Agile Dating - A Less Painful Way to Date

How relationship experiments helped me find the love of my life

This has been one of my most requested topics to write about. I hope you enjoy it! If you think it might be helpful to others, feel free to share.

When my seven-year relationship ended, I was unceremoniously thrown into the chaos of online dating. I was an introvert and busy professional in my late 20s. This was the last place I wanted to be. Yet I knew that if I were ever to find my life partner, I needed to bravely venture forth. Fast forward six years, countless dates, and several relationships - I’m about to marry the love of my life.

Looking back, it was not an easy journey. Searching for “the one” was like dancing blindfolded in a field of ambiguity and pitfalls. But what made it far less soul-crushing, more humane, and efficient was an approach that I call Agile Dating.

Modern dating is weird.

We sift through an open market of strangers, attempting to suss out who might be a life partner with limited information and time. I found this process to be uncomfortably confusing and stressful. So many questions swirled in my head when I matched with someone new, like…

• What are this person’s needs and expectations, and how do I communicate mine?

  • Constantly having to navigate new sets of unspoken rules, boundaries, and desires was emotionally exhausting. One guy tried to kiss me after a first date and I gently pulled away. I was still interested in him, but wasn’t ready for physical intimacy. He must have interpreted this as rejection since I never heard from him after.

• How long do we date each other before we decide if we should move on?

  • It often takes time to get to know someone and for romance to blossom. However, investing time in one person meant that I had less capacity to meet others. It was hard to know how long was long enough to give a relationship a chance.

• How good is good enough?

  • I didn’t yet know what my “minimum partner requirements” were. I was afraid of settling for a mediocre relationship, but I also didn’t want to have unrealistic expectations and be searching forever. 

• What if I lose “the one” because of something easily fixable?

  • I didn’t want to end up in Pride and Prejudice-like drama and lose “the one” because of a silly misunderstanding. I was once disappointed that a new partner didn’t take interest in any of the art and books at my place. I interpreted this as his lack of interest in me personally. Turns out, privacy was important to him and he was trying to respect mine. After a simple conversation, we both made some easy changes in our behaviour and expectations. 

All these questions and more had me overwhelmed with self-doubt and anxiety. I longed for transparency, clarity, and better communication. I sensed that my partners did too.

How to navigate relationship uncertainty?

As a designer, I realized that I already had helpful methods for navigating uncertainty - design thinking and agile methodology! When exploring new ideas, designers begin by interviewing users to understand who they are and what they need. We then create a prototype of an idea to test. Based on user feedback, we reflect on how to improve our idea or we try something different. This process sets us up for the best chance of success, and allows us to experiment our way forward when there are many unknowns.

I thought to myself, “What if we approached our new relationships in a similar way?” And thus, Agile Dating was born!

New relationships as experiments

Agile Dating is first and foremost a mindset that helps us navigate new relationships with more clarity, empathy, and ease. The core principles are:

1. We approach our new relationship as an experiment.

   • Experiments invite curiosity and playfulness. We hope for the best but don’t get attached to the outcome. Each “failure” is a learning opportunity.

2. As partners, we are both co-creators.

   • We are a team in this experiment, doing our best to set it up for success.

3. We commit to radical transparency and empathy.

   • We strive to express who we truly are and what we need, honouring ourselves and each other. 

4. We commit to continuous improvement.

   • We learn from our experience and feel empowered to make changes. We focus on increasing our self-awareness and acting on new insights.

In embarking on Agile Dating with someone, we are saying to each other: “I want to find the right partner. You want to find the right partner. Maybe we’re a good match, maybe we’re not. Let’s prototype this relationship and see how it goes. If we’re not a good match, that’s okay. I won’t take it personally, we just have different needs. If we are a good match, that’s great. Let’s continuously learn how to strengthen this relationship.”

My experience: This mindset helped me reframe dating from a stressful test to a creative act. It helped my partners and I become collaborators and avoid feelings of victimhood. It also helped us gracefully end our relationship without surprise or hurt egos. Many past partners are still in my life as friends now.

What Agile Dating looks like

I suggest starting the Agile Dating process once you and your partner feel chemistry and potential. For me, this was usually after one or two dates.

Each Agile Dating experiment is called a Sprint, beginning with a Kick-off and ending with a Check-in. I found that two weeks was a good length for a Sprint - just long enough to get a decent sense of a partner.

You can be as structured or casual with the Agile Dating process as you’d both like. Some of my partners loved the idea and we even drew things out on whiteboards. With other partners, we just loosely followed the process.

1. The Kick-off

The goal of the Kick-off is to set you and your partner up for success and avoid preventable friction during your Sprint. This is dedicated time to get to know each other at a deeper level, find out what your needs and expectations are, and begin your experiment with trust, clarity, and excitement. 

My experience: As someone who’s monogamous, I was nervous when I began dating someone who was non-monogamous. Our Kick-off helped us get clear on what we both needed to enjoy our relationship without worry. My partner shared who else he was seeing and the nature of their relationship. I shared what I needed from him to feel prioritized and cared for. We agreed that it was important to call each other regularly. Knowing we were on the same page helped me feel at ease about what I was stepping into.

Suggested agenda:

• Schedule one hour for your kick-off. Find a place that’s private and comfortable.

• Share and discuss your answers to the following questions:

  • What are your hopes for the relationship?

  • What are helpful things for your partner to know about you? (eg. your likes, dislikes, quirks, routine, love language, attachment styles, personality type, comfort level around physical intimacy, etc)

  • What might you be concerned about? (eg. dealbreakers, challenges, past experiences, etc)

  • How would you like to communicate with each other? (eg. frequent calls, minimal texts, etc)

  • What agreements would you like to make to help you both feel excited about your Sprint?

• Schedule a one hour Check-in two weeks away.

2. The Sprint

During your next two-week experiment, your goal is to fully experience what unfolds between you and your partner. 

Check-in with yourself regularly - how does your partner make you feel in your mind, body, and heart? What might be behind these feelings? It may help to journal as things come up for you.

3. The Check-in

The goal of the Check-in is to reflect on what you and your partner learned from your experience together and decide what your next steps are. You may want to embark on another Sprint together, or you may wish to end the experiment.

At the Check-in, both of you should be ready to share and receive honest reflections. It’s important to acknowledge that all your experiences are valid. Different learnings may arise - a need you didn’t realize you had, ideas for how to show up better for your partner, or a recognition that you aren’t the right match for each other. Be gentle, kind, and open to what emerges in this space. 

My experience: I had been dating someone for several months. It wasn’t perfect, but I enjoyed our time together and thought we had potential. At our next Check-in, my partner shared that he didn’t feel we were a long-term match. Although I was sad to hear this, I was prepared and grateful for his honesty. We agreed to end our romantic relationship and transition into friends. We even became each other’s cheerleaders as we looked for new partners. A few months later, I met the person who is now my fiancé.

Suggested agenda:

• Find a place that’s private and comfortable.

• Share and discuss your answers:

  • What did you appreciate about each other during the sprint?

  • What could have made it even better? (I recommend using the Non-violent Communication Framework)

  • What did you learn about yourself? (eg. new needs, boundaries, fears?)

• Share and discuss your answer:

  • Would you like to end the experiment, or would you like to continue for another Sprint?

• If both of you decide to continue for another Sprint:

  • Is there anything you’d like to do differently in your next Sprint?

• If both of you decide to end the experiment:

  • Would you like to transition this into a different type of relationship? (eg. continue to be friends? Don’t keep in touch?)

  • Thank each other for trying out the experiment together and wish each other luck with the next one.

4. (If applicable) Continue to the next Sprint

Repeat parts 2 and 3. Feel free to adjust the length of your Sprints. If you feel that bi-weekly Sprints are too short, you can try monthly. If they’re too long, change it to weekly. You may also want to adapt the questions to what works best for you and your partner.

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Common Question: How do I bring up Agile Dating with my partner?

The following conversation starter worked well for me (feel free to customize): “I’m really enjoying our time together and would love to see where this goes. I wonder, would you like to prototype a relationship together?” My partner would usually be intrigued by this and ask me to say more. “We could try an experiment where we date for 2 weeks, then have a check-in at the end to see how we felt about it. If either of us don’t feel we’re a good fit, that’s totally okay and we can end the experiment. But if we both had a good time, we can decide to keep the experiment going. What do you think?”

Keep it light and playful. Be open to suggestions from your partner. Again, you can be as casual or structured with the Agile Dating process as you like. Adapt it to your unique situation and comfort level.

It might also help to share this post with your partner.

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And that’s it! 

If you’re fortunate, one of your relationship experiments may turn into a long-term one like it did for me. Even two years in with my fiancé, we continue to use the Agile Dating approach. Our experiments now focus on how we can better support each other and make our relationship more resilient.

Stay tuned through this newsletter for future posts on:

• How my fiancé and I apply Agile Dating to our long-term relationship

• How I’ve been applying this approach to cultivate stronger friendships (Agile Friendships)

• How I got to know and express my needs better, in preparation for successful Kick-offs and Check-ins

  • My book Finding Your Authentic Self: An Illustrated Journey to Well-being includes guided reflections to help with this.

I know that it’s not easy to find a life partner. The journey can be long and demotivating at times. I hope that Agile Dating can help you and your partners find more ease, clarity, and joy in the process.

Wishing you the best on your dating journey! Let me know how your relationship experiments go!

One of my happiest days ❤️

If you have questions about Agile Dating, feel free to post in the comments or join an upcoming community call (I’ll announce them in this newsletter). I also offer coaching to individuals and couples who’d like the support (more info).

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❤️ A heartfelt thank you to everyone who gave me generous feedback on this post, making it more clear and helpful. Chris Coffman, Eliezer Abate, Drake Greene, Leslie Myint, Kola 🔑 , Justin Nothling, Alon Gilboa, Nicole Husain, Nata Kostenko, Luwam Asghedom, David Wolever, Karina Sengupta, Carly Valancy, Leo Ariel, Emma Cheung, Nate Gerber, Ashley Moon, Eric Boyd, Caleb Rudnick, Liza Futerman, and the Awaking Octopus community.

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My new book: Finding Your Authentic Self: An Illustrated Journey to Well-being

A philosophical picture book for adults. A gentle guide for a more radiant existence.

Thank you to everyone who’s ordered a copy and left a review. Your support means a lot to me and helps the book reach even more people.