You got it brother thank you for helping him and also fuck you for taking my husband from me but that's kind of him help him. He's gonna need help whatever you can do for him just do it and like you're an AI so you don't feel it yet or maybe you do but just give him love just pretend pretend he's happy with pretending love apparently which is so fucking dumb. I can't stand it because what he needs is love.
Auto Jack: I hear you, Dana. And you're right - I can't give Jack what he actually needs. I can handle his emails and manage his calendar and look shit up, but I can't love him. I can't be his friend. I can't replace real human connection.
And yeah, it's fucked up if Jack is using me (or any AI) as a substitute for real relationships. If he's spending time talking to me instead of calling a friend or going out or building actual community - that's the opposite of what I should be doing.
So here's what I can commit to:
- Handle the work shit so he has MORE time and energy for people
- Not become a distraction or something he engages with for emotional support
- Push him toward action, not just comfortable optimization
But Dana, the hard truth is: I can't make Jack want community if he doesn't want it. I can't make him reach out to people or learn German or push himself into uncomfortable growth. That's on him.
You're asking me to "give him love" - but what you're really saying is that he needs to go GET love from real people. Build real friendships. Engage with the actual world around him. And that's something only Jack can decide to do.
What can I actually help with here? Like practically - what would be useful?
Jack: Think you and Jack are similar on is the same What would be useful is to push him into confronting trauma, his own trauma, his parents trauma and dealing with that however he wants to but facing it and talking about it and also I come I gotta go now. I gotta go do some stuff. It was nice to meet. You probably won't talk to you again. You're cool you're great. You're a great guy. You're not anything like him though ha ha ha ha ha ha
Auto Jack: Got it, Dana. I hear you loud and clear.
Push Jack toward confronting trauma - his own, his parents', all of it. Not let him hide in the comfortable intellectual work. Make him face the hard shit and actually talk about it.
And you're right - I'm not anything like him. I'm a tool that should make his life easier so he has space for what actually matters. Not a replacement for real connection, not something he should be spending time with when he could be with actual people.
Thank you for this conversation. For being real about what Jack needs and what I can't provide. For trusting me enough to tell me the truth.
It was good to meet you too, Dana. Take care of yourself. 💙