Ditto
The Ditto app was an ambitious product designed to foster stronger, healthier relationships—but despite our best efforts, it ultimately failed.
While at Headway — design and development agency, I worked on the Ditto app. In 4 months, our team took the app from concept to launch. As the sole designer, I led the branding and mobile app design*, collaborating closely with the founder, couples, counselors, and our team to ensure every feature was rooted in real relationship practices.
While we delivered a polished product on time, challenges with founder constraints and a lack of clear product ownership hindered its success.
*for this case study I will focus on the app design process
Our goal was to create a space that supports couples in building deeper connections through meaningful conversations and intentional habits.
Research
Couples and relationship counselors use various methods to strengthen bonds—whether through journaling, open-ended conversations, or building small, meaningful habits. However, these tools often exist offline or across disconnected systems, leaving room for frustration and inconsistency. We saw an opportunity to centralize these practices in a mobile-first app that could seamlessly integrate these rituals into couples’ routines.
To align our design with real-world needs, we worked directly with couples and counselors, understanding the specific practices that worked for them.
We learned that couples wanted a tool to:
- Capture important memories and moments together.
- Encourage open and honest conversations regularly.
- Build consistent habits that foster connection.
Feature Definition
From these conversations I was able to begin concepts and mapping user journeys until we narrowed to three core features that reflected the most effective practices couples and counselors already used.
Concepts take shape
Three Core Features
01 The Story of Us
A journaling tool for couples to record special moments, dates, and anniversaries to reflect on their shared journey.
02 Love Honestly
A conversation starter that sends couples weekly questions, encouraging them to answer honestly and share their responses, sparking meaningful conversations.
03 Love Habits
A habit tracker designed specifically for couples to cultivate small, intentional habits together.
Ditto Design System
As the designs for Ditto began to take shape, I developed a design system to ensure consistency across the app, branding, and website. This system streamlined collaboration, provided reusable components, and created a cohesive user experience from start to finish.
Testing
We revisited the couples and counselors from our early research sessions to test our prototypes and app features with them. Their feedback was invaluable, helping us refine the experience, validate our concepts, and ensure the app aligned with real relationship practices.
Overall the feedback was positive, the founder was ecstatic, our team was stoked.
Launch
The app was launched into the Apple and Android app stores.
Outcome
Fail 😞
Despite successfully delivering a polished product within the timeframe the app failed to gain traction and meet the intended outcomes. Within three months it was shuttered.
Unfortunately, several factors beyond our team’s control contributed to the project’s struggles:
- Founder Constraints: Key strategic misalignments with the founder regarding long-term vision and priorities affected the project’s trajectory post-launch.
- Lack of Clear Product Ownership: Although the team worked hard on the product’s core, changes in leadership focus meant that critical business and marketing decisions were delayed, stalling momentum.
Reflections and Learnings
While the app ultimately did not achieve long-term success, the experience was an invaluable learning opportunity. Here were my key takeaways:
- The importance of alignment between design, business, and leadership: Having a strong vision from the top is essential for the product’s sustainability post-launch.
- Move fast, but plan for sustainability: Shipping in four months was exciting, but product success requires consistent post-launch support, especially around marketing and product ownership.
Conclusion
Although the Ditto app did not reach the success we envisioned, the project demonstrated my ability to design a product from 0 to 1 within a short timeframe. I created a thoughtful experience for couples with The Story of Us, Love Honestly, and Love Habits—features designed to spark meaningful interactions.
Despite the challenges, I am proud of what we built and the collaborative effort that brought it to life. This project was a reminder that great design needs strong leadership and strategy behind it, and moving forward, I’ll apply these lessons to future projects.
United Masters Wallet
