How To Be A Great Conversationalist When Dating


So you met someone you like or you’re on a date and all of a sudden you run out of things to talk about. As you sit shifting in your seat uncomfortably, you are trying to find something, anything, to talk about. You just want to leave. Does this sound familiar? You wonder why with some people conversations come easy, while, with others conversations are torture. It’s all about communication skills, some people are just better at it than others. I work with a lot of clients who, while they are brilliant at what they do in life, they have a lack in communications skills. Being a good communicator starts with being a great conversationalist. What that means is being able to capture someone’s interest and attention with what you’re saying. Engaging them and keeping them interested. Have you noticed all those charismatic men and women who seem to always have everyone’s attention even if they’re not attractive? THEY are great conversationalists – they don’t play hard to get they ARE hard to forget. Read on to find out how to be a great success!

How To Be A Great Conversationalist When Dating

Be Resourceful

Be knowledgeable about current affairs and what’s going on in the world. You should always have an interesting topic under your belt, even if your day to day life is pretty mediocre. I’ve mentioned before that there are several websites that talk about current affairs and fun facts. Google NewsFlipboard and Mind Body Green‘s things you need to know today. I get my clients to learn something new every day and to be prepared to talk about it in minimal time. Don’t talk about yourself unless you’re talking about what you’re passionate about or something you’ve done that’s interesting AND even then be able to explain it in a few lines or less or else the other person will get bored. A good idea is to use your surroundings as a conversation starter, talk about what’s going on around you. Always be ready to talk about anything going on in your town as well as the world, so be up to date with facts and your opinions on the issues that are trending.

Ask Questions

In order to show that you’re engaged and interested a conversation has to be a lot of “give and take”. Also, let’s be honest, people love to talk about themselves and talk to people who are interested in them and their story. Questions you should ask is about their interests, hobbies, something fascinating about them, what they’re passionate about, what makes them happy or what gets them riled up. Keep it simple but not boring with the usual standard “where you’re from” “where do you work” questions. By asking interesting and different questions, you can determine common interests and introduce some interesting conversation topics based on things you both like to discuss. That “give and take” creates connections and the more engaged they are in the conversation the more interest they have in continuing conversations with you.

Be a Good Listener

The other part of that “give and take” is, of course, being a good listener. Being a good listener is about actually hearing what the other person said and being able to paraphrase it as well as asking follow-up questions. It creates a flow of back and forth that’s natural and interesting building up to your desired result, whether it be a number or to see them again. When you are an effective listener, you also learn a lot about that other person which allows you to suggest potential activities you can do together based on their interests. For example, if they talk about how much they love museums you can (because you were already resourceful about what was going on in town) suggest going to see a new interesting exhibit that just opened. See what I just did there? You not only demonstrated that you were listening but you also demonstrated common interest and a potential date they would find hard to refuse. Listening is about body language as well, remember to make eye contact, nod your head and show that you’re paying attention to what they’re saying.

Use Humor

Being light hearted and finding humor in common situations is a very valuable quality to have. This doesn’t mean telling jokes or making fun at other people’s expense. It means demonstrating that you don’t take life too seriously, that you’re not a stick in the mud and that you like to have fun. Be witty and in your “resource prep” make sure to have some funny stories under your belt, even if you’re laughing at yourself. Nothing dirty or “off color”. If they use humor (that you don’t find offensive of course) then laugh and maybe share a similar experience. Laughter lightens the mood and makes people more open and increases your likeability factor by a large percentage.

Give Compliments & Be Gracious

Tell me who doesn’t like receiving compliments BUT NO ONE wants to receive insincere compliments. If the person you’re speaking with says something interesting or made you think of something a different way or even made a good point, then tell them. If what they’re wearing looks good on them tell them but in an appropriate way … for example, say “that outfit looks great on you” or “I love the color of your hair”. Did they choose a delicious wine for your date? Tell them. Congratulate them for any accomplishments they mention in their conversation as well. Compliments should have no goal end in mind other than to appreciate the other person in some way. Always thank them for the time they spend with you, even if it’s only a few minutes and if you enjoyed your time mention that you would appreciate doing it again sometime.

Being a great conversationalist is about showing that you’re comfortable in your own skin and that you’re not afraid of being yourself. Meeting people should be just that, meeting people. If something comes out of it great, if not, then that’s OK, at least you had a great conversation! Remember, being hard to forget, keeping them engaged and interested will get you to your goal. Even if it doesn’t come naturally to you, each and every one of us has a great conversationalist hidden inside them. If the whole talking to strangers thing makes you nervous, start by talking to service staff such as baristas, cashiers and waiters. Slowly work your way up to people waiting in line with you and then people in the same places as you. One step at a time and you will reach your goal. Now, go forth and TALK!

READERS: Do you get bored on dates or do your dates get bored with you? Share your thoughts in the comments below!

Your Sister in Dating Bliss,

Single Dating Diva

Copyright Single Dating Diva
Reproduction of this page whether whole or in part is completely prohibited. Please use the contact form if you would like to discuss using any content on this site


  1. Great advice. I struggle with this a lot because I watch what is going on in the world but sometimes it becomes a struggle to not offend someone.


  2. These I great advice. I have to admit that I am not good in starting conversations when I meet new people and I always wait for other person to speak first. I don’t want to say something that might come out offending to the other person. 😦


  3. All really good advice. I also read when meeting new people you should use “the swiveling spotlight”- basically focus most of the conversation on the other person as most people like talking about themselves!


Comments are closed.