Before deciding what to do next in dating, it helps to understand where you actually are.

Once people understand the fear behind disclosure and have a better sense of timing, the next question is tactical:

“So… how do I actually say it?”

This is where many people get stuck.

Once people understand the fear behind disclosure, the next natural question is: “So… when do I actually bring it up?”

Most daters ask this about things with emotional or practical significance.

Many daters hesitate before sharing something personal — divorce, kids, chronic illness, or anything with a complicated impact. We want to communicate openly and also protect the connection. This tension makes disclosure feel more daunting than it needs to be.

In almost every conversation about meeting people offline, someone eventually asks:

“But… how do I know if they’re single?”

A lot of people think “good texting” means being witty, fast, charming, cool-but-not-too-cool. But the texting that tends to actually work keeps the momentum going and leads to real connection.

If you’ve spent any time on dating apps, you’ve probably felt the same frustration from multiple directions.

I piloted a new event this week called Let’s Talk — a one-hour online session where people pair up for short conversations using thoughtful prompts.

At the end of event, I asked everyone a simple question:

“What makes for a better conversation?”

We spend a lot of time trying to read between the lines.

Did they really mean it?

Were they just being polite?

What was that tone?

Part 4 was about practicing deeper conversations, this one’s about keeping the momentum going.

So you’ve made it past the small talk. Now what?

“Hi, how’s your day?”
“How’s your weekend going?”
“What are your plans for this weekend?”

They’re all polite, familiar, and easy to ask, but they usually end the same way.