Approaching my mid-30s, I started thinking about what I really wanted from life. I’d spent the last decade prioritizing learning & exploration, and with my now awareness that life is very finite, my strongest desire transitioned to creating a meaningful & abundant life.

In my typical type-A style (it’s both my green and red flag), I built a 6 month roadmap to tackle dating. The process has been frustrating, fun, and also intellectual catnip for a nerd like me.

Here’s what worked for me, plus the story of how I got banned from Bumble.

What worked: Getting clear on why

Dating apps exist to facilitate “connection”, but that can mean anything from no-strings-attached hookups to building a family. Psychologically, some people are looking for a solution to loneliness, some to feel desired and alive, others a solution to boredom, while some are looking for meaning.

To get what you want, it’s important to get clear on what that is and announce yourself as quickly as possible. Before I started, I wrote the following in my journal:

Really, I’m looking for a life co-founder. Important qualities:

Capable & courageous.
Sunny & optimistic attitude (most of the time).
Good person: cares about the world, community, each other. Acts with integrity. Not perfect, but willing to be humble, work with ego, try to do better.
Likes to play. Wants an abundant life of joy.
Wants impact, or understands the desire for impact.

Looking back, it’s interesting how often I’ve shared these specs – it resonates strongly with people who are looking for the same things, and quickly identifies mismatches.

What worked: Go on 30 first dates

A lot of people see dating as hopeless and impossible. I once heard someone say, “I want a family, but one does not simply walk into Mordor.”

This is just the cold start problem. The solution: walk into Mordor.

More practically, set yourself a numerical target. Go on 30 first dates.

It doesn’t matter if they’re not your type, or have totally different interests. In the beginning, as long as they pass some basic filter of “probably not dangerous and we could be friends,” just go.

Action leads to results. And you can adjust tactics later.

This approach was particularly effective for me because I’m someone who likes hitting KPIs. Even if a date wasn’t great, I’d still get the reward of “leading indicators are looking good” and continue to feel motivated.

What worked: Dating as self-awareness

But acting like a metric-focused robot isn’t a great way to build human connection.

The attitude I’ve found helpful is to approach dating like a radical practice of self-awareness. In every interaction, aim to learn something about myself and aim to learn something about someone else.

Dating is a rare opportunity to talk to a variety of people about what they most want from life. What struck me most was how vulnerable dating is for everyone, and how we’re all still figuring out what we actually need.

Things other people have shared:

“Having children is life changing. When your kid does something great, it’s like seeing your team win, but 100X.”
“My work is my calling, and I’m not willing to let a relationship or kids get in the way.”
“I’m not the super ambitious & driven type, it’s most important to me that my partner accepts me for who I am and doesn’t make me feel inadequate.”
“I have a strong preference for dating other founders. I know I definitely don’t want a trophy wife, I want an actual life partner.”
“I’m pretty relaxed and kind of type B, so I don’t do well with people who are more intense.”
“My ex and I had different lifestyle and level of drive. I couldn’t imagine raising kids together.”
“There isn’t anything wrong with my ex. We didn’t have the right communication tools.”

I’ve learned about myself:

Polyamory is not for me. It seems to work well for some people when implemented ethically, but it’s messy and requires a lot of extra effort, which isn’t compatible with my top priorities.
I think I do want kids. While it’s not a requirement to live a good & fulfilling life, with the right partner and an intentional plan, it’s almost certainly a beautiful source of meaning.

That time I got banned from Bumble

At about 4 months in, I was no longer a “new” Hinge user, so I decided to switch over to Bumble. I felt like I had gotten the hang of things enough to start running a more efficient process.

Three weeks in, things were going great. I had already gone on two first dates (both enjoyable and friendly) and had two more scheduled. I was logging in to confirm a time when I got a blank screen:

“Your account has been blocked because we’ve received several reports about your behavior on the platform.”

When I followed up with support, I received another automated message,

“We’ve decided to block your account for violating our Commercial and Promotional Activity Policy.”

There was no chance of further human review. A 3-month subscription to Bumble costs ~$250, but a lifetime subscription costs only $300. This meant they were resigned to members churning in 4 months. With an LTV of $300, there is no margin to support a human review team.

I’m a product person, so these baffling messages sent me down a rabbit hole of reverse engineering what happened and why.

What I did to trigger multiple reports

A close friend who met his wife on Tinder told me he almost swiped left on her because she didn’t write anything on her profile. He told me, “that’s the problem isn’t it? The terrible profile could be your soulmate. You have to keep playing the numbers game.”

I decided to cast a wide net. It didn’t feel like it would be a big deal to filter out later.

And so, I started chatting with many different types of people. When I identified a significant value or lifestyle misalignment, I quickly unmatched.

Unlike other dating platforms, Bumble explicitly lets users know they’ve been unmatched, and gives them the option to report you even after the conversation has ended.

Bumble explains:

…being unmatched after a good chat or a date is different. We know this can hurt, which is why we introduced our Unmatched feature.

…The Bumble community told us that being able to see when they’d been unmatched gave some welcome closure to a sometimes unpleasant experience, and helped them to go find someone better suited.

This product decision makes some sense – it’s extremely important for Bumble to protect their member user experience from destruction by callous users. (It causes “dating burnout” and probably has a huge impact on churn.)

But the problem is that people vary in their reaction to “rejection,” no matter how slight. People disagree about what constitutes a “good chat” as well as what level of “closure” they are owed.

In my 3 weeks on Bumble, I probably unmatched around 20 people. Given how brief these interactions were, I didn’t feel the need to soften things or explain myself. A small proportion must have used the Unmatched feature to report me.

What I did to trigger the Commercial and Promotional Activity Policy

I’m not the first person to build a funnel process or view dating as an analytical problem. John Gottman famously met his wife Julie on his 60th first date in 1986. The OkCupid era of the 2010s kicked off a trend of people (mostly male mathematicians) successfully gaming the platform to find love, though women too have applied transferable skills from performance marketing.

As long as internet dating has existed, so have scams and catfishes. But the process has always been fairly manual, and therefore limited. Even the Tinder Swindler is estimated to have had only about a dozen victims from whom he defrauded around $10 million.

But today, the process has gone industrial. From OnlyFans agencies hiring workers to chat on behalf of girls with millions of subscribers, to AI systems that can bypass even the need for workers, “connection” or at least early dating engagement is now easy to scale.

This means that fraud detection is likely now a huge problem for Bumble.

To be clear, I didn’t hire offshore workers or build an AI chatbot. Even to me, that feels weird, like crossing a line. But, I did try to maximize perceived engagement while minimizing cognitive effort when chatting with strangers.

A lot of people struggle with creative conversations, and so Bumble helps by providing a list of pre-defined icebreakers. I noticed that most people chose the same openers, and conversations tended to go down a few very similar paths.

To increase efficiency, I wrote a few high-engagement responses to frequently repeated questions and started copy-pasting them. For example:

Ice breaker: What job did you want when you were a kid, and why?
Answer: Astronaut! It was the 90s version of being a ship captain who gets to explore the world.

Question: How’s your weekend going? Do anything fun?
Answer: Thanks for asking, it was nice! My weekends follow a pretty predictable routine. I teach yoga Saturday mornings, and I just came back from a fun BJJ open mat and am now winding down a bit. How about you?

Ironically, because I took the time to write long and thoughtful responses, the consistent quality and exact repetition made it more obvious to NLP algorithms that I was using automation. To Bumble, I looked like a bot running some sort of commercial operation, not a human trying to conserve her energy.

Distinguishing creative but lazy humans from actual bots at scale is a hard Trust & Safety problem. But given Bumble’s LTV and business model, it may not even be worth solving.

Which brings me to product design at dating apps.

How to “game” modern dating apps

It’s common for people to try to hack app algorithms with counterproductive behaviors:

1. Spray and pray. Swipe right on everyone to see who sticks, then unmatch people you weren’t actually interested in.

This creates terrible UX for other users, so algorithms quickly blacklist these accounts.

2. Throw a tantrum. Reject everyone in your queue to tell the algorithm no one is attractive enough for you.

This likely flags you as someone with an ornery attitude who won’t engage positively with other users, so the algorithm lowers your visibility.

Though it was frustrating for me, maybe it made sense for Bumble to ban me. In 2025, we are past the era of funnel hacking.

After all, the actual value of finding a life partner is well above Bumble’s LTV of $300. A dating platform is a community where the “product” is consistent, positive interactions with other members. A user who degrades UX for other people is bad for business.

Dating apps have to be designed to reward pro-social behaviors. The smart way to increase visibility via the algorithm is to match your behaviors with platform incentives:

1. Slow down. Focus on fewer, better connections.

Hinge caps active matches at 8, but the sweet spot is probably lower. Platforms want sustained engagement, not users who burn through their entire user base quickly.

2. Practice good citizenship. Send thoughtful messages, actually schedule dates, and be genuinely enjoyable company even if there’s no romantic fit.

When you show up like this, it keeps other users active and subscribed, so the algorithm rewards you with better visibility. When Hinge asks “Would you like to meet more people like X?” make sure your dates consistently respond yes.

What’s working: Living life off the apps

Maybe this story is about how the product designers from these dating platforms successfully nudged me to date less like a robot and more like a human. I’ve learned that finding a life partner isn’t something I can product-manage my way to a quick solution. I can enjoy the process and not be subsumed by it. So far that has been valuable.

I recently chatted with Lauren Hauser, a dating coach on Logan Ury’s team. After our conversation, she wrote me:

One reflection I had was that it reads to me that you’re at a natural pivot point. You’ve grown more discerning – clearer on what matters: shared values, coherence, a life co-founder. And you’re right, that resonance you desire may feel a bit rarer.

I can imagine that what you might want to orient to isn’t more effort – but a new rhythm and some pattern shifts to re-engage. One that feels easeful, spacious, and self-honoring. Not about doing less, but doing it differently.

I think that’s excellent advice. For now, that means not being so active on apps. (Though I think a new app called Sitch is really innovating on product, so I’m trying it out.) I’m staying open but also living my life and letting myself spend the time I want on other interests.

Also, as of today, I’m still on the market. If you know anyone great, feel free to send them my way!

Tags: Product, Personal