“There is an epidemic of boring in our society. And this plagues all of us.

Boring kills dates, networking events, sales and deals.

But, when we fight dullness we are more attractive, more memorable and more likable”. Vanessa van Edwards- the science of people

Our conversational skills are one way to avoid being boring and are often taken for granted and underestimated.  

They may be excellent in a business and professional environment and less so in social settings or vice versa.

You may be shy and introverted by nature and uncertain how to instigate an engaging conversation with someone new.

You may feel confident speaking with anyone, but don’t realise your topic and style of conversation is boring your date or people you are with

New York Times best-selling author and developmental molecular biologist, John Medina discovered that the brain has a very short attention span. Our brains are attracted to intriguing, interesting, engaging people and things.

Here are some simple tips to keep in mind when stuck for interesting ways to start conversations; to keep your conversations fresh, and show how engaging and interesting you are in social situations and in particular dating. 


Prepare yourself & know your Why

“Most interactions look like a flat line graph. You talk to people and it’s a dull conversation, what do you do? what brings you here?  There is no emotional jump or brain jump. So to stop being boring you have to cause more emotional excitement for the person. This is also more emotionally exciting for you and will help keep you more engaged”. Vanessa van Edwards

Without sounding rehearsed and as though you are attending a business interview or giving one; prepare yourself for a date with answers to universally interesting topics to start and keep the conversation flowing for both of you.  

Being ready with interesting light conversation triggers, and fun stories that help eliminate the awkward moments when you can’t think of anything to say after the factual, logical basics of where you work, live, where you studied, e.t.c have been covered. 

Some easy universal topics most people can engage in easily are

  •  How was your day? The answer can be a positive conversation starter. Many people fall into the trap of answering “fine” or “good” and stop there or might start complaining about the stressful day their work day was. It’s a great opportunity to share a small positive detail and engage. Find a positive aspect of your day and comment on that. 

  • Current trending news stories (avoid heavy and heated political, religious opinions) 

  • Favourite movies, music, food, holiday, book and why? 

  • Your hobbies and passions and why you enjoy them

  • Your life goals and dreams

  • Something you recently watched,read of that happened to you which inspired you or made you laugh out loud

  • A great place / event you went to recently which you loved and why

  • Classes you are taking or a project you are working on which you enjoy or find challenging

  • Your dream job if it isn't what you are doing now/ what would you love to be doing if not your current job

  • An accomplishment or achievement you are proud of and why? 

  • The most impulsive / spontaneous thing you have done. Was it good or a mistake? 

  • What are you looking for in a relationship? ( should be brief and light and no mention of bad relationships)

Another tip to get the conversation started is to be observant of your surroundings and to comment on the venue, the service, and the menu items and if you have been there before, and there is no harm in sincerely complimenting your date. As well as being character-revealing topics, they naturally build rapport, are fun, and make your date comfortable, which leads to a more interesting conversation and a deeper connection.  


“The quality of any interaction depends on the tendencies of those involved to seek and share attention. Competition develops when people seek to focus attention mainly on them; cooperation occurs when the participants are willing and able to give it.”Dr Charles Derber

To be engaging you should listen first and talk second. Someone has to start, so be prepared to. When you listen, stay relevant to the topic when you reply, don’t use your reply as a way to turn the conversation back to yourself- and conversation will flow naturally.   

There should be an equal balance of asking and revealing opinions, emotions and observations during the discussion.

Asking too many questions has the opposite effect, so does monopolising the conversation and talking about you only for the majority of the time you are together.    

The way to get beyond small talk and basic factual and logical conversation topics is to ask open-ended questions. Aim for questions that invite people to tell stories, rather than give bland, one-word answers. Essentially ask questions about what they find important- What has been the best part of your week? or what interesting plans do you have in the coming months?  Be prepared with interesting answers yourself too.

These kinds of conversations make you a good conversationalist while still learning about the person. 

Leading psychologist John Dewey discovered that

“One of the most fundamental aspects of people is that every person on this earth wants to feel important".

If you can make someone feel important by valuing their opinions, time or feelings, and being interested, YOU will be attractive and interesting to them.

If you are dating with a serious intention of meeting someone for a committed long term relationship, your energy and positive conversation style are worth showing more proactively using these tips to be attractive and intriguing.

Mature relationship- minded Singles are naturally drawn to people with more substance, which they can have a great conversation with and feel comfortable opening up to.  

If this is new for you, then without a doubt it will feel uncomfortable to begin with. It's worthwhile though, moving out of your comfort zone, and practicing these tips; at the very least you will have fun and interesting conversations and better connections which are never boring!  

Lots of Love 

Maria x




Would you like to learn how my off-line Matchmaking and Coaching service can help you connect to like-minded, smart, interesting Singles? Feel free to contact me for a no obligation chat.