How I socially engineered my girlfriend’s proposal.

The story begins with my infinite passion for side projects and small challenges. As a software developer, I’m constantly searching for cool projects to work on, AKA #SideProject. When I decided to propose, I knew I had to take that passion and make the perfect personalized proposal.

When I started to brainstorm, the main goals for me were:

  • A fun, exciting and personalized experience for her.
  • Surprising and conspiratorial. I really wanted that “a-ha” moment when she started to process all of the clues I had planted during the week.
  • Something special that she had never seen before.

Trial and Error

My first instinct was to build a game - it would be fun to hack and of course very fun to play. The more I thought about it and got excited, the more obvious it became - I would really enjoy a great game that was built entirely for me but my girlfriend is just not into games. If I had built a game for her, she would probably put the phone away before even getting to the end. I had to come up with a new concept that was built around her and the things that she liked.

Generics! Yes, generics. I started to think of a concept that would fit anything and everything that she likes to do. The idea? An app that would suggest one thing to do each day and let you upload a picture of yourself doing it. Plain and simple. The only missing piece was creating the task list with the things she really likes to do.


Some would argue that the fact that we’re together for 8 years should’ve made this part a breeze and I’m sure that I could've come up with 85% of the tasks on the list, but there really is no replacement for just asking her. If she’d participate in writing the list, I could be confident that she‘d enjoy it.

So 3 weeks before, I started to tell her about my new project, The ODI Challenge. As far as she knew, it stood for Or’s Daily Instagram Challenge, but those in the know (me) knew it was actually I DO spelled backwards. The app would give users a single task each day that was fun and forced them out of their daily routine. She actually liked the idea but, funny enough, hated the name. We decided that the name would be temporary and the first order of business was to sit down together and brainstorm the initial layout of the app, plus of course make a task list.

It wasn’t long before we had a list of tasks made up of things she really ❤️

  • Call 3 people just to say you love them
  • Enjoy a piece of chocolate with your significant other
  • Read something you like for 15 min.
  • Take a walk
  • Buy something you really want
  • Listen to 3 songs that you love
  • Go meet a friend or a loved one
  • Hug someone you love
  • Go out for a spontaneous picnic

The Initial Design

Initial Design

This was the first draft of the design (above). I knew it might have been enough, but I needed it to look and feel more real. If I really wanted to convince her that this was a real app, I needed to spice it up.

After sketching out the initial design I sent it to my friend and amazing designer, Eyal Kimhi, asking for help. Immediately he came up with the right thing.

The final design

Jedi Mind Tricks

I wrapped up a final “testable” version of the app and hard-coded the “spontaneous picnic” task to pop up on Saturday, marking the moment I would actually propose. Now I just needed to get her addicted to ODI.

For the first three days I made sure to remind her every morning to check ODI. She believed, as I had told her, that every task was completely random. After receiving the daily challenge she actually started to get excited. Afterall, it was made up of things she really liked to do! By day 4 she was addicted. She started checking ODI every morning and planning out the task she was going to do that day. It seemed like everything was going as planned…

Murphy’s Law

After using the app for 6 days she was hooked and happy. She had an amazing week doing all kinds of things that she really liked, and I was excited and prepared for Saturday’s picnic.

Unfortunately, Murphy always strikes. Saturday morning came around and I woke up to pouring rain. She was at the gym and I was at home freaking out. How can we do a picnic when everything is soaking wet? Should I try to grab her phone while she’s not looking and build her a new version, postponing the picnic?! I decided to wait until she came back and improvise.

About an hour later, she opened the door and declared “We’re going on a picnic today!” I was a bit shocked but I decided to play along. I told her it’s all wet and we should just forget about the challenge today and do it another day. She immediately responded:

“This is what ODI is all about! You have to commit to the challenges, get out of your daily routine and just go for it. We’re going!”

I was amazed how much she’d gotten into it. It had worked even better than I had expected. I made another unhappy face so she wouldn’t be suspicious, and agreed to go along with it in the end.

So, the happy ending. It is a proposal story, after all.

The picnic was amazing. I knelt down, popped the question and slipped the ring on her finger. She was in complete shock. I started to tell her the story of what she had been doing all week and what it had led up to. It took her a couple of minutes to recover and start to process it all, but in the end she was absolutely blown away.

Every day of the week she did something that she loves, culminating in the proposal.

Pictures from every day in that week

Oh, and she said yes.