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How to Make Conversation on a First Date

How to Make Conversation on a First Date

How to Make Conversation on a First Date

Hi Guys, it’s Emyli again. I want to tackle how to make conversation on a first date. Have you ever been on a first date where the conversation came to a halt? Neither one of you know what to say; you’ve exhausted the few topics you had prepared. The date becomes awkward and cringe worthy.

I went on date after date during my 100-date experiment, which led to the launching of my site to help single people reach their dating goals. I learned first hand, how important engaging, interesting, and genuine conversation are. I want to teach you how to make conversation on a first date, so your first date can turn into a second (if you want it to).

Conversation can be easy if you just met, when you’re still learning the basics of one another, but I’ll also go over what to talk about on a first date with someone you already know. I’ll help out with some first date questions you can ask. Dating is an art, which you can master. It requires planning, research, and the right mindset. I’m your coach, and you can win this game!



How to Make Conversation on a First Date: What You Should Talk About

The conversation on a first date explores initial compatibility and interest. During this first date, you both will be taking in every scrap of information, like little puzzle pieces to try to put together a complete picture. The setting of the date is very important, if you’re in a loud environment, talking may be difficult. First read these tips for planning a first date.

The conversation on a first date is going to be a little different with someone you just met compared to someone you are already know. A first date with a stranger is going to require asking some basic first date questions to get to know them. On a first date with someone you already know, you’re going to want to do a quick catch up, and then you can dive into some deeper subjects. 

Really Listen

You aren’t listening if you are on your phone, talking over the other person, not making eye contact, or drifting off during the conversation. Your date will notice this behavior. Women can tell when someone isn’t paying attention or interested in what they have to say. Use these first date questions to get to know your date and show her that you are truly interested in her. If she answers one of your questions, don’t be afraid to ask another one based on her reply. The deeper you get in a single thread of conversation, the better!

At the end of the day- if you aren’t listening, you’ll continue to wonder how to make conversation on a first date. Sometimes it can be hard to listen, and it’s not necessarily your fault. This submitted question from a client (and 3 answers from me) of mine falls into this category:

Q&A About Listening From a Client

Question: What should I do if I take my date to a social bounce location and it seems like we are pretty much ignoring one another?

Answer #1: Ask questions until you see their eyes light up, then ask deeper questions about that same subject. Avoid superficial conversation, really make your questions meaningful. This will get your date to open up to you.

Answer #2: Another hidden problem is that you have not established enough trust for your date to feel comfortable enough to open up. This could be why your date offers only limited responses.

Answer #3: Try to stimulate the engaging side of the person you are with. All women are talkative, our brains have a much more active verbal control center than men so we are hardwired to want to talk. All you have to do is build enough trust so that she feels that she can tell you things. Use vulnerability to stimulate this as well!

Keep it Positive

You want to be as positive as possible during your date. Don’t forget, first dates should be no longer than one-hour in duration. This one-hour period is all your date will have to form an opinion of you. If you’re on a first date with someone you know, this will be your chance for her to see you in a different light, you want to talk positively.  

It may feel unnatural but keep in mind that during a date every question and response becomes magnified. Your bitter comment may have been harmless to you, but to them it was a red flag about your personality. Keep the sarcasm and negativity to a minimum. If you say too many negative things, your date will assume your life is depressing. No one is looking to add more negativity and depression to their life. Women are looking for someone to add happiness and positivity and not bring them down.

Paint a Picture

The first date is an initial taste of who you are and what your life is like. You want to paint a picture of what every day life would be like with you. Highlighting less pronounced aspects of your character, like going to sporting events and concerts, is like giving them paint to color in the lines. You want to give subtle hints of fun things you would do together to make your date want to share a life with you.



Talk about how you like to cook, draw, garden, or go to museums. If you’re on a first date with someone you already know, talk about the hobbies and things that they don’t know about you. Surprise them with these details that will help shape their perception of you.

What Not To Do: Conversations To Avoid

During the first date, the person you are sharing time with will create an idea of who you are. They will form opinions based off of the conversations you have. If you’re on a date with someone you already know, you’re a little ahead of the game because chances are they already have a positive opinion of you, or they wouldn’t have agreed to go out. If you’re boring on the first date, there will not be a second.

One of the biggest mistakes you can make on a first date is talk about your ex. Your date will assume you are not over your ex or have some hang-ups about your break up. If you’re on a date with someone you already know (and they know about your ex) keep it positive. Hating on your ex will make you look like the one with issues. If it happens to come up, keep it short and sweet then move on to the next topic.

Avoid Taboo Topics

This is one of my favorite how to make conversation on a first date tips. So much so, that I dedicated an entire blog and video on avoiding taboo subjects on a date-because it’s so important and can easily be a buzz kill on a first date. There are certain things that are better left unsaid on a date. Try to avoid topics of sex, violence, anything grotesque. If your job involves one of these topics, don’t go into a lot of detail. These topics can trigger a fight or flight response in your date and make them guarded and judgmental. If you have to ask, it’s too soon.

Don’t Talk About Work

Replace any detailed conversations about work with hobbies and interests; they are more fascinating and reliable. Do not use work-related jargon in an attempt to impress your date. Highlighting your hobbies and interests will show your date you have a great work-life balance, and that you’re not a workaholic. And most definitely never talk about how much money you make. That’s never OK. Here at EmLovz we don’t support gold-diggers! 

Don’t Talk About How Great You Are

If you’re starting every sentence with “I,” then you are definitely doing something wrong. You want to practice the “show me, don’t tell me” philosophy. Use stories to highlight positive characteristics about yourself. I go over in this video how to use stories to highlight your value. Don’t overtly state “I’m nice,” “I’m smart,” “I did this…” let the stories speak for themselves, and let your date reach their own conclusions about your character.

Definitely don’t to seem self-absorbed either, ask your date questions about themselves. If you realize you’re the one doing all of the talking, take a step back and ask them some questions. Here’s another question from a client of mine on this topic: 

Question: What should I do when my date gives me only short, non-narrative answers that make the conversation feel like an interrogation?

Answer: Acknowledge that to some people, it is normal and comfortable for them to be passive. Make it your job to create interesting dialogue. Even when people are giving you very little to work with, you can still find something to spark their interest.

Want More Conversation Tips?

The first date is important for forming initial opinions and deciding if there is enough attraction and compatibility for a second date. There is a lot at play with a first date. Here are some first date tips I complied during my 100-date experiment that will help you get to a second date. Want me to pump the brakes because you are still struggling to get first dates? Check out some of my recommendations for the best dating sites for men



It is important to keep your date interested, intrigued, and wanting more. If you’re boring, negative, or talk about any taboo subjects, you are going to have a hard time getting the second date. If you’re feeling uneasy about a first date you have coming up, I am available for an intro Skype session for only. Head on over to my calendar to book a session. This is the perfect opportunity to go over any specific questions or concerns you have. I love working with smart, hardworking men who are looking to find a girlfriend, wife, or long term partner. 

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