First Date Conversation: Expert Reveals the Do’s & Don’ts

first date conversation

When it Comes to First Date Conversation, There’s a Lot to Consider — Do You Know These Expert Tricks?

First dates seem to always be a little nerve-wracking.

You’ve gotta figure out what to wear…

Where to go…

And, of course, what to say.

A lot of guys come to me with questions about first date conversation, so today I want to show you exactly how to navigate it like a pro.

Here are my top 5 tips to nail your first date, no matter where it is or what you’re doing:

Do You Know These Expert Tricks?

Tip #1: Don’t Ask Non-Stop Questions

One of the most useful skills a guy can have in his sexual wheelhouse is the ability to glean information without asking questions.

First, this is great because I don’t recommend asking tons of questions in your first meeting or on a first date.

In fact, I’d actually recommend against a lot of questions in the “getting to know her” phase.


Questions tend to take too much control over the conversation — asking about something she thinks is boring, for example, can drive the conversation into a dead end.

On top of that, questions also require rapport or power.

She can simply refuse to answer you if you don’t have rapport — especially if it’s a question that makes her uncomfortable.

Ultimately, a first date is not a job interview. And as such, it shouldn’t feel like one.

Not asking too many questions will help her feel more comfortable with you, and less like she’s on a first date with a complete stranger.

Do You Know These Expert Tricks?

Tip #2: Don’t Directly Answer All of Her Questions

My next tip is also related to questions — but it’s about the ones she asks instead.

Take it from me: directly answering every question she asks you is not attractive (unless you can manage to do it in the way Tommy Lee Jones does).

So how exactly do you avoid answering her questions if she’s asking a lot?

First, let’s talk about why women do this. It’s because she’s “filtering” for whether or not she wants to have sex with you.

And that paradigm rarely ends in the deep down desire you want her to feel, which is why it’s a bad idea to immediately answer all of her questions.

My next tip will show you how to combat this problem.

Do You Know These Expert Tricks?

Tip #3: If You Do Have to Answer, Answer Vaguely

Sometimes, you do have to answer her questions directly.

Some women — especially if she thinks you like her — will pepper you with a barrage of questions, and maybe you’re too interested to resist.

If that’s the case, then make the most of it.

I’ll show you how with this example. Let’s say she asks you, “What do you do?”

Here’s an A+ response:

“I work downtown at City Hall. You know that crane that took out two floors of a building? That’s right across the street from my office. That was a wild week. Do you eat meat?”

Now, let’s break it down to understand why this response is so effective.

First, when you say “I work downtown,” you’re leaving out some key information (what you do as a job). That way, she’ll still have a question to ask you if she gets nervous and doesn’t know what else to say.

And when you say, “You know that crane…,” you’ve effectively turned the question on its head. You’re adding in new information that could potentially spark a completely new conversation.

Which brings me to my next tip…

Do You Know These Expert Tricks?

Tip #4: Drop Conversation “Bread Crumbs” to Keep Things Flowing

With that answer, you’ve given her a very visual, very interesting subject for discussion. This is what I like to call dropping conversation “bread crumbs.”

Most likely, she’s only asking the boring questions (“What do you do?”) to make conversation.

And by giving her this kind of answer, you’ve given her something else more distracting, interesting, and salient to ask about.

She could ask any number of things:

“Did you see it?”…

“Were you at work when it happened?”…

“Do you know anyone who got injured?”…

And so on.

Note that she may not take this bait at all. However, the extra story keeps her from realizing that the original question has not yet been sufficiently answered.

(Trust me — telling her, “I’m a human rights lawyer” won’t do much for your conversation.)

Do You Know These Expert Tricks?

Tip #5: Change the Subject Early & Often

Back to the A+ answer you gave earlier — you may have noticed that it ends in a non-sequitur (“Do you eat meat?”).

This is a great example of one of the best pieces of dating advice I can give you:

Change the subject during your conversations.

What risks making a conversation boring is staying on, or using up, a topic. By changing the subject often, you increase your chances of addressing a few super engaging topics.

Of course, you’re not trying to appear “ADD.” Normal conversation — especially engaging conversation between two people who are having a great time — tends to shift topic often and leave many conversational threads hanging.

Remember, you do not have to finish everything you start to say. And on the contrary, you actually get more by letting her ask for the continuation of the stories she’s really interested in.

So when you do decide to change the subject, make it different, yes, but also make sure it’s at least a little connected to what you’re doing.

When I wrote, “Do you eat meat?” for example, I’m imagining you are in a restaurant.

As you are looking at the menu, a question like “Do you eat meat?” makes sense and immediately changes the subject…

Closes the previous answer…

And adds a fourth topic for discussion. (Jobs, City Hall, the crane accident and vegetarianism are all on the table at this point.)


But if you’d really like to “seal the deal” at the end of your date… then it’s best to prepare yourself before the date ever begins.

Here’s how to do that:

Do You Know These Expert Tricks?

BONUS: How to Set Yourself Up for Sexual Success Before the Date Begins…

A lot of my buddies will ask me before a date:

“David, I’m so nervous… what if I run out of things to say?”

“Should I kiss her when it’s over? And how do I know if she wants me to?”

“What if she offers to split the bill? Should I let her?”

And ya know… sometimes, I have answers (Like yes, you should definitely kiss her at the end of the date. Check this out to see why.). But unless I can be with you on that date… I’m not gonna have answers for everything.

All this uncertainty can feel downright soul-crushing at times… especially with so many unanswered questions. Which got me thinking:

What if there was a way to know exactly what a woman wanted, without ever asking her…?

What if you could reliably predict what she would say & do on a date, before the date ever begins…?

I used to think it was some kinda pipe dream… until a close confidant & fellow dating expert introduced me to this “Dating Playbook.”

Using thousands of studies… real online dating conversations… and advice from hundreds of sex & dating experts… they were able to develop this badass “playbook,” which shows you what single women today really want in a man…

…how to know what she’ll do on your date (& how you should respond)…

…And they even figured out exactly what most women need to hear, before they’ll say “yes” to a drink back at your place.

Why hadn’t I seen this “Dating Playbook” before? I honestly dunno… but that’s not the point.

The point is, if you’re a single guy who’s looking for a little help… or if you just want to be as prepared as possible before your date… then this should help you a lot:

Get the “Dating Playbook” for Ultimate Sexual Success on A Date…