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5 First Date Conversation Tips for Guys That Work

5 First Date Conversation Tips for Guys That Work

5 First Date Conversation Tips for Guys That Work

Looking for a few first date conversation tips? If so, you’re in the right place.

In 2012-2013 I went on 101 dates with 52 different men.

At moments it was beautiful being able to quickly form a bond with a complete stranger, while at other times I was bored out of my mind listening to dudes rattle on about their money, status, and ability to do a 5-minute keg-stand (this was in college after all).

My 100 date experiment was many things, one of them, was enlightening.

The hundreds of hours I invested in meeting new men and going on first dates taught me exactly what does and doesn’t work when it comes to having a quality first date conversation.

A first date is the most fragile period of any nascent relationship. Considering that you’re dating a more or less stranger, you don’t have much room for error. She doesn’t know you and you don’t know her. Any slip up may result in never seeing her again. Luckily, you don’t have to do too much on a first date.

Here are five first date conversation tips that when employed will guarantee a second date.

5 First Date Conversation Tips for Guys, That Work!

Let’s first understand the purpose of a first date.

It isn’t to convince a woman to sleep with you or make her fall in love with you.

A first date is nothing more than an introduction. It’s where two parties meet to figure out if there’s any connection. It’s this first date where both you and the woman sitting across from you attempt to enjoy each other and investigate romantic potential. These are the two primary goals of a first date.

The purpose of these goals led me to create a MegaDating strategy that recommends that a first date last no longer than one hour, with no more than $10 being spent on the date.

It’s with these goals and format in mind that we introduce these first date conversation tips.

1. Talk 20% Of The Time

Men have a tendency of acting selfish on a first date.

In no way does this selfishness manifest itself more than when it comes to dominating the conversation.

There are a few reasons men hog the mic on a first date.

For one, they’re scared. When we’re scared or anxious we tend to act differently. Perhaps you normally would ramble on about yourself, but nerves tend to get the best of people on a first date.

Another reason dudes turn loquacious on a first date is because they feel the need to convince a woman of their worth. Naturally, men see the best way to do this is to talk about their hobbies, jobs, friends, cashflow, and how awesome their life is in general.

A third reason dudes romantically filibuster on a first date is because they don’t give a damn about their date. Perhaps you were never that jazzed to see her or once you saw her she didn’t look anything like her photos. So instead of trying to get the most out of the date -or choose to act like a gentleman- dudes just decide to stroke their own ego and make the night about themselves.

Don’t be a dick.

Just because you’re not feeling the date doesn’t mean you need to ruin the date for the both of you.

Again, this is why I recommend MegaDating. Worst case you aren’t into the woman, no worries, you’ll be out of there in less than an hour if you adhere to MD rules.

Instead of talking about yourself for the entirety of the one-hour date, keep your words tucked under your tongue. Try talking for around 20% of the date, leaving her the other 80%.

Whenever you get someone talking about themself, they come to the conclusion that you’re an awesome conversationalist. This is more likely than not because people love talking about themselves and being listened to. If someone peppers me with questions on a date it indicates interest.

Look, every woman wants to be valued.

Keeping her talking is the best way to create mystery, make her feel appreciated, and learn more about the woman you’re debating seeing again.


For the next five interactions, try to talk for no more than 20% of the conversation. Practice on friends, family members, and acquaintances so that when you go on the first date, you already have the strategy mastered.

In Andrew Carnegie’s best-selling book, How to Win Friends And Influence People, he found that when he just listened intently people enjoyed being in his presence more, “I was this and I was that, and she ended by saying I was a “most interesting conversationalist.” An interesting conversationalist? Why I had said hardly anything at all. All she wanted was an interested listener, so she could expand her ego and tell about where she had been.“

2. Ask The Right Questions

First date conversation tips

The right question is the one that you’re interested in learning the answer to.

It’s difficult to listen 40 minutes out of 60. I get that.

What makes the process a hell of a lot more meaningful is by asking questions that you care about. Don’t ask her about her job or how long it took her to get to the date location. She doesn’t want to talk about how she looks or her favorite food either.

Ask her probing, stimulating questions that will make her think and make you listen.

To ensure that you’re asking the right questions keep these tips in mind.

Ask questions that pique her interest. Once she’s into the topic, ask her even deeper questions about the same subject.

If she’s doesn’t feel 100% comfortable opening up about topics, make her feel comfortable. Do this by smiling, remaining relaxed, and staying engaged. When needed, share your thoughts, just make sure you’re not being combative or voicing any super strong and possibly conflicting opinions, like politics.

While it’s important that you listen, it’s also important to remember.

Bringing up topics or opinions of hers on the second date that she spoke about on the first will win you serious brownie points.

And remember, the date isn’t only about her. Your feelings matter too. That’s why you should only ask questions you care about. If she starts talking about Jeffree Star, steer the conversation back towards something you care to process.

3. Stay Positive

First date conversation tips

No one wants to talk about how crappy their job is or the vitamin D deficiency they developed during quarantine on a first date.

You want to be associated with positivity. You want her leaving the date thinking about how awesome that conversation was. She won’t want to see you again if you were complaining about the food, the weather, and how garbage the season finale of Game Of Thrones was.

Being that your date will last no more than an hour, each comment of yours becomes magnified. She knows nothing about you. The likelihood that you’ll score a second date will be wholly based on how dope the first one was. This means keeping things light and positive.

Avoid taboo subjects, work, and vanity topics.

Speaking of which…

4. Stop Talking About Status Symbols

I can’t tell you how many guys told me how much money they have in their bank account on the first date.

Frankly, it’s insulting when dudes throw status symbols in my face.

When a dude says he drives a Tesla or has wads of cash lying around, it feels like he’s doing so because he thinks by flaunting his social status he’ll be able to take a woman home.

As if all she cared about was how much money he had.

As if valued was defined by how much money he has in his bank account.

Sure, there are some women that will be blown away by how much bread you bake, but if this is the foundation of her attraction, it won’t last long.

Maybe your flash will win you a second date or even a third, but if you don’t have some substance to back up all that flash, this relationship isn’t going anywhere.

5. Read The News

First date conversation tips

An odd first date conversation tips I’ll concede that, but think about it.

Every dater’s biggest first date fear is that you’ll have nothing to talk about. That you two will be polar opposites, that the convo will run flat, that awkward silence will blow a hole in your chances of a second date.

Combat these worries by reading the news.

It’s timely subjects like the ones we find on the news that you two can easily comment on. It doesn’t matter how different your interests are, nowadays there’s always some juice current event going on that’s worth discussing.

It’ll also look bad if she says, “hey did you see what happened in Philly today” and you have no idea what she’s talking about. Being socially aware will make you a much more dynamic dater.

At a bare minimum, download the google app on your smartphone and save a couple of “world related” topics. They’ll feed you news worthy articles without much daily effort on your part.

Are You Ready For A First Date?

First date conversation tips

Now that we’ve covered first date conversation tips, are you ready to get out there?

If not, is it because you’re struggling to find women to date?

When you learn the emlovz MegaDating blueprint you’ll not only learn how to become an expert dater, but also how to find women to date. I’ll teach you how to meet women IRL and through dating apps so that you’ll be dating multiple women a week.

If you’re too busy to find women, no worries, focus on your work while my matchmaking team and I do the rest. My team of skilled recruiters will scour your city looking for women that you’re compatible with.

Book a 1-on-1 Zoom session today and find out how our coaching and matchmaking services can help you reach your dating goals in just 3 months.

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