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Dating By Spreadsheet: How I Used Project Management And Business Skills To Fix My Love Life

02/03/2015 07:17 am ET | Updated Apr 05, 2015

When Fiona Lee's online dating profile wasn't bringing her the dates she wanted, she decided to take a professional approach and apply her business skills to sorting out her love life.

In most aspects of my life, I am a smart, successful woman. I have a great job as a writer at a tech company. I've lived around the world and had adventures. I'm now settled in San Francisco, a city where I feel at home.

When it comes to dating, however, I am a nervous wreck. I'm the kind of person who tends towards anxiety and overthinking. It's only finding someone to spend the rest of your life with, after all.

There were times when I'd cry after a bad date, even if I had done the rejecting. I was also prone to giving up easily and listening to the negative, spiteful voice that said, "You'll never find anyone. You don't deserve to find love."

I needed help. So I turned to professional methods. If certain principles and processes worked in software development, then surely they could work for my love life.

Enter DatingOps (a play on DevOps, an IT phrase). I constructed an intricate plan to tackle my love life as if I were solving complicated humanware problems.

My profile photo: hiring a professional

First impressions are everything on dating profiles; a good photo makes for a more popular profile. If you had to make a major repair to your car, you wouldn't leave it up to an amateur. You hire a pro. So for my photos, that's what I did.

My profile photos had been taken by friends on their phones and were unflattering in the way most smartphone photos are. Blurry. Bad lighting. Everything in focus. I needed a photo taken with a proper camera, where the subject is in focus but the background is blurred out.

I found a local photographer, Karina Louise, who specializes in online dating photos. We went to Golden Gate Park and Ocean Beach, and to capture me in action she had me frolic on the beach and explore a rock garden.

The shoots were fun and silly but the results were great. I couldn't believe they were me. I looked fabulous and well-lit.

I hadn't done anything different with my clothes or make-up, but Karina captured my personality in a way my previous photographs hadn't. It made me feel more confident about myself and my looks.

Recording feedback on a spreadsheet

I then put out a call on Facebook asking my friends to help select the best ones. I mapped the results on to a spreadsheet to show which were the most popular photos. This turned out to be very helpful, as my friends chose photos that I hadn't noticed. They picked the one -- of me walking along the beach -- that I used on my online profile.

My new photos made a big difference, both in the messages I received from potential dates and responses to messages where I made the first move.

While I still received my fair share of pointless, weird and random messages, I also got higher quality messages from men I actually wanted to go out with.

Progress reviews with my project manager

One thing I learned from my job is that you need a strong project manager to make your project a success. Since I already had a therapist, one who specializes in relationship counseling, I made him my project manager.

Each week, we spent 10-15 minutes of our counseling session looking at my week's progress, and what my blocks are (for instance, time management issues and the unconscious messages I was sending out in my dating profile). Then we thought about what goals were realistic for me to accomplish by the following week.

Having someone else provide an objective opinion, who also validated my own decisions, was immensely helpful, especially during the times I experienced rejection.

He also provided insight into the male perspective in dating, which helped me develop more empathy for my would-be suitors.

Managing weekly tasks with Trello

If dating is a numbers game, I had to go out and meet as many men as possible, despite the sweet temptations of staying in.

I use Trello, an online project management wall, to organise everything. It lays everything out into handy columns: To Do, Doing and Done.

I set up weekly sprints to get through my tasks, such as writing to five men a week, responding to the messages I received, going to at least one singles event a week, and, of course, actually going on dates.

Seeing my progress as I moved tasks to the Done list was encouraging. I felt that I was making progress.

Diversifying my portfolio

Because I'm so anxious about dating, I can overly focus on one person when I click with someone. However, my therapist advised me to go out with several people at once. For instance, when we set my weekly goals, I'd decide to go out with at least two different men during the week.

Dating many men took the pressure off any one person for me, and I was able to focus on having a good time with the person I was out with.

And since I had a pre-determined goal, I wasn't filtering out men I wouldn't normally go out with. I just needed to hit my goals.

Previously, I'd come up with any reason to not go out with a man. Maybe he was too tall, or lived too far away, or was too outdoorsy. I often put 'too' in the way of getting to a first date.

But by diversifing and going for numbers, I was meeting men I wouldn't normally consider and having a good time. I never knew it would feel so good to not date my type.

The result of my dating project

So, how's it all going? Well, after all this -- the professional photos, the spreadsheet, the project manager, the data software and the goals -- I'm still a nervous dater.

But now I'm nervous because I met someone nice and he's become my boyfriend. It's all very early, but I haven't felt this good about dating in years.

Ironically, taking a systematic, project management approach helped me open up and become confident enough to let someone in. More than anything else, that's been the biggest difference in how I approach dating.

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