What To Talk About on a Second Date!

Project 50 First Dates—First 2nd Date!

Just before we get to what to talk about on a second date…

If you’re just tuning in, I did a 50 first dates project several years ago when I’d just started coaching.

We’re reviewing some of those real fake dates so you can learn from them!

Interestingly enough, First Date #1 (The G Man) who blew it after the first 1st date—details to follow—and then made a big recovery—hold your horses, I’ll get to it—ended up coming in as my first 2nd date.

You still with me?


So what do you talk about on a second date?

A quick recap…

The G Man was handsome but bashful with praise. He worked for the government and had no kids (at the time of our date).

I’d enjoyed his company but didn’t feel sexually attracted to him.


Not feeling an instant attraction is way more common for women to experience than men!

He’d originally blew it because I had to repeatedly remind him that I. detest. texting.

I know, it’s weird but it’s true. From my research most women looove to text-chat. (Not I.)

BTW, if there are any ladies reading this, a guy who’s interested will be text-chat attentive.

As far as I’m concerned, text is for information—time, location, direction—not conversation.

More on that in another blog post―for now back to The G Man.

He finally got that I no likey texty and respected my “no text-chat” request.

Wingmam motto reminder: Always leave them wanting more.

He’d asked me out again but by then I was busy with sad “family stuff.”

A while later, I had a slot to fill, *wink* and because he’d respected my no-text requests, I asked him on a “sort of” second date.

“Sort of” because I’d invited him to an event with the intention of setting him up with someone else. *Shrug* at least I had love intentions.

I met him at the event—significant—which was a book launch and signing for a girl friend’s first book—we’ll call her Sparkle.

The venue was abuzz with social energy and was insanely noisy.

I gave her a hug and whispered, “I brought you a present” and nod toward The G Man.

I introduced them and she subtlety gave him the once over with an approving twinkle in her eye while he glanced around the shop.

But she had books to sign and adorning fans to thank—significant—and I could tell he was overwhelmed by the bustle, so The G Man and I took an early leave to go next door for a coffee.

Significant bits:

  • I met The G Man at the event instead of having him pick me up to re-establish our friends-only relationship. Going “with” him sends a different message. I would’ve had to explicitly reject him as a romantic partner if I went with him. Men don’t speak hint.
  • As a loyal and trusty Wingmam, bringing The G Man to my friend’s event was a 5-star friend move—it allowed him to see her best self: looking sexy, being adored, juiced-up (energized), accomplished and happy.

At the coffee shop …

He knew I’d been out of town—sad, sad stuff; I’m okay now, thanks, though.

So what to talk about on a second date / not-date?


He’d lost a loved one a couple years beforehand so the topic didn’t wig him out.

Do I recommend talking about death on a second date?

Sure. Go ahead, if—

  • you can hold yourself together without becoming a messy puddle
  • you’re not feeling needy, clingy or extra desperate because of it
  • the other person is comfortable with the topic

I expect most of you have either experienced someone having passed away or have developed some level of compassion from experiencing other past pains.

Serious topics—death, politics, religion, children/parenting, aging parents, money, and monogamy —can be good topics for what to talk about on a second date as long as you can weave some fun and playfulness into the conversation somewhere.

You’ll likely need to veer into another lighter topic to do this, but do. Too heavy is just too heavy!

At the same time, you want to settle down without settling, right?

Part of discovering whether or not you could nest with the person sitting in front of you is finding out where they stand on your seriously-need-to-be-considered topics.

You already know you like each other or you wouldn’t even be wondering what to talk about on a second date with her.

What to Talk About on a Second Date Takeaways:

  1. Even if you love texting, leave something to talk about in person.
  2. Uncomfortable conversations about loved ones “leaving this world” can fast-track intimacy—in-to-me-see. You’ll find out a lot more about the other person and whether you want to risk Date #3. Or leave it on the table. Hint: Don’t try to cover all the heavy topics on Date #2!
  3. Don’t do Date #2 at either of your residences. Lead thee not into temptation! Or awkwardness. Try to hold out until you know if you want to bump nasties long term, or you risk ignoring red flags.
  4. Second dates are a good time to start the weeding-out process by talking about touchy subjects that aren’t for touchy-feely-2nd-base activities. If you want to get into her for the long run, get to know her in the short run. (Your batting average will go up if you can keep “it” down for now.)
  5. Never date anyone when you’re on the verge of a breakdown—it sets an unhealthy relationship dynamic. If you win the other person over, you’ll need to remain broken forever to keep them (and you) interested in the relationship.

Holy crap, this was a long, serious one.

Are you still here?

If yes, thank you. Really.

My first 2nd date summary …

Unfortunately, the conversation about death created too much intimacy for The G Man for me to wingmam him over to a much better match: my friend, Sparkle. Bad wingmam.

Note: I have these types of conversations with everyone/anyone; this particular conversation had no extra effect on me.

I’m no more attracted to The G Man than I was on our first real fake date.

Just because you’re attracted to her and feel a connection does not mean she feels the same way!


If find yourself always in the friend zone instead of the end zone, get my WakeUP2Luv program and check out this playlist:

About the Author Anna Jorgensen

Vancouver dating coach for men who love women! ❤️ (Not PC and not a feminist.)

Leave a Comment:

Monty Steele says October 27, 2017

I’d love to hear about “How To Avoid The Friend Zone” as a topic or perhaps, “What to do if you land in the Friend Zone?”

Randy Hathaway says August 27, 2020

In your excellent e-blurb re. 2nd dates, I bumped into the 2nd-most common e-felony, as follows (you will read it twice before saying, “Aha,” or worse.):

“(You’re batting average will go up if you can keep “it” down for now.)”

Blush not. Its an easy mistake to make.

    Anna Jorgensen says August 28, 2020

    I did have to read it twice! lol …Thank you! #corrected That’s a mistake I loathe!! 😉

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