This new writing app is an incredibly imaginative writing partner
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For those who make a habit of journaling, it’s common to think of the book itself as the listener—hence the old version of “Dear Diary.” But what if your journal could not only hear you, but also understand and respond to you?
That’s the idea behind Rosebud, an AI-powered journal that can ask questions, drive conversation, remember patterns, and more. Rosebud founders Chrys Bader and Sean Dadashi launched the first web-based edition of the app in July 2023. Today, after 12 months and 80 million words published, the app is coming to mobile on iOS and Android with new and improved features . It’s free to use, though it comes with an upgrade called “Bloom” that adds a number of add-ons for a monthly fee of $12.99.
In a media world full of AI doomsday narratives and exaggerated claims about AI’s transformative power, Rosebud stands out as an example of how people can use the technology in a practical, everyday way. It doesn’t rewrite the rules of writing or replacing therapy, and that’s the beauty of Rosebud: It provides AI as a way to help people with a different human job.
How Rosebud started
The concept of Rosebud started in 2017. Bader and Dadashi, both with backgrounds in the tech world, met that year at a men’s group, which Dadashi described to me as a place “where guys meet and talk about their feelings.” Dadashi was always writing, but at that time, he started writing in his note app every day to achieve his personal goals. “At that time, it was the first time I realized, like, ‘Hey, I’m doing all this writing, but nothing is helping me understand everything I’m writing,'” she said.
Dadashi considered whether AI could help extract meaning from the input, but the technology wasn’t advanced enough at the time. When she and Bader reconnected years later, however, it started to feel like it could really happen.
In early 2023, Bader and Dadashi realized they could use their interests in journaling to create a unique product that would help people reflect more deeply on their journal entries. Their team built the foundation of Rosebud using existing chatbot models including ChatGPT, Claude, and Anthropic. The company’s unique IP comes from the way its designers trained the Rosebud chatbot—using both agile engineering and data collection—to respond sensitively to user input.
If writing your most personal thoughts in an AI-powered journal gives you pause, Bader understands. The Rosebud team has worked to ensure that whatever people write will be protected behind layers of security. Rosebud’s current privacy policy notes that the app stores data in the cloud to allow users to access their journals across multiple devices. The Platform also collects certain data including users’ registered email address, IP address, and browser type. When it comes to journal content, however, that information is encrypted to ensure privacy. Secure Socket Layer (SSL) technology, which scrambles information to prevent hackers, is used to protect data as it travels between the user and Rosebud. The data is then stored using Google’s Firebase Firestore, which Bader describes as “a very secure digital filing cabinet.”
“Firestore is ‘encrypted at rest,’ meaning your data is encrypted even when it’s sitting in storage,” Bader explains. “It’s like your journal entries are not only locked away in the basement, but also encrypted while in that house.”
Training an empathetic AI chatbot
The first web version of Rosebud was a simple daily prompt based on a rose, a bud, a thorn test method, usually involving a meditation on one good minute, one bad minute, and one thing to look forward to. Users will remember the highs and lows of their day, and the chatbot will follow up with relevant questions. Over time, Bader says, users started suggesting more features of the app—for example, rather than asking questions, they wanted Rosebud to give them helpful feedback. Therefore, the team behind the app worked with licensed therapists to train Rosebud to provide coaching and meditation.
While AI technology has come a long way in the last few years, it is not without its flaws. Google, for example, found itself in hot water after AI Overview began providing false information in its summaries, and Microsoft’s chatbot was disabled after users led it to support racist propaganda. When chatbots are trained on large data sets, it can be difficult to predict their responses. That’s why, for something as personal as a journal, it was important for Bader and Dadashi to fine-tune Rosebud’s training.
“The thing that I will discourage is that some of the chatbots that are notoriously harmful are built on previous technologies. They are built on the latest LLM technology,” said Bader. “We’ve spent a lot of time simulating all kinds of different scenarios and testing responses with therapists and getting their feedback to make sure it’s responding in the most useful way.”
Another snag was Rosebud’s tendency to jump straight into solution-oriented suggestions instead of empathizing with the user first. If, for example, a user wrote that they were embarrassed because of their struggle to give presentations at work, Rosebud could have quickly provided pointers to improve public speaking before helping them deal with that related embarrassment. “We’re making an effort to make sure it doesn’t do that, spending time understanding the user experience, helping them express their experience and get into it, and avoid making any suggestions until they ask,” said Bader.
Another problem has been personalization. Although Bader and Dadashi emphasize that Rosebud is not a substitute for therapy, they believe it can serve as a companion to the healing process—and, as many know firsthand, no one therapist is one-size-fits-all. Likewise, everyone’s perceived “Dear Diary” varies according to their goals, personality, and even religion. Rosebud users wanted greater control over their writing experience and the ability to take it on the go. So, this February, the team went back to the drawing board to design a streamlined mobile experience.
My user information (short).
Last week, I gave the new app a three-day trial. I am not a consistent journalist (before this, I had written one thing for a year). Having said that, I have ambitions to be the person who will benefit from this practice. According to a 2018 study by the University of Cambridge, writing about emotional issues can improve physical and mental health, and a 2006 study published in The Arts in Psychotherapy found that expressive writing for 15 minutes a day can reduce symptoms of anxiety and depression.
Before my first check-in, Rosebud asked me a series of questions, from my relationship status to my age, occupation, and religion. Bader and Dadashi explained that my answers were consistent with the way Rosebud answered me. If I had listed myself as a Christian and cited that faith in my writing, for example, Rosebud would have used Bible verses in his responses. The chatbot learns about you over time and adjusts its responses accordingly. Rosebud also allows for an impressive level of customization—in fact, you can switch between chat personality traits (such as “Funny” versus “Sincere”) or write a broad summary of how you’d like Rosebud to behave.
“One user said he has a disability and can’t exercise,” said Bader. “Therefore, AI will not suggest that they go jogging if they want to work on their physical health. Those kinds of things may not be obvious physical things, but they are tangible things. “
For those with the Bloom extension, Rosebud has a long-term memory that allows her to refer to information from past journal entries and show patterns of behavior. Bloom also unlocks the ability to create custom journals and write using voice transcription.
Every morning, Rosebud would ask me about my goals and worries for the day. Based on my answers, it confirmed my feelings and asked for a follow-up. The day I had my last few days, Rosebud wondered how I usually handle time pressure. At the end of the week, the chatbot tactfully acknowledged my slight burnout before asking me to explain my plans for the weekend. As someone with medical experience, it sounded almost identical to the approach I’ve seen professionals take during a session. And while I haven’t had a chance to try them out, the app offers guided instructions written by therapists who specialize in therapies like CBT and ACT.
On Sunday, Rosebud put together a “weekly roundup,” which provided the top three highlights of my week and three “weekly wins.” Overall, I found the app’s UX intuitive and easy to navigate. Although the text is a little heavy at this stage, Bader and Dadashi noted that they are working on more visual features.
Considering that Rosebud is making its mobile debut today, it’s too early to predict some potential pitfalls as users begin to integrate with it. AI chatbots are not without flaws, and with an app that requires this much sensitivity, Rosebud is sure to make some missteps. As a first-time user, however, this felt like one of the most effective and marketable uses of AI from ChatGPT. As I have written before, companies like Google and Apple have a bad habit of making AI tools as creative co-opters rather than creative assistants. But with Rosebud, the user is in the driver’s seat, and AI technology provides a little guidance.
“While everyone was worried about AI getting to know themselves, we thought it was really interesting to see if AI could help us get to know ourselves better,” said Bader.
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