I’ve quit modern romance

Let me explain...

Buckle up. This is a 15-20 minute read.

Note: This article is a product of listening to 30+ podcasts, watching 40+ YouTube videos, countless discussions with multiple friends and 1 year of reflection about patterns after being in 3 long term relationships over the last 10 years.

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So.

After 3 long term relationships across ~10 years, I’m calling it quits.

I’m exaggerating, but you get the point…

I’m not saying I’m deciding to be single for the rest of my life or pursuing a vow of celibacy.

But what’s becoming more undeniably clear is that the way I’ve been doing romance has not been working.

Of course “working” is totally subjective.

So this is what I mean by “working”:

• The mutual enjoyment of the relationship is relatively high and stable, on average

• Conflict doesn’t feel like more than 20% of the relationship (per John Gottman)

• Both parties generally feel content with how their SO shows up in the relationship

• Both parties feel like they are able to be full individuals while being in the relationship

In all 3 of my last relationships, none of these 4 things felt true by the end of the relationship despite both people putting a ton of effort in.

Oof.

Here’s what I think have been the biggest contributing variables in my 3 LTR’s “not working”:

1. The way modern relationships start create unsustainable expectations

2. I’ve failed to be honest, forthright, and communicate

3. I’ve done a poor job of evaluating for compatibility

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1. The way modern relationships start create unsustainable expectations

This seems to happen every time:

Mutual Interest —> Emotional/Physical Chemistry —> Commitment —> Honeymoon —> Compatibility Clashes —> Slow decline until break up

I’m beginning to think a big issue is the stuff BEFORE the commitment phase.

Here’s something I’ve noticed:

When I’m initially interested in someone, when we’re both talking, when there seems to be mutual interest, and sparks are beginning to fly… I change.

During this phase, I notice I become 20-40% more:

• Interested

• Intentional

• Engaged

• Playful

• Affirming

• Emotionally vulnerable

• Proactive in creating ways to connect and know each other more

A graphic, illustrated by yours truly:

Now, none of this is “bad” in of itself.

But the biggest issue is that this 20-40% increase is fundamentally unsustainable. I simply can’t continue doing those things in the long run.

It’s kind of like staying up super late to finish up an important work project.
It’s not meant to be the norm.

And if you do it too frequently, you’ll eventually crash and burn.

Of course, my SO’s never knew that I was putting in this kind of “overtime.” So my behavior just created a baseline of expectations that was setting me up for failure.

See in red, her expectations:

Initially, I’m ok, actually excited to talk everyday.
I’m enthusiastic about spending a whole day together.
I don’t mind making some sacrifices with work and other friendships in favor of the budding connection.

And this is what makes the relationship super fun in the beginning! Emotions and hormones peak. It’s relationship bliss!

See in green:

But over time, usually after the commitment phase, I’m no longer able or willing to put in the overtime effort.

My engagement and proactivity return back to baseline, and she is often disappointed.

This has come up as a complaint in some way shape or form in each relationship.

This is represented in the purple section below:

When she becomes unhappy/disappointed that things no longer feel the same as when we began, that’s when the complaints begin:

“I want to feel special again”
“I want to feel prioritized”
“I want to feel connected like we did in the beginning”
“I miss when you used to write me poems”
“I miss when we stayed up late, talking”

… and as a “good” SO, when I heard these complaints, I’d do my best to work on doing those things again.

Soo… basically, I’d just agree put in overtime hours every day.. in the name of being a “good” partner.

No bueno.

And that leads me to the next point.

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2. I’ve failed to be honest, forthright, and communicate

This is a generalization, but like most dudes, if you give me a problem, I’ll just try to fix it.

You want us to talk more frequently? Cool, let’s talk more.
You want to us to go on more dates? Cool, I’ll plan one.

But what’s the issue?

The reality is (and was), that in most of those moments I wasn’t *excited* about doing it.

But I agreed to do it because I felt like the cost to do it was worth the prevention of a future fights/conflicts/complaints.

One ounce of prevention is worth more than one pound of cure, right?

But what’s the long term consequence here?

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There’s a concept called “Distance Traveled” (DT) that my relating-guru-friend Norman shared with me once.

Not all asks are equal.

For one person, it might be incredibly easy.
For another person, it might be very effortful.

And even if it is the exact same ask, it’s not always equal depending on when it is requested.

For example, being asked to do dishes when:

• You have an open weekend and no plans VS

• You just came home from a long workday and have a lot of other things on your mind

… are not experienced the same way.

There is more “Distance Traveled” (DT) being asked to do the dishes when you’re tired and stressed than when you’re rested and spacious.

The higher the DT the more it costs.
The lower the DT, the less it costs.

The issue here is that DT is invisible to everyone except for the person experiencing it.

So let’s use a real example from my past:

So let’s say I have 10 “energy” points to spend every evening.

Let’s say my SO asks if I can provide some emotional support.

Let’s say that providing emotional support costs me 8 energy points.

Let’s say that I agree to provide emotional support.

That means that I’ve given 8 energy points to my SO and I only have 2 energy points left for myself.

Problems will arise when my SO thinks that providing emotional support only costs me 2 energy points.

And my biggest mistake was NOT proactively communicating around how much it actually cost me until I was already burnt out.

I have no problem providing emotional support every now and then.

Just like I generally don’t have a problem staying up late for work every now and then.

But if it happens too frequently (and it did), it would start feeling like I’m sacrificing too much of my time and energy.

Food for thought:

Very few would disagree that… if my job started demanding that I put in overtime hours consistently (without prior expectation setting or some upside compensation for it), that I should probably start looking for a different job… yet some (including my younger self) might argue that putting overtime effort in a relationship is expected. Interesting…

BUT, because this cost was invisible, my SO could not properly appreciate it, and often would ask for more.

And because I wanted to prevent future conflict/complaints, I’d keep saying yes.

In saying yes, I’d sacrifice more.

Rinse. Wash. Repeat until I’m deeply unhappy, my SO still wants more, and I have nothing left to give.

Yikes.

I’m now very conscious of my DT and have every intention to communicate this regularly and proactively in my next relationship.

3. I’ve done a poor job of evaluating for compatibility

This is exacerbated by the first point (expectations at the beginning of the relationship). 

During the initial, fun, chemistry pre-commitment phase, my experience suggests that both sides are incentivized to overlook and downplay potential yellow/red flags.

If I’m infatuated and enamored, I’m less prone to believe flags to be of genuine concern. 

And similarly, I’m also going to be less prone to be brutally honest about MY possible flags.

Examples of stuff I overlooked with past relationships:

• “Oh… she doesn’t seem to have a lot of friends, but she just moved to a new city, so of course she’s not going to have that many friends. I’m sure that’s not a big issue…”

• “She just told me that she’d rather just break up instead of taking space to work on her self-love/worth journey… ha, let’s stay together!”

• “Oh she’s super harsh/judgmental to particular groups of people, of course she won’t do that to me! And especially not during conflicts! Ha!”

Yes. I know... I too have hindsight now. 

The bottom line is that during the chemistry/fun getting-to-know-you-more-part of the relationship, it’s really hard to get reliable signals of compatibility on either side. 

Subtle things like:

• How does this person handle conflict when they’re stressed? 

• How compatible are our love languages? 

• What are their expectations around frequency and mode of communication? 

• What are their expectations of the role a SO plays in their life?

… aren’t the easiest to suss out until you get there.

So now what? 

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Here’s what I’m doing differently moving forward:

1. Just focusing on friendships first

2. Using a Date Me Doc (for online dating)

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1. Just focusing on friendships first

Why?

I’ll give you 6 reasons.

A) Longevity, Effort, Success %

With A LOT of effort, NONE of my 3 relationships have lasted more than 2 years. 

On the flipside, with what feels like ZERO effort, I’ve been able to maintain really fulfilling/meaningful friendships that last 5+ years. 

Lot of effort = 👎 outcome
No effort = 👍 outcome

I must be just a little bit crazy if I continue to do more of the former at the expense of the latter. 

What’s also frustrating is that despite the amount of effort that went into the long term relationships, the depth of connection that we built, and how well my SOs knew me, right now, the connection we have post-breakup is barely a fraction of what it was. All of the time and energy invested is kind of… just lost. 

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Right now with LTRs, I am 0 for 3.
I’m literally batting 0%.

I don’t have exact numbers with friendships, but I can tell you this:
It’s higher than 0%. 

It’s just silly when I look at it this way.  

B) Believable signals when it comes to compatibility 

With friends, there isn’t really any incentive to hide parts of yourself. 

When a friend of mine talks about how they’re super excited to travel around, live in community, and spend tons of time with people, great! I can trust that’s their baseline and mentally note that we’re probably not compatible in that area of life. 

If a friend consistently talks about going out to party and drink, same thing, I can celebrate whatever they’re interested in and the friendship isn’t jeopardized because of it.

Friendships don’t go to 0 because of hard incompatibilities. But often, romances do.

It could be their money habits, their fitness habits, or cleanliness. It’s easier to believe that those habits are true-er indicators of their baseline than if we were romantic and trying to get an accurate sense of those kinds of things. 

C) A better, stronger foundation for long term partnership

I don’t think it’s a stretch to assume that it’s *normal* for the sparks to fade after the initial honeymoon.

If we assume this is always going to happen, then we have to ask, “What is the foundation for the relationship after the sparks fade?”

Friendship makes sense as an answer.

But I think it’s pretty hard to cultivate a friendship *after* the sparks fade.

I don’t have personal experience with this yet, but I suspect that it’s easier to introduce romance and sparks to an existing friendship than it is to do it the other way around.

It’s also not to say that I’m proactively rooting for any of my friendships to become romantic — that’d be a little weird. It’s more to say that friendships feel way more worthwhile, meaningful, and sustainable for me in the long run, and if it happens that someone turns out to be super super compatible, I’d be willing to consider romance as a possibility.

D) Personal clarity and mental focus 

No more dating apps. 
No more wandering thoughts when I’m out and about, going to events and such. 
No more wondering if so-and-so is interested in me.

I no longer feel confident about successfully building a healthy, sustainable, life partnership through the traditional arc of modern romance (Chemistry —> Commitment —> Compatibility).

Of course I think it’s possible — plenty of people do it. 

But I don’t think it’s for me.

Opting out feels like I’m unloading a big chunk of mental bandwidth.

I feel lighter. 

I feel more focused and immersed in my relationship with myself, the things I’m creating, and supporting awesome friends. 

E) A healthy give and take 

There’s definitely bias in this statement. 

But overall, in all my long term relationships, I felt like I gave MUCH more than I got. 

It’s highly plausible that my SO’s also feel the same way for entirely different reasons, I don’t know for sure. 

This feels much less true when it comes to my friends. 

I feel like the give and take when it comes to my friendships have felt much more balanced.

It’s like the relationship bank account when I’m with a SO feels chronically negative, but with friends it feels chronically positive.

F) Sustainable expectations

Remember the super complicated expectations graph from the beginning?

Here it is again:

What a messy roller coaster.

Here’s what my proactivity and engagement in friendship looks like:

Here’s what I perceive as the expectation it creates for friends (in red):

Yeah.

No drama llamas.

It’s a no brainer for me!

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2. Using a Date Me Doc (for online dating)

So as I’ve mentioned, one of my biggest issues with modern dating is the fuzziness of compatibility when my (and likely her) judgement is clouded by infatuation.

In my mind, the Date Me doc solves a good chunk of that.

It’s so much easier to see lack of compatibility for what it is when there is nothing invested into the relationship, no infatuation, and no connection.

What is a date me doc? 

It’s basically what I think dating profiles *should* be if people were deeply reflective, fully honest, and upfront about how they do relationships, what they’re looking for, and what are the honest trade-offs are in being in a relationship with them. 

• The NYT wrote an article about Date Me docs in August 2023.

• This is a public Date Me doc directory (where mine is also submitted).

My Date Me doc is 15 pages and something I’ve put 10+ hours into crafting. The way I’ve tried to set it up is so that someone should have a pretty high-fidelity understanding of what it’d be like to be in a relationship with me… without being in one with me.

Results

When I first started drafting the document, I was just trying to condense all my learnings/reflections after getting out of my last relationship and getting clear for myself who/what I was looking for next. 

But since drafting it, I’ve had 3 people express interest — which is far more than I expected.

All in all, I don’t fully expect to meet my “person” through the Date Me doc, but it’s a pretty great way to have confidence that if someone reaches out to me because of it, I can trust that they:

1. Read most of the document

2. Feel a decent amount of compatibility/resonance despite all the trade-offs I listed

… and to me, that’s a fantastic way of saving a LOT of mutual heartache with relatively little effort invested on both sides.

No one wants to invest multiple months of time, money, emotion, and attention into a relationship only to discover significant incompatibilities down the road.

I’d rather be brutally honest up front and if things are still aligned, build something from there.

The Date Me doc achieves a lot towards that at scale without any heartache, disappointment, or attachment.

Closing Thoughts

What’s SUPER interesting is that I’ve kind of come full circle.

I grew up in a Christian environment that valued no-sex-before-marriage. We had men’s groups that consistently focused on our consistently-failing relationship with pornography/masturbation.

It was primarily a moral argument to approach relationships, partnership, and marriage in this way.

Needless to say, I didn’t really abide by this once I started questioning a lot of the moral/religious conditioning I grew up with in my early 20s.

But now… I find myself seeing the wisdom underneath it, as illustrated by this post.

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If you read all of this, you deserve a cookie! Thanks for taking the time.

Oh. And if you’re single and want to join an experiment (side project) I’ve been running, check it out here.

• It’s basically a way to find out in 7 days whether you might be dating in the wrong city — using data, of course :)

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When’s the next post coming out? I no longer have a regular cadence of publishing, but new posts will always come out on Sundays at 12pm Pacific (3pm Eastern, 3am Singapore, 8pm UK).