How to Design Dates That Don't Suck (Part 1)
First Date Anatomy and Examples
Bad dates suck, and I hate them. I hate them so much that I’ve spent years developing and testing out templates for never having bad dates again.
Having now designed and delighted in over five hundred dates, I’m sharing my process here.
When designing a first date, focus on three key things:
1. Is this something I enjoy so much that I’d even do it alone?
There’s no rule for what a date is supposed to be, so I like to get creative and design dates that accomplish things I was already excited to do. This serves two purposes: first, it puts me in a mindset of adventure and discovery, rather than anxiety or judgment. Secondly, it ensures that even if my date gets stuck at work and has to postpone, or flakes entirely, I can treat myself to a solo date, then fill them in on what they missed and start planning what we might be able to do next.
I recently asked a lover about her approach to date design. She corroborated:
Unless someone is actively being mean or trying to harm me, I never have a bad first date. I keep it low stakes, and I pick date things that I’d want to do anyway whether or not I have another person with me. That way, I don’t need to think about sunk costs of the date, or how much labor I put into preparing for it.
2. Can this date design withstand, or even improve from, sudden shifts in weather, timing, or bodily needs?
An outdoor picnic can be ruined by rain, and a nice dinner can be ruined by a stomachache, so I try to build failsafes into each date so that when nature calls or the rain falls, the date seamlessly evolves into something even more enchanting.
The thunderstorm that hits during your hike becomes an opportunity for a rainforest safari followed by hot chocolatey snuggles under a warm blanket fort. A sudden work/family urgency becomes a mere intermission — an opportunity to regroup before the next chapter of the date gets to unfold.
After all, if dating is (at least in part) meant to simulate the attentive care and support we hope to give in a relationship, then any unforeseen challenges become tangible vignettes of how we can show up for one another in word, deed, and spirit.
3. Does this date allow for a healthy balance of shared experience and shared divulgence?
I like to think of dates as opportunities to go far and go deep. We go far by physically traversing various types of terrain, from coffee shops to forests to boardwalks to bedrooms. We go deep by unveiling honest, vulnerable parts of ourselves, and challenging one another to meet us where we’re at with compassion.
Connection lives in these spaces between us that we willingly choose to navigate together. Sensing the depth within one another will make us excited to explore further on our next date. Of course, there’s no guarantee we’ll be perfectly compatible on every dimension, but by going deep, we can quickly learn where our incompatibilities lie and confront them head-on, rather than building up false hopes and expectations over time that become more costly to confront later.
What templates/genres work best for first dates?
I’m a huge advocate for what I call chapter dates. First, you concoct a variety of things to do over the course of a day, or weekend. These are your chapters. Then, based on how you're vibing together on the date and what urgencies are on your respective radars, you can choose to continue on to the next chapter, skip ahead, or make helpful additions/modifications.
Consider a date in which you suggest playing a game of tennis together, then scrounge picnic ingredients from a nearby grocery store and go people watching in the park, followed by sunset, street tacos and live music, with the option of heading back to one of your places together for cozy vibes, playlist sharing, and yoga. You can mix and match the order based on your respective moods, and if you can’t fit it all into one day, that’s a perfect excuse for a second date!
Here are some other first date archetypes that have proven exceptional year after year:
Hikes & park strolls — great for contemplative conversation, exercise, fresh air, nature, people-watching, and appreciation of changing seasons. If you both take fun photos of one another along the way, you’ll have mementos to commemorate your first date, and you can even use those photos for future dating app profiles and potentially be partly responsible for them finding future love!
DIY adventures and quests — great for bonding and camaraderie. Some of my favorite quest ideas include picking a type of dish you both want to cook, setting a challenging budget, then grocery shopping together to see if you can procure the ingredients within your budget. It’ll teach you to work together, learn each other’s communication styles, and exercise your creativity. I’ve also tried things like scavenger hunt dates, attempting to find all the waterfalls in our city (including secret underground ones), and trying to find the highest hills, ledges, and vistas.
Crafting and/or coworking — spend your first few hours together diligently focusing on a creative project (writing, art, design, etc.), then discuss your progress over a homemade lunch. You get to learn about each other’s passions, projects, vibes, and skillsets. Even if you’re ultimately not romantically compatible, you still come away with a tangible accomplishment and the ability to refer each other to future friends, colleagues, or lovers.
Next up…
I have so much more to share on this topic! Stay tuned for more, and subscribe if you haven’t already.
Practical steps for suggesting — and designing — your first date
What typically causes a first date to fail
Overcoming sexual & romantic expectations
First date conversations
How to create space for all the people you meet to feel comfortable and excited navigating this process with you
Need help with dating, personal development, or navigating relationships? Let’s talk! I’ve been a coach and dating app consultant for nearly 15 years! Schedule a call with me and we’ll talk through your life, goals, struggles, and strategy. First call is free, and I’ll do what I can to point you in the right direction!
~Steve
This is awesome!