Dating in the modern era doesn't feel romantic, it feels operational.

Lots of first dates. Some good conversations. Plenty of "we should see each other again." and almost nothing ever converts

Somewhere along the way, dating stopped feeling like a rom-com and started behaving like a broken sales funnel: massive volume at the top, endless qualification in the middle, constant objections, and almost no real closes.

After enough good dates that went nowhere, I stopped asking what I was doing wrong and started asking a different question:

What if the problem isn't me, what if the system is bad at closing?

You're not bad at dating.

The system is bad at closing.

How you get your Leads?:

There are two types of leads, cold and warm.

Cold leads:

Dating apps Cold approaches Online Interactions These generate high volume, but very little context.

You don't know their intent, emotional availability, or actual readiness

Cold leads feel efficient, but they’re expensive in a different way: they cost time, attention, and emotional energy.

Warm leads:

Friends of friends Being a regular somewhere Shared communities: Sports leagues, church outings, book clubs

Warm leads move slower but the arrive with social proof, context, and accountability.

You are not starting at zero.

We have traded depth for reach, and then wonder why nothing sticks.

Almost every strong relationship I know came from a warm introduction, not a swipe.

Mapping the funnel:

Stage 1: Qualify (The Swipe/First Impression)

At this point everything is new. Everyone is rushing around trying to figure out if this product is a fit. Or if this even brings value to your company. Does it fit our budget? Who do we need to sign off? When is this moving to the next step?

Similar to dating with the introduction of swipe culture. You get your surface level qualifications: Height, job, vibe, hair color... Everyone is filtering, no one is diving that deep.

In this stage you can get disqualified before you ever speak. Or worse you qualify each other on fantasy instead of reality.

Stage 2: Develop the Lead (The First Few Dates)

In this stage of the funnel you are building trust with clients and learning about their problems. The ultimate goal to show them the value.

You might be showing them how buying a data center will decrease their costs. Or this new server has lower network overhead. Proving to the prospect that this is good for them. This stage is about proof.

In the dating realm. Building trust equates to texting cadence. We all know the rule, or it seems to be unwritten. That you shouldn't respond back so fast it might make you look desperate. If you text back super fast they might stop talking to you.

How else are you supposed to learn about the person without talking to them?

I went on a date a while back (this was many months ago). We had dinner, nothing fancy. Got a bite to eat, it really only lasted an hour. Which I wanted. I wanted to keep it snappy, to preserve the "mystery." We asked each other the first ate questions. You know the ones. "Where are you from?" "How long have you lived here?" "Where is the coolest place you have travelled to?" "Do you like sports?". The surface level things. Just trying to gauge if I wanted a second date.

Spoiler, I did.

She seemed like she did as well. She was engaged the whole time. Caring about my answers.

As we were leaving I said to her, "I had a great time, we should go play basketball next time. (PS: she likes basketball, and plays it)" "Yea, I like that idea. Let's do it again."

I texted her the next morning saying "I just devoured my leftovers. Thanks for rescheduling, I had a really great time."

Silence. No text till this day. I got Bamboozled.

People say they had a great time. You believe them. Then the lead goes silent overnight.

It just made me realize that sometimes people optimize for pleasant interactions. Not so much honest ones. No one wants to deliver that fatal blow, "No." I get it, I am the same way.

I will give her the benefit of the doubt, maybe she was nervous or realized she didn't like me. Or it is possible that the text I sent was as dry as the chicken we ate. All totally ok, there is not one way to handle it these kinds of things. We are all just figuring it out.

Stage 3: Pipeline (Situationship Hell)

This is the longest of the 5 stages. If you are reading this you have probably had something like a situationship. Going back and forth trying to figure out what this is. Are we dating? What are we? Do we like each other? Similar in sales, these are where opportunities look promising, but eventually stall.

In sales the pipeline feels productive. It looks busy and it reassures leadership. It is an essential step. In this stage it is sort of up in the air. Everyone is talking to a few people, they are keeping their leads warm, and most are avoiding exclusivity. Modern dating is more mutli-threaded that monogamous. At least in the early stages.

It seems like no one is urgent. Sales relies on urgency.

There in lies the problem I call "Let's See Where This Goes."

It sounds open-minded, mature, and safe. All essential things in dating someone. Functionally it means no timeline, unfettered expectations, and zero accountability. It is not "enforceable", like the contracts we sign.

"Let's see where this goes" is just pipeline purgatory with better branding.

Sometimes you crack through, and find someone who is interested in hanging out with. You get along well together, you communicate with each other constantly. Always being in contact, never falling out of touch. You think to yourself "This might the one". Then gone without a trace. One day they just stop responding.

You have just been ghosted. Most people think ghosting is cruel and unfair. It is more often avoidance than anything else. Sometimes deals don't get killed, they just stop getting replies.

Presently, there is just so much stimulus for prospects. When dating you lug around you old baggage, time commitments to your friends or getting constant stimulus just by swiping. Dating apps add another layer of complexity, as it is all gamified. The apps are designed to keep you on the app. That is a topic for another time.

None of these measure intent or readiness to choose. We optimize for engagement instead of outcomes.

This makes a deal stall because no one wants to push. No one wants to ask the tough questions of "Where is this headed?" or "What are we doing?"

So everyone waits. And waiting slowly kills the deal.

I fall victim to this myself. Not labelling anything, because I was too scared to move to the next stage. Or limiting my upside with constraining my emotional budget.

The pipeline isn’t where you find love. It’s where you learn how long you’re willing to wait without clarity.

Stage 4: Upside/Validate Requirements (The Scary Conversations)

This is the stage where real things either prosper or shatter. This is where you confirm your real needs, align expectations, and hopefully remove risk.

Similar to sales, in dating these are the make or break conversations.

The questions you must ask, in order to know if this is someone you can spend your life with.

"What are you actually looking for?"

"Do you want kids? Stability? Growth?"

This is where all the risk takes place. It is the scariest part of it all. These moments are where you might scare the prospect off. People avoid requirements validation because it might disqualify the deal.

So they postpone truth until the truth kills it anyway.

Stage 5: Commit (Marriage, or Something Real)

This is the part of the deal where all parties involved are happy with what they have seen. They are ready to sign the contract. At this stage there is mutual buy in.

In dating this means exclusivity and shared direction.

This all means choosing someone even when "better leads" might exist.

In an infinte-choice market, commitment feels like a bad decision. However, that is the only way value compounds. By sticking with something for the long term.

Objection handling (The Real Close):

Dating advice loves the idea of objection handling because it offers "control".

If someone says "I'm not ready," reassure them. If they pull away, give them space. If they ghost, assume you mishandled the follow-up.

This framing is comforting because it suggests every outcome is fixable, as long as you say the right thing.

But objection handling only works when the deal is fundamentally viable.

In dating, many objections aren't objections at all. They are polite no's. Soft exits. Signals that the other person doesn't want to choose. Not you specifically, but anyone. They could not like you, that is never off the table.

However, no amount of reassurance can manufacture readiness.

No amount of patience can create urgency.

Not every objection is meant to be handled. Some are meant to be heard.

The mistake is not failing to overcome resistance, it is staying in the pipeline when the signal is clear.

In both sales and dating, qualification beats persuasion every time.

The real goal isn't to close every deal. It's to find one that doesn't require convincing.