Seven Tips To Make That First Date Conversation Easier

September 9, 2020

There are no two ways about it, first dates can be an intimidating, nerve-wracking experience. Done right though, they are also a whole lot of fun. Use that nervous energy and excitement to your advantage and enjoy getting to know the other person.

Something we all tend to forget on these first dates is that you are both feeling the same way. No matter how calm and confident the other person seems, they are a little nervous too and that is a good thing. If neither of you was nervous, it would be because you just do not want to be there!

The downside to this nervous energy? The pressure can see some of us struggle for a conversation on the first date. It is okay though, that is where I come in. I am about to give you seven very simple tips to make that first date conversation so much easier.

By the end, I want you to feel just as excited as I am for every first date experience! Let us take a look:

Be Authentic (It Is Okay If You Are Nervous)

Being open about your nerves can be a very powerful thing on your first date. Even as someone that has been on hundreds, I will even use this on occasion. 

Why? Because talking about your nerves takes away so much of their power. Since she is probably feeling nervous too, it is an easy point for us both to relate on right from the start.

On top of that, it shows that I care about the outcome of this date and actively want to be there. A simple “wow, I am actually kind of nervous haha” is literally all it takes. The key is to be authentic without degrading yourself. For example, you do not want to start the conversation with “I do not get many dates, so I am not very good at this.”

Confidence and authenticity. You just need to find your balance.

Confidence Is A Big Deal

Leading on from that point, confidence is so important to every part of your dating life. It is a trait we all find universally attractive, even outside of the dating world.

In fact, dieting and body image come in as the second biggest killer of relationships. Second only to past relationships. Clearly a major faux pas, but also very easily fixed.

Do not be afraid to make decisions, be assertive, and lead the conversation. Just a word of warning though, there is a fine line between confidence and arrogance. Make sure you do not cross it!

As an example, “After this drink, we should head to that new bar on 4th” is confidence. “Finish your drink, we are going somewhere better” is rude and a little arrogant.

Positive People Are Fun To Be Around

Another trait that all humans appreciate being around is positivity. Self-deprecating humor has its place sometimes, but for the most part, keep it positive. Even if things are not quite going to plan for the two of you, make sure you focus on the positive aspects.

For example, I recently went on a first date at a bar that required reservations. There was some kind of error with their booking system and so they did not have our reservation.

At this moment, I had two choices. I could voice my frustration, saying that I made the reservation and now it is ruined our night or I could (and did) stay positive. “That is okay, looks like we are going on an adventure!”, holding out my elbow to jokingly escort her down the street.

Positivity is far more pleasant to engage with, so it makes for easier conversation every time.

Look Good, Smell Good

This also ties into both positivity and confidence because when you look good, you feel good. You want to show up feeling well-rested, well dressed and immaculately groomed every time. No questions.

When Esquire asked almost 10,000 women about their preferences on men’s facial hair, the result was clear: Clean-shaven and stubble are hot, full beards are not. 47% preferred clean-shaven, 45% preferred stubble, and just 8% actually like a full beard.

What does this have to do with an easy first date conversation? The more attractive you are to the other person, the more interested they are in chatting with you. It really is that simple.

When you are sitting there well groomed, well dressed, confident, and showing a positive attitude, who would not want to talk to you?

Practice Conversation Threading

Conversation threading is a skill that will help you hold a conversation in literally any context. It is about picking an interesting part of what the other person has said and running with that on a tangent.

The reason it works for endless conversation is you can pull several conversation topics from most sentences. It can take a bit of practice to get better at, but we all do it to some extent.

Ask Questions You Actually Want The Answers To

While you are working on that skill, questions are a great backup plan to make sure you never run out of things to say. The types of questions you ask will depend on your personality and the context of the date. Just make sure they are not too deep or complex yet. For a first date, simple, spending some time checking out our favorite list of fun and flirty questions to ask a girl is a great thing to do. This is a great list of questions to fall back on when you run out of things to say and want to keep the conversation flowing.

So long as you are asking questions you are interested in, one question can easily give you 20 minutes of conversation. They will have no trouble answering a question about themselves. Since you are paying attention to the answer, you can ask additional follow-up questions.

You might start out asking about her motorcycle tour through India and enjoying the stories. Before you know it, you are both exchanging wild travel stories from other countries.

Humor Is Your Friend

My final tip to make that first date conversation simple is to bring humor into it. Everyone has their own brand of humor, so figure out what works for you and run with it.

For me, “funny” is the best compliment I can ever receive from a first date. That is because if she thinks I am funny, it means she had a good time. “He was so funny, I hated talking to him” is not a sentence you will ever hear.

Dry, difficult conversation comes from boring topics or someone focusing on themselves the whole time. When the two of you are laughing and enjoying each other’s company, getting to know them happens seamlessly.

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Andi Perullo de Ledesma

I am Andi Perullo de Ledesma, a Chinese Medicine Doctor and Travel Photojournalist in Charlotte, NC. I am also wife to Lucas and mother to Joaquín. Follow us as we explore life and the world one beautiful adventure at a time.

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