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.

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?”

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

It’s nice to smile and have someone smile back. For no reason other than we’re two strangers doing the same thing and acknowledging each other’s existence for a second.

Dating involves a series of decisions. Some are minor and straightforward, others are complicated and emotion-laden.

Flirting isn’t a test you pass or fail. It’s a social skill. And like any skill, we all start out as bumbling beginners.

Perhaps you, too, feel like flirting is something other people do, especially if it’s been a while since you last dated anyone.

Part of the problem was my definition.

Ever wonder why some dates seem to go nowhere, despite your best efforts? Or why someone you thought was “just okay” at first becomes attractive after a few interactions?

So, you went on a date, thought it went well, and then... nothing. No second date. Maybe they politely declined. Maybe they ghosted. Or maybe you got unmatched after expressing interest.

We hear a lot about emotional intelligence these days — but before you get to maturity or communication, it all starts with something simpler (and often overlooked): awareness.

This first date guide is for anyone who’s never had one, hasn’t had a good one, or hasn’t had one in a while.

Alright, let’s get this out of the way: first dates are awkward.