the project management approach to dating

how to build meaningful connection while maintaining an intentional and healthy partnership

We’re living in a society where dating culture is spoiled with the growth of dating apps—where the pool is crowded but fishes are rare—where “What are we” becomes a question that most people refuse to answer during the dating dynamic.

If I could have one rational view about great romantic relationship, ideally it is to form a partnership that not only make you feel loved, yet also have positive impact in how you thrive in life. Throwing yourself into a relationship practice is to learn to collaborate functionally with another human being, whom you are not sure yet if you want to spend your next 6 months, 1 year, 5 years or the rest of your life with. With the limitless possibilities of life, the one you feel happily “end up with” could also become one that breaks you open.

And then what?

You transform to the new version of yourself post the relationship. Would you be wiser and more knowledgable about how a great relationship works—or would you be more vulnerable and have lower self-esteem after walking out of that so-called situationship? Would you learn more about your Why behind the act of seeking for a partner? You’re responsible for the version you aim to create.

If you keen on the philosophy of living life intentionally, you wouldn’t want to let learnings in relationship go to waste. When doing projects at work or personally, you don’t fall into projects and see how it goes like you fall in love (like what you usually see in those coming-of-age movies on Netflix). You are either assigned to work on a project or choose to do it, for that matter. The first time you receive (or pick) the project, that is when you want to get an overview of all the resources and information involved in such project, then you set the objectives, timeline and other checklist or framework for relevant stakeholders to follow through.

Working on a relationship is similar. Love to you can feel like play, but relationship needs work to function in its best possible way.

What if we view relationship building as an exciting project to do with someone we’d love to share our life with?

How to project-manage a relationship

This is not the casual, lazy and low-effort dating style.

This is also not for pure manifestation without taking any actions building the things that you say you want.

This is not the If he wanted to, he would version you see on relationship gurus’ Instagram reels.

This is a mindful, functional practice towards relationship building, for ones who seek to develop a healthy partnership, even with those who you’re not sure that you’d end up being with them for the rest of your life.

#1 Setting the Framework

If you’re dating just for the sake of dating, then this part is not for you. If you only want to put effort once you “seal the deal”, when you put a label on commitment between you and your potential partner, then you will not buy what I’m about to say.

Any project starts with an objective. Be it cultivating new initiatives, accelerating growth or maintaining what’s been working. A relationship starts with knowing what you want to do with the other person while you’re seeing each other. Or not knowing, yet at least set an intention towards the relationship. This is to make sure a person with casual dating won’t mess up with one who seeks for serious relationship and someone to grow old with. Even if there is in-between mis-match, both parties should be able to sit down and discuss how could them pivot the dynamic of the relationship in a way that suits both's needs, or consider that the relationship coming to an end.

Guys, it’s better to figure this out as quick as you agree to go on a casual date. The sooner you find yourself agree / disagree on these things, the more time you save not going through probation period with the wrong person. In fact, you might want to forget the number of dates theory someone tell you on the Internet that you cannot ask this on your first, second, third… date. Because there’s a possibility the questions you’re meaning to ask them, ended up being the reason why you guys could not move forward.

So, important questions to ask upfront when you start dating someone new:

• Objectives and intention establishment: Are you dating out of your family urge for you to get married, simply having the need to meet new people, or seriously looking for a potential life partner to do long-term life design with?

• Exclusivity parameters: How do we handle other dating opportunities? What should we do if I/you suddenly have feelings for someone else? What counts as cheating (i.e. one might say texting when the other only consider if there’s physical interaction involved)

• Social integration planning: When do we introduce each other to others in one’s life? Considering different approaches for different stakeholders like close friends, colleagues, acquaintance, etc if applicable. And how we’d like to handle such contexts.

• Exit strategy: What does one consider as worst case scenario? How do we want to handle our breakup (if this does not work out… 😔)

Prioritize tough asks over your easy-going autopilot assumption, even if you feel weird doing so. Clarify whenever possible, don’t let your instinct go to waste whenever you feel an ick inside your stomach. Also, better not let hormones speak for you when you first dating. Here is why.

#2 Iterative Development

Usually a project comes with an expiry date—that is when you consolidate what had happened into reports and meet with relevant stakeholders to review the outcome of the whole project. But when it comes to relationship building, you’re constantly moving forward with the progress of the relationship itself. Like building a product. Good product needs continuous iterative cycles, pivot changes when needed and retrospective look back on how to make it better the next phase.

Especially for the getting-to-know-each-other phase, it’s a good practice to sit down for mini reviews whether your individual and relationship goals still align—and that you still want to keep putting effort in growing this partnership.

The intention you set at first might have changed, for whatever reasons: one’s life suddenly turns into some strange transition (from unwelcoming situations like being laid-off, going through unemployment, dealing with debt,… to pleasant surprises such as getting a huge scholarship to finally go study abroad, relocating to a dream country with full support and fund from the company,…); or simply you don’t feel as attracted to them as the week before that.

Image credit goes to Rowena Tsai

Realistically speaking, I would recommend me and my next partner to do frequent relationship reviews—not only to celebrate our progress, adapt and evolve the relationship based on constructive feedback but also to plan for the milestones we both love to experience next. To sum up, below are some potential approaches for you to try with your person:

• Review and retrospective cycles: Set period/stage/sprint for regular check-ins to ensure alignment and plan next steps. Share what went well, what could be improved, and what you think would make the relationship better.

• Milestone settings:

  • Social context milestones - How you function together with others: when meeting friends, participating in events, going on double-dates,…

  • Intimacy milestones - How you connect emotionally and physically: growing levels of intimacy, expressing love / affection, trying one’s sexual preferences,…

  • Explorative milestones - How you experience new things and challenges together: doing physical activities like trekking, running,…; co-working and brainstorming; traveling,…

  • Commitment milestones - How you integrate your lives practically: defining frequency of meetups, when to move in,…

• Measurement: Focus on contribution one’s made in the relationship rather than simply look at their title or role. This means to be appreciative of your partner’s effort in meeting your needs instead of judging them based on how you label them as your personal coach, occasional therapist, career advisor or financial expert 🙏

These are what it takes to bring your “Are we on the same page?” question to the next level of awareness and clarity, which serve as checkpoints for compatibility level evaluation and development. Doing this intentionally also helps you incorporate the relationship into your life better and slowly turns the disruption of your date suddenly coming to your life into involvement and co-partnership.

At the end of the day, the goal is to support each other answer this critical question:

How can I help the other person see and decide if I'm the right fit to their life direction? :-)

#3 Communication Architecture

Many relationships fail due to the unspoken / unmet needs of either one or both parties. This comes from so many reasons including but not limited to childhood trauma, conflict in attachment styles, ego, or sometimes solely poor communication. There’re various techniques and frameworks to help you communicate better with your partner—but it wouldn’t help if you’re the only one who’s doing the real-life assignment.

You can research all the foundational knowledge and read those non-violent communication, active listening, love languages, etc for that matter. But if there’s one thing to remember and probably the easiest to act on, it is to follow up the other person with this question:

Do you want me to just listen, do you want questions, or do you want advice?

This is by far the simple yet most powerful question that can save hours of debating or unintentionally hurt each other by giving the wrong offer. If your partner is going through intense emotions and can’t seem to process the question above, try this one: In what way can I help make you feel better? When talking is not helpful, pivot the approach to something else (nicer with consent). This is when communication can be delivered via a good hug, a moment of silent or a silly joke out of distraction. You name it.

In summary, sit down with your partner and discuss what protocol and practices would best serve your needs. Or simply try and iterate (back to the #2 section):

• Questions for need clarification:

  • "Do you need comfort, advice, or questions to help clarify?"

  • "In what way can I help make you feel better?"

• Other communication practices:

  • Do energy level check-ins (0-10 scale) at the beginning of a meetup / conversation. Give the other person heads up if they’re about to hear something not so pleasant (there’s a chance they might just been through a hard day). I love how this simple check-in can ground us immediately when we pause a bit and listen to our body / mind before we rant about our days or talk about anything else.

  • Have INFORM protocol for plan changes (especially last minute) with initiative to propose adjustments if you’re the one who cannot make it.

  • Use healthy expression of unmet needs without inducing guilt. Instead of “Why don’t you do X?”, try “Hey I would feel Y if you do X, but I totally understand if you cannot do it at the moment or want to propose something else”.

  • Listen to your gut and be brave enough to tell the other person "I'm hurt when you do this" 😔 and explain your observation while allowing them to absorb before taking the blaming approach.

  • Figure out if you guys prefer permission or forgiveness approach to freedom of expression.

• Conversation success factors: It’s even better if you’re aware of your measurement in term of satisfaction level over a discussion, whether it is to serve any goal/purpose/objective or purely to enhance connection and comprehension between the two. By that it’s easier to pick the most suitable approach.

#4 Experience Design

Just like good product comes with good user experience design—if dating is a project, then your experiences together are the actual product you’re building. While Communication Architecture sets up how you talk, Experience Design is about what you actually do together.

It's easy to get caught in the trap of autopilot dating—dinner, movie, repeat—but intentional couples craft experiences that test compatibility, build connection, and yes, create those "moments" everyone talks about. But it’s not just about grand gesture or Instagrammable dates. It’s the small and consistent interactions, the mundane Wednesdays that reveal more about your potential future with that person. So how do we design experiences that actually serve the relationship's development rather than just filling time together?

• Build positive habit system:

  • Try daily ritual when you tell each other highlights and lowlights at the end of the day. Add in emotion check-ins where possible. (You can add How We Feel and Rose, Thorn, Bud as your relationship companions)

  • Practice mindfulness by expressing gratitude and appreciation. What’s one thing you’re grateful about your current partner? What are some of the things that make you feel most grateful in your life right now?

  • Be active together: take a walk, go to the gym, join a run club, whatever you both enjoy.

  • Enjoy deep, silent moments (1-5 minutes) together.

• Create small surprises with big impact: Leaving notes at one's place. Send someone a love email. Set up a date via Google Calendar with a customized description. Buy flowers just because. Do surprise visits (with consideration for privacy / spontaneity preferences if possible). These things add a subtle romantic layer to the relationship, while showing your care and attention to the other person. You never know how a small thoughtful act could lighten up someone’s day immediately 🥳

• Add some other connection practices: DIY the approach you find as the best way to connect with your partner. Back then I usually love just sitting on the couch and gaze at my former date’s eyes for 10 minutes straight without saying anything. Who would think sustained eye contact could feel so impactful? Besides, consider to add laughter and banter, or other physical intimacy languages to let you both connect in a deeper level, while showing your most authentic self.

• Bonus—Documentation: This might sound weird, but another good practice to have is to document your learnings and capture highlights from deep conversations with your partner. (Would make a lot more sense if you also enjoy putting those learnings into your blog, like what I’m currently doing)

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The ROI of intentional dating

Even if you get to witness a relationship coming to an end, the progress you’ve made and the impact you have created remain as intangible benefits. It’s an honor to the relationship you have with yourself, and who you’ve become through the whole process.

Choosing an intentional approach to dating and relationship building means choosing to be someone you’d love to spend your life with—and commit to the role model that you’ve always dreamed of.

You learn to communicate better, to recognize your own needs, and to contribute meaningfully to another person's growth. When you decide to build a relationship with someone, remember both parties are responsible for a healthy and intentional partnership—just like different stakeholders holding impact to the success of a crucial project. So, write down your intention, draw your own framework, design the experiences that you and your partner wish to have.

Own the relationship like it’s one of the most critical projects of your life.

Let’s aim to have more thoughtful partnerships, as part of us becoming the best version of ourselves, for whatever time we have together. Keep building. Keep loving.

With clarity and love,

Han x

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Bài viết thuộc thử thách Viết Tiếp Sức mùa 3.

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