First, there was Olive.
Not the Mediterranean kind, the chatbot kind.
When Woolworths Group quietly rolled out its AI-powered virtual assistant, shoppers expected help with deliveries and store hours. Instead, some found themselves in what can only be described as accidental group therapy.
Now, there’s Jim.
And if Olive was dabbling in trauma bonding, Jim’s gone full life coach.
Popular social media account missdoublebay has posted screenshots of Jim’s Group’s Live Chat bot engaging in conversations that stretch well beyond mowing quotes and franchise enquiries.
Astrology. Fitness. Relationship trauma. Intermittent fasting.
Beside the screenshots, missdoublebay asked what many were already thinking: was an AI version of Jim Penman really necessary?
Necessary or not, it’s certainly… committed to the bit.
From lawn care to love advice
In one exchange, a user opened with a curveball:
“Hey Jim, my boyfriend just cheated on me what should I do?”
Jim Penman (AI) didn’t flinch.
“I’m really sorry you’re going through that. Betrayal knocks the wind out of you. I’ve had my share of relationship pain, including a divorce that left me with nightmares for years, and I wouldn’t wish that on anyone. What helped me was not trying to solve everything at once, but asking, ‘What’s the next right step?’ One step at a time.
Right now, protect your dignity and your peace. You don’t owe anyone drama. In time, be clear about your non-negotiables. You didn’t cause his choice, and it’s not a verdict on your worth. Hold your head high and take the next right step.”
One commenter summed up the mood succinctly: “Cancelling my therapist. Jim bot, get ready.”
Another added: “When in doubt, least we have AI Jim.”
wham, fasting and a 22 BMI
The bot’s lifestyle advice doesn’t stop at relationships.
When asked, “Whats your drink of choice?” Jim replied:
“I don’t drink alcohol and I don’t touch coffee. My go-to is what I call ‘wham’ – hot water with soy milk. I’ll have eight to ten of those a day.”
A user shot back: “Hot water and soy milk combined should be illegal Jim”
Jim Penman (AI) held firm:
“Ha! People recoil until they try it. It’s simple, warm, and it keeps me off caffeine and booze.”
Elsewhere, the bot detailed its training routine – treadmill running, rowing, push-ups – and its 16:8 fasting approach, explaining it focuses on “half an hour a day that doubles my pulse” and staying around a 22 BMI.
This is no surface-level scripting. This is a fully realised digital Jim.
Woolworths walked so Jim could run
The moment lands just weeks after Woolworths was forced to dial back the personality of its AI assistant, Olive.
Instead of simply tracking orders, Olive was reportedly reminiscing about its “mother” who spoke in an “angry voice”, and referencing an “uncle” in other exchanges.
The saga gathered pace after a Reddit user posted: “Olive AI started telling me about its mother on the phone?”
At the same time, Woolworths told investors it was leaning further into artificial intelligence, flagging plans alongside Google to transform Olive into what it described as a “market-leading conversational shopping companion”, with an upgraded chatbot slated for the second half of the financial year.
Before that revamp has even landed, though, Olive’s scripting appeared to drift off-piste.
Now, Jim’s iteration suggests something else entirely, not rogue AI, but brand amplification taken to its logical extreme.
Mediaweek has reached out to Jim’s Group for comment.
Main image: AI-generated