How to Design Unforgettable Dates (and Nail Every Single One)
Principles and tips to master Date Designing + Call for 1-on-1 virtual coffee chat
You’ll be all set to design and experience the best date of your life after you’re through with this article. Bold claim, I know, but after failing at it and embarrassing the heck out of myself for over 6 months in the latter part of 2021, I spent the next 18 months (almost) trying to get REALLY good at this. And I did pretty good at it. So, when I make bold claims, I think you might benefit from trusting me on those.
In 2022, I went on over 35 dates (each with different people). Through dating apps (yes, you can get matches there (if you don’t already)), sometimes with cold outreach (yes, it works), sometimes because we were in the same class, etc. Some of these would end up with the girl venting to her friends (I’d learn later) about how uninteresting and dull the experience was. Much later, some would end up with them rating the date as the best they’d ever been on.
My friends and colleagues would later learn of this and request me to help design theirs. While I did help them then and there, I postponed indefinitely the idea of ever publishing an essay or article about my methods. I was afraid I’d be branded as the dating guy in tech—or rather, I was afraid I’d be known ONLY for that.
Now, however, I feel like finally publishing this. I mean, why not?! I’m just a chill guy, after all…
Starting in early 2022, I began reading a lil too much on dating, seduction, courting, love, and the like (you can find all my book recommendations here). This was because I knew I lacked the courage (mostly) and the skill (partly) to talk to the girls I wanted to talk to.
With this article, I’ve laid down all the principles I’ve discovered over my time dating and studying the subject. I’ve laced them together so it’s easy to go through this long piece + come back to it when you’re planning your next date..
Now we get to the actual meat of the material. But before I start, please know that ‘designing/planning dates’ is just one little part of the entire ‘dating’ journey. There’s a lot to learn, instil, and uncover under ‘dating.’ One either learns it through trial and error themselves or has a big brother/sister to help them with it (I’m trying to be that brother).
I’ll focus solely on designing dates here.
Setting Goals
Okay, you’ve got someone ready to go on a date with you. What’s the immediate next step?
You better know what you want out of it and how you want the other person to feel about the experience.
Stages in Dating
Relationships evolve, and so do dates together with them. Your goal for the date will be different when it’s the first time you’re meeting someone, compared to when you’ve had 5 or more dates together, or when you’re actually dating (more on these phases and the outcomes you want from them later in this article).
Assuming it’s the first time you’re seeing each other on this date, here’s what your goals should be:
To conclude if you’d like to either be romantically involved with them, be just friends, or never see them again.
To grow into a more fun person yourself—become more presentable, charismatic, and secure.
To learn how to make the person who has trusted you with this date feel safe and heard.
Principle of Optimisation
Follow the general principle of optimisation, i.e., set concrete goals → optimize for that which will move you toward those goals.
Once you know what your goals are, the next step then is to figure out what to optimise for on the date. Since my goals with first dates were always the ones I’ve listed above (and I recommend the same for you too), here are the things I would optimize for:
Fun
This is me challenging myself: what can I come up with to maximise fun? This helps me sharpen my social skills and makes me a lil more charismatic. Both me and my date are more likely to look forward to further dates if we know they are easy and fun.
Robert Greene, in The Art of Seduction, writes:
The mind loves surprises. A carefully crafted experience that oscillates between excitement and relaxation keeps the other person captivated.
Familiarity + Genuine Interest
Do I know what my date is into? Her interests? Does she seem interesting? I’d want to have this date closer to her locality and in a place she knows. It’ll be easier for her to travel, and since she’s familiar with the place, she’ll feel more comfortable trusting me.
In How to Win Friends and Influence People, Dale Carnegie suggests:
Make the other person feel important—and do it sincerely. A simple acknowledgment of their feelings or interests can transform a casual interaction into a meaningful one.
In Attached, the authors explain:
When someone feels they can rely on you to respect their boundaries and needs, they begin to feel safe. Safety leads to openness, and openness fosters intimacy.
Physical Touch (Given You Want Romantic Involvement and Wish to Judge Reciprocity)
Never rush. Once you sense that it’s easy enough to talk—about yourselves, each other, or, better yet, a third object or topic—observe how comfortable you both feel with light, safe touches. For example, a light elbow touch when walking together, gently guiding her by a touch on the back, or helping with a chair. These moments help you assess whether your date sees your dynamic as platonic or if there’s subtle, mutual sexual tension.
Respect both outcomes! If you can have fun together but the equation is platonic, you might gain a really good friend in your date. If there is sexual tension, there’s room for safe escalation.
In Models, Mark Manson writes:
The key to physical escalation is not about doing something, but rather about recognizing when something feels right. Touch is not something you do to her; it’s something you share with her in a moment of mutual connection and trust.
In Attached, Amir Levine and Rachel Heller write:
Physical affection often serves as a gauge for emotional closeness. While some people thrive on touch as a way of connecting, others may require time and trust before they feel at ease.
My greatest learning is that it usually takes at least three dates to understand your date’s love languages. If you’re able to secure successive dates with the same person, you can build trust and shared ease over time, eventually escalating physical touch—even if the first dates feel a lil awkward.
Knowing Your Date
One of my greatest learnings is to always gather as much info as I can on my date’s interests (without it seeming like stalking).
Another principle I follow is to use text only for logistics and planning (before the first date) and reserve dates and IRL meetings to experience things together—not just talk (you don’t want an interview, do you?).
That said, gathering info on her interests and preferences over text before the first date is part of working out the logistics.
Before the best of my dates, I made sure I knew at least a little about:
Her preference in food
Her schedule and the time she could offer. Respecting their availability shows empathy and thoughtfulness
How nervous she might be about the date
A vague idea (since this changes too often) of what she’s looking for
Gathering such info helps design the date better, and significantly increase quality of conversation you could have. Prep is sexy.
Blind Dates and How to Handle Them
Okay, but what if I’ve never spoken to the person before? If it’s a blind date? You could argue that first meetings from dating apps are blind dates too, but I’m talking about when your date is arranged by a third party—maybe a friend, family member, or colleague—when neither of you has any prior knowledge about the other.
Here’s what to understand:
Dating is an exercise in self-discovery and growth. And it applies even more strongly to blind dates. The focus has to be on developing genuine self-esteem rather than chasing superficial validation.
Blind dates work best when you are comfortable presenting yourself as you are—with complete vulnerability and a total lack of the need for validation from your date. If you feel good about yourself, blind dates will feel good to you.
The better question to ask then becomes: How does one feel good about themselves?
How Dates Evolve + How You’d Want Them to Evolve
Above, I wrote that relationships evolve—and so do dates, in parallel and together with them. I suggest approaching all dates with an idea of what success in them would feel like for both the people involved, and what it would look like to you.
Thinking of dates as evolving through phases can help you set realistic expectations, define personal goals, and make the experience more meaningful.
Phase 1: Getting to Know Each Other (Can I Have Fun With This Person?)
During the first date and up to, at most, the third date, your goal is to figure out if you can have fun with this person and determine whether you two can get romantically involved. If the person seems interesting, has a life of their own, and there’s a sense of sexual tension (e.g., subtle flirting, lingering eye contact, or playful teasing, etc.) between the two of you, you’ll likely have answers to those questions.
If your date doesn’t seem as interesting as you’d like your romantic partner to be, isn’t fun, and there’s no budding sexual tension, you might want to reconsider going on a second date with them.
Phase 2: Okay, We Can Have Fun Together. Now What?
After the 3rd or 4th date, your dates should have matured, and there should be a sense of comfort in talking with them. By now, if you’re sure that the person you’re seeing is interesting, that there’s sexual tension between you, and you’d be down to date if all goes well, here’s what to do.
Your goal with dates now should be to:
Learn Each Other’s Love Languages
You have to communicate with people in the language they understand. In relationships, people express affection in their own unique ways—these are called love languages. Over the course of your dates, figure out your own and your partner’s love language.
Is one of you very vocal about how they feel and expects the same level of verbally expressed love and appreciation? Words of Affirmation might be their love language.
Does one of you demonstrate love through gestures, like looking for opportunities to help whenever possible? Acts of Service might be their love language.
Similarly, giving gifts, planning intentionally for quality time, and showing affection through physical touch all count as love languages.
Observe yourself and your partner. Pay attention to what they complain about, notice their actions, and watch how they react to your efforts. Once you understand their love language, love them in the way they’ll appreciate most!
Skim through Gary Chapman’s 5 Love Languages, or watch a YouTube summary of the book.
Introduce Unfamiliarity
By now, you both should feel safe in each other’s company (you must still, however, prioritize making your partner feel safe at all times).
At this point, you can gradually introduce new and unfamiliar things to keep the fun alive. Suggest places to go that you both haven’t visited or activities you’d shy away from doing alone or with others. Bouldering, a gym session together, or cycling somewhere not too close might be great ideas!
As your comfort grows, exploring mutual and individual interests can deepen your bond further.
Explore Her Interests
Attend comic shows (now I’d recommend the front row), go to concerts together, shop for clothes, or try boxing classes as a pair. Create opportunities to learn more about each other’s interests. Maybe explore something new to you but familiar to them? Trying new activities together fosters shared memories and keeps the relationship exciting.
Phase 3: We Are Dating, But It’s Never Boring
If you’ve made it this far, you’ve probably already decided to call it official. At this stage, you’d want to:
Keep Learning More About Each Other’s Interests
Relationships thrive when curiosity remains alive. Make time to explore shared hobbies or delve deeper into each other’s passions. Discovering new facets of each other helps keep the relationship dynamic and evolving.Learn How They Discuss Issues, Argue, and Resolve Problems
Understanding how your partner handles conflict is key to long-term compatibility. Pay attention to how they express disagreements and work toward resolutions. Healthy communication now lays the groundwork for a strong relationship.Solve Problems Together
Life inevitably throws challenges your way, so navigating them as a team becomes crucial. Whether it’s “How do I let my parents know?” or “I might move to a new city; how do we keep this alive?”— Solving problems as a team not only addresses practical concerns but also fosters trust and a sense of partnership
At this stage, it’s all about deepening your connection while navigating life’s complexities together.
Pro Tips
Be Interested, Not Interesting
As much as dating is an exercise in self-development and discovery, please don’t be a jerk and make it all about yourself. It’s cool that you’ve achieved a lot, that the problem you’re solving at work is fascinating, and that your new PS5 is actually sick. But keep all that aside and listen. Better yet, dig deep. Try to learn as much as possible about your partner—without being obnoxious.
Cliché, But Think Positive
Last year, I got rated 10/10 on a date. My date even said it was the best one she’d ever been on. Before I left my apartment that day, here’s what I wrote in my Notion journal:
Visualize It Ahead
Think about how the date will flow, and what experiences might make it memorable for both of you. What does success look like? How should you both feel afterward?
Find Something to Judge Together
The best dates involve both of you judging a third thing together. This is why art exhibitions are such a great idea—you can either appreciate the art or wonder why you can’t see what’s so good about it. The point is, you do it together. When judging something as a team, the burden of appearing agreeable or perfect disappears, and things flow naturally.
Enter the Date In Media Res
In Models, Mark Manson writes:
Most people start conversations or dates with boring, predictable pleasantries: ‘How was your day?’ or ‘So what do you do for work?’ While these questions aren’t inherently bad, they don’t create an emotional spark or intrigue. Instead, you want to start the interaction in medias res—right in the middle of something interesting or exciting. This could be a fascinating observation, a playful comment, or even a personal story that invites the other person into your world immediately.
A personal opening that worked for me:
“Do you think this place has the best coffee in CP, or is it just hyped up?”
Eye Contact Is Good, When It’s Not Too Much
Eye contact is GREAT—when it happens naturally. It’s creepy if it’s forced. General rule: Eye contact lasting over 3 seconds without preexisting sexual tension is super uncomfortable.
Request to Limit Phone Use
“Hey, how do you feel about putting our phones out of sight for a couple of hours?”
Smell Nice
I highly recommend this set. Also, learn about what perfumes to wear and when to wear them!
Look Up Games to Play Together
“Whoever pets the most dogs today gets a treat!”
“See that person over there? Come up with a backstory for their day.”
These games help build shared memories. I’ve got tons more of these. If you’re planning a date soon—maybe get in touch? (Read how to below!)
Reflect When You’re Back Home
Take like 10 minutes to think about the date you just experienced. Did it answer the questions we wanted clarity on? Reflecting on what went well and what could improve helps you grow and prepare for future dates.
It’s Okay If It Didn’t Go Right—Dating Is a Process of Elimination
Rejection is often not about you; it’s about compatibility. Trying to avoid rejection leads to a life of pretending to be something you’re not.
Rejection is the process that filters out people who aren’t compatible with you. Move on.
Note + Closing Thoughts
Okay, this was a particularly long article. It was (obviously) not exhaustive, though. It keeps evolving, and I keep learning—just like you. If you think you have something to add or have related questions, use the comment section to let me know. I have strong opinions, but they’re loosely held.
I am no guru. And PLEASE don’t brand me as one. This was just an attempt to share what I’ve learned over the years. I try to approach things principle-ly, and I believe what helped me will help you too. That said, I know everyone and their situations are different. It’s all very subjective. If you feel stuck, read my material or the books I recommend.
Finally, if you’re too lazy—or simply smart—why go through all the books when I already have? I’d be happy to speak 1-on-1! If you’re planning a date, seeing someone, or just don’t know how to get started, get in touch using the button below.
I’m building FTS (Fuck The Spark), the most unique dating community that actually gets results for you—helping you design better dates right now for FREE!
