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Relationships Thrive with Great Conversations

Having great conversations is the foundation to all relationships, both personal and professional.

Which is why making a conversation interesting is so important. To be a great conversationalist you have to be first and foremost a great listener. Every person is made to feel important by being listened to and asked about themselves.


People LOVE to talk about themselves, so let them!


By being a great listener you are able to find clues about the person that can be used for further conversation starters. By showing interest in the other person they will start to feel comfortable in opening up more and starts to build trust.


You may find yourself in a conversation that you want to correct them and let them know where or how they are wrong. Contradicting people doesn’t build relationships. You have to know when and how to bring your contradictory opinions up to others. If your main goal is to connect and build trust you should hold off until there is a foundation first.


Asking questions shows that you have been listening. Studies show that by showing interest you will become more likable. Active listening requires that you do not interrupt and when appropriate  repeat back the main point they are making.


Great questions to ask would be to reflect on what was already talked about briefly and ask for more details. Another great way to make a good  impression is to ask advice this encourages greater cooperation and information sharing.


How to start a conversation


Starting a conversation, depends upon the situation. Networking situations are different than a serendipitous conversation with a stranger. The key to both is to keep it light.


While you may feel intimidated, remember that no one should have that much power over you. Some good communication tips for each situation are listed to confidently break the ice. Just remember to greet them with a smile & keep the initial meeting casual and friendly.



-Ask questions or Give an honest compliment


-Let them talk about themselves

-Ask open ended questions

-Sharing your own experiences can create meaningful conversations

– Showing vulnerability helps build trust

-Saying OK, really? that’s interesting! Huh… these move the conversation forward

 Don’t be thinking about a response which keeps you from really listening and paraphrase what  has been said.

– Ask for advice (builds trust when networking)



People LOVE to talk about themselves, so let them!


How to Start a Conversation with a Stranger


The easiest way to start a conversation is to ask a question or give a compliment. Both allow the other person to talk without having their guard up. Another easy way to have a conversation with a stranger (in a non networking environment) is to let them know that you only have a short amount of time to talk.


Let them know that you on your way to meet friends etc. This overcomes the initial hesitation and makes the conversation less intimidating.The person that you are talking to probably will be more open to a quick conversation. It can be very charming to say to someone “I know this is strange, but I will regret it if I don’t try to talk to you.” Followed by “Hi, my name is…..”


If she/he is showing interest you can then follow up after the initial meeting by asking for their number. These communication skills will help you when you are networking or when first having a conversation with a stranger.


How to Make interesting Conversations with a Girl or Guy


I think we put more emphasis than is necessary when we are talking with a girl or guy. The same basic rules apply to all conversations and require the same effective communication skills.


If you are trying to make a good impression than an honest compliment will be a nice way to break the ice. Asking an appropriate question that fits the setting will also create an easy way to  start a conversation.


Keep the conversation light and casual. Showing genuine interest in another person is attractive. Use their answers as a jumping off point to keep the conversation moving.  Some great ways to start a conversation includes conversation topics such as their likes in music, movies & travel.


Asking someone their favorite band (or place to travel) keeps things light and gives a little insight into their personality. Hopefully you will be able to move on to more meaningful conversations as you get to know them better.


First Date Conversations


The goal is to get to know this new person so do not talk about your exes. This is especially true if  the talk is negative. There is a good possibility that if you do, it will come off that you are not over your previous relationships.


Keep the flirty conversations until after you get to know them better, since it is very easy in the beginning for things to be misinterpreted. Bringing up some upcoming events that you are interested in can help move the conversation to see if there is interest in a second date.


How to Have Meaningful Conversations


Telling personal stories about yourself builds a greater connection between you both. You can make others feel special by taking the time and asking questions to understand what their needs, wants & dreams are. Talking about their interests makes them feel important if done sincerely.


interesting conversations


Becoming genuinely interested in other people will help you create more meaningful conversations. Remember to smile and make eye contact when talking. People love hearing their name, make a point to sprinkle their name into the conversation.


Be a good listener and encourage others to talk about themselves. Showing vulnerability or talking about your fears will create more in depth conversations. These communication skills will help the strengthen the bonds that you are creating.


Everyone needs to feel understood, appreciated and special


How to Have a Conversation  in a Text


Texting someone you know is VERY different than texting someone you do not know very well. You have to surmise what they meant and the tone in which they meant it. This opens up the opportunity to screw up or misunderstand the message. That is why it is so important to be as clear as possible.


We ALL have texted someone and were so surprised how different they acted or talked in real life vs how they were texting. People are more open to saying things, they would NEVER say in person. This is usually not good, make sure whatever you say in a text you would say in person. You have to be very careful with sarcasm or flirting in a text.


It can be confusing when the other person doesn’t know how you meant the message. The safest way initially is to keep your texting as clear as possible.


OK that being said, do not just say “Hi”,  to start a conversation you have to be more inventive than that! Btw, if you text in all caps, that is the equivalent of yelling and keep your exclamation points to a minimum.


Asking open ended questions will help get rid of the one word answers and keep the conversation going. Pay attention to the natural flow of the conversation. Make sure that you are clear if you need to end the conversation. “I have to head out, hope your day goes well” or “I have an appointment soon, so I’ll talk to you later.”


Be careful when texting…


Be polite and text similar to your talking style. It is a good Idea to mix it up with phone calls, you can learn much more about a person and will help in future texting conversations.


The great thing about texting is that you can send a quick text, when you want to share a funny moment in your day. Those moments help to keep you connected, when you can’t have a full blown conversation.


Just be aware of ques that the other person if giving. The conversation should be a give and take. If you are doing all the texting, that should tell you something. They either can’t talk or are not as interested so don’t text as much.


This is when a phone call can clear up that uncertainty because you can hear the tone in their voice. It will be easier to hear if they are excited to hear from you are acting disinterested.


If your goal is to date this person, then stop texting and ask them out! Also if you ask someone to hang out, they have no clue if that is a date or a friend thing. Have the courage to just ask them out on a DATE and set a time and place.



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Conversation Starters


Obviously the question you ask will be determined by the situation…so choose accordingly!


-So, who do you think should make the first move? The girl or the guy? (cute smile)


-Do you know where the closest gas station/coffee shop is?


-I can’t believe the sun is actually out today! Its seems like forever…


-I am looking for a bakery around here, do you know of one? Great question because, well you get the directions to a bakery!!


-What type of books do you read?


-Are you a foodie? Have you ever had anything really surprising?


-Do you like to cook?


-Where is your favorite place to travel?


-What is the best thing about traveling?


-Do you like musicals?


-What are your guilty pleasures?


-What are you passionate about?


-Do you have or want pets?


-What’s your favorite holiday?


-What is your favorite season?


-Do you like sports? What teams? Do you play?


-Favorite concerts that you have been to?


-Are you close with your family?


-Do you believe in Aliens?


-What are some things on your bucket list?


-Have you binge watched anything on Netflix?


-Do you have a favorite comedian?


-What are your craziest fears?


-Do you ever wish you were alive in another time period?


-What do you usually do when hanging out with friends?


Conversation Topics


Once you get past the introduction, you can dive into some interesting conversation topics. You will want some insight into their personality so there are many ways to get some clues.


What makes this person tick? What excites them? Where do they get inspiration? How do they spend their time? It boils down to being interested in them and finding ways for them to open up about those subjects.


What if your conversation stalls?


Have you ever been to a gathering and were bored to death? It can become monotonous to get ask the same questions, “What do you do? “Are you married.” It’s not that these are bad questions, it’s just that sometimes they don’t go very far and the conversation stalls.


Asking open ended questions that are more thoughtful can help.  I do believe that everybody has something that they are passionate about, but sometimes it may be hidden. A good conversation starts by being curious. Asking interesting questions can help to uncover more insightful information that will make your conversation interesting such as…




This should incorporate not only where they have been but where they would like to go and why. Have they been somewhere that they were surprised by?


What were their favorite discoveries? Maybe they like a tour better that exploring on their own, finding out why can be insightful.


Do they like to go hiking on trips  or would they rather lay on the beach? Most people have had experiences with traveling and it’s a great go-to conversation topic.




What have they done that has given them joy or what is one of their goals to do in the future?  This topic can tell you a lot about a person. Where they are and where they want to go. Maybe they want to write the great novel or be a digital nomad or train for a marathon.




So many people are passionate about their teams, whoever they are. Or maybe yoga or cycling is their thing. Many people spend a fair amount of time with the sport or exercise of their choice. This topic is usually a great one to explore.




 School, college, online classes. So many people have a love of learning and are in the process of getting degrees or just taking classes out of enjoyment. Book clubs are very popular and surprisingly physical books are being published at a fast pace even in this digital age. Find out what they love to read and this will give you many more topics to explore.


Having interesting conversations is not difficult when you follow the tips and topics that are listed. Of course you are trying to find commonalities between the both of you. People love to talk about themselves and feel special when someone cares enough to ask.


You will create the start of a relationship by just being curious and friendly

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