First Date Conversation – Hold Her Interest

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First Date Conversation – Tips, Starters, and More 

You’re face to face, or soon to be, your first date is planned, you don’t want to ruin it by saying the wrong thing. First dates are tough, they can be awkward, you’re under pressure to look good, talk well, you want to connect with her, impress her, you want her to want to come back.

This is key – you want her to want to come back.


Imagine you’re this guy, even if you’ve not been before

You’re sitting across the table from your date, she’s eagerly leaning in, resting her chin on her hand and smiling. You’re talking, she laughs and nods her head. All her attention is on you.  Somehow you know you’ve got this date wrapped around your finger. You’re interesting. You’re engaging. You know if you ask her out again, she will say yes.


Do not put your date on a pedestal

Everyone gets nervous on a first date – hot girls and hot guys. Nerves are normal. When I was an escort, it took me a solid year before I stopped getting butterflies. However, you chose to be on this date, so did they. It may feel like you’re the one being tested, but do not put your date on a pedestal. They’re human, just like you. They make mistakes, they question what they say, they worry about saying something that makes no sense.

If you really like this person uncertainty and insecurity can feel oppressive. There were a lot of steps just to get here, you don’t want to screw up, say the wrong thing, or lose your chance at having a second date.  First dates do get easier with practice, I assure you, and if you’re just beginning to practice, here are some things to keep in mind for your first date conversation.


√ This date isn’t just about them, it’s also about you

We hastily focus our thoughts, time and energy on attempting to impress and compete to be the ‘best date’ this person has been on. However, you barely even know this person … don’t overlook the fact this date is an opportunity to learn more about them.

Flip it around. Turn the tables. This date gives you time to evaluate if you even want to go on a second date with them.


√ Here’s what can happen with first date conversation

  • They ask you questions (and you answer)
  • You ask them questions (and they answer)
  • If you’re nervous, ask more than you answer (this is a good rule to follow anyway)

Conversation is a two-way street. You talk about yourself and ask them questions about themselves. This is the most important thing you can do on a first date.


√ Impressing her is not the goal

Do not look at the conversation as if YOU have to impress HER. The objective of conversation is to engage. To engage in conversation means to communicate with by means of spoken words. It’s not to list your talents, smooth talk, or finesse her. The objective of your conversation is to get her to want more. If you watched my video on making small talk, or read my article How to Master Small Talk- remember your goal. The goal with small talk is to get your foot in the door. So here you are, your foot is in the door and she’s interested.

The goal with first date conversation is to get her to want more & to learn more about her. 

Define your goals

  • To get her to want more – Do that by engaging.
  • To learn more about her – Do that by engaging.

Couple on a date at a cafe

Good rule of thumb to follow – tips for first date conversation 

  1. People like to talk about themselves – it makes them feel in control because they know the answers.
    Bring up what you do know about them – if you met on a dating site, pick up on something they mentioned, like a hobby, a trip they took, something you noticed in one of their pictures, where they went to school, and look it up online. Do your research. Know something about it so you can hold a conversation. And think of a few questions surrounding that topic. Jot those down in your phone
  2. Ask their opinion – it makes them feel valued.
    I was thinking of going _______ for a trip, do you know anything about that place? I was thinking about doing this ________. Asking opinions shows them you are listening and that you care about their opinion.
  3. Look for things you share in common – sameness.
    Humans naturally try to align themselves with others, we all do. When we meet someone we immediately try to find something in common. Whether it be work, extracurricular activities, history, people we know, where we grew up, places we’ve visited. When someone talks we immediately start thinking of ways we can compliment whatever they’re saying. This is natural, so use it in your favor.
  4. Listen more than you talk.
    You have to let her talk and you have to listen. If it gets long and windy, practice active listening. It’s really that simple.
  5. If you stumble, don’t have an answer, get tongue tied – deflect.
    Ask them the same question.  Once you get more practice with deflection, you can change up the words so you’re repeating them verbatim.If you’re nervous, and who isn’t, the biggest thing you can do if they ask you a question you don’t know how to answer or you don’t want to answer Just flip the questions around on them.

If you get nervous on a first date

If you’re worried they will be assessing you, looking you over, analyzing you, it’s going to build anxiety and other emotions that you don’t need. Emotions are energy. Energy can either be filled with anxiety and nerves; or it can be in the form of a settled calm. The more anxiety you project into a date that hasn’t even happened; stress will accumulate. Instead of putting anxious energy out there, make all that work for you. Turn your concerns into positive reinforcements because I want you to think healthy, productive thoughts about yourself going into any date. You are worth it. You are special. You have a whole lifetime of knowledge and experiences to share with someone.

Look at it sort of like a job interview

The way you go into any job interview is to prep. Put together a list of things you like about yourself … it could be a hobby, a sport, a project. If nothing comes up, then find a book and start reading it.

Now think about their potential questions. They might ask you: what do you do for work, what do you do for fun, do you have any trips planned…

Go ahead and answer those questions in your mind. Answer them in multiple ways. Answer them in the shower, in the car, when you’re putting away the dishes.

Align your traits with what might come up

You already have some things in common, such as where you met, how you meet, if you met on a dating profile what stands out, is there anything from your last conversation that rings a bell?  More prep work helps here. Jot the ideas down in your phone if you have to and look at it a few times before you meet.  

A few more first date conversation topics 

Think of something they might be interested in. Most of my escort dates were business men – they were into the news, stocks, science discoveries, medicine, etc. I don’t really care about stocks, and I know very little about medicine. But I did pick up a paper on my way through the airport and I had apps for National Geographic, BBC, Outside Magazine, Islands Magazine… pick a few and start creating a databank to pull from.

And one more conversation tip 

Ask her, how was your day? It’s simple. Its real. It shows the human side of you. And it leaves the door wide open.

Man and woman sitting at a cafe table


For first date conversations, try to avoid these topics

  1. Family, ex partners or exes of any sort
    It triggers emotions you don’t want to introduce on a first date
  2. Politics – strong opinions 
    These are important sure, you don’t want to waste time if you’re on completely different sides of the fence, but save it for the second date
  3. Very personal details
    It comes across as creepy and as being needy. Personal details such as finances, illness, etc.
  4. This isn’t the time for witty comebacks or getting in the last word
    Those are not good for first dates, second dates, probably not even third dates.

Sometimes less is best

Remember, you want them to want more. This is your goal. Don’t tell them your life story. You want them to come back and you want them eager to know more.





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