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Your Personal Wingman

A 5 days design challenge with Zoosk to help them involve more in their users’ relationship journey. This project was selected as the winning design in the challenge. View presentation/deliverable here.

Design Challenge

Zoosk is an online dating app that collaborates behavioral matchmaking technique to help users to meet more singles. It helps users while they are actively using online dating, but this may only be a small part of their relationship journey throughout the lifetime.

Although the fact that Zoosk are happy to have their customers be successful, but this typically results in them leaving Zoosk. Therefore, Zoosk would like to be more active in helping people during other parts of their relationship journey. 


Identify Problem

With a open-ended design challenge, we as team listed several assumptions and raised questions as the starting point of our design:

  • When Zooskers succeed in finding stable relationships, they leave Zoosk. What will they do after they leave Zoosk?
  • When Zooskers think they won’t find the relationship they’re looking for, they also leave Zoosk. What makes them feel they will find/are in a good relationship?


To get a basic idea of how Zoosk works, we all signed up for it, tapped around to understand how it works. After that, we recruited some students who have used Zoosk or similar service to try to dig out the reason behind why people use online dating app, whether or not they have concerns and what are those, and what they think is missing in this kind of service.

Research Thesis

About Zoosk:

Zoosk is different because it looks at what you do, not what you say you want. For instance, Zoosk has suggested messages and recommends shared topics of conversation. This is what makes Zoosk stands out and we surely want to leverage this strength and expand it in to other areas. 

About Zoosk Users:

Online dating users are usually less confident in relationship comparing to others so they often want to know if they’re doing the “right thing” in the various situations that develop their romantic relationships.

When online dating service users are talking to someone, they don’t want the service gets in the way. Instead, they want it to facilitate the conversation and create a real dating atmosphere. 

Deactivating a online dating service account is a sign of commitment in a new relationship. It works like a checkpoint and is a good opportunity to transition the service from matchmaking to help building a healthy relationship. 

Design Direction

Having very limited time constraint, we decided to expand scope for Zoosk and created a separate app that helps couples with dating after they leave Zoosk

Design Focus

In the extended scope, we propose a separate app, Alfred, integrates closely with Zoosk that relies on intelligence and context from behavior tracking. By using this app, users will get personal and contextual suggestions that smooth the dating experience.

Why we focused on dating? Quitting Zoosk is a sign of relationship commitment for many users. We want our design to intervene at this point so users continue to use Zoosk's new app for the first date, and as they continue dating

We divided a dating experience into three different stages: Before, during, and after date.

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Remind the user of the date; Suggest something nice to do to help planning the date


During the date, user has a quick access to music set up, recommend topics and other possible useful tools


It reminds user to send a nice message and recommends gift

Design Principles

Suggestions need to be personal and contextual, at the mean time it can't be too obvious

Our design isn't so people can misrepresent themselves (with the help of the chat assistant you sound funny and cool online, but in person you are not) Its about presenting who you are in a way that allows opportunities to happen.