Best Online Dating Conversation Starters - Cool Dating Advice

Best Online Dating Conversation Starters

With all the technology, social media, and dating sites we have nowadays, it is very simple and easy to meet someone online. It is very convenient for people to find out if they like someone before going on the first date. For those of you who have had bad first date experiences, you know that this erases some awkward moments.

Many times, couples are first introduced to each other on the internet. This is great because it gives you the opportunity to come into contact with someone you may have never had the chance to meet. With that being said, it is a lot different than going on dates in person. It is important to be able to show people who you really are while online dating. Here are some good conversation starters to get yourself off on the right foot when online dating.

Where are You From?

This is such an important question. It is vital to know someone’s life story before you get involved with them. This question opens up so many doors and opportunities to talk about other important topics. Some following questions may lead to talking about high school and college. Give them a chance to tell you about being the star of the football team, or crowned homecoming queen. People love talking about their glory days. Let them tell you about all their crazy drunk college stories, or about how they knew that college wasn’t for them. This question allows you to see the basis of why this person is who they are today. Your hometown and your childhood are so important. You need to understand someone’s past before you are capable of understanding their future.

What are Your Hobbies?

Asking about someone’s hobbies really gives you the chance to understand what they are passionate about. Some people do not have the same passion for their jobs as they do their hobbies, o this really allows you to get to know the person you’re talking to. You can also rephrase this question as “What do you do for fun?”. It is also good for you to know what this person spends their free time to do because if you move on in your relationship, this will be relevant to your life. Plus, this will help you find things that you have in common. Let’s say, for example, that you both love going to the movies or going fishing. This allows for the perfect first date to meet in person.

What Do You Do for a Living?


This question is important because, for those of us that have a job, we spend a lot of our time at work. This gives both of you the opportunity to explain your job, how long you have worked there and what it took to get there. It is interesting to hear the accomplishments that people have made in their life. It might make you look at them differently and appreciate their hard work.

Do You Have Pets?

Pets can be some people’s babies. Sometimes if you do not like pets, it can be a turn off for someone who is a pet lover and wants to have twenty cats, three dogs, and a rabbit for the rest of their life. It can also help you bond over your love for animals. You can send each other pictures of your animals at home and explain how your animals have had an impact on your life. You can even ask them “Are You a Cat Person or a Dog Person?”

Tell Me About Your Family

This is where things start getting personal. You can ask them about their home life and about their family. It is important to know what values are important to someone you are talking to. If you are very close to your family and are very serious about your relationship with them, that is something that you want to tell the other person. This allows for you both to be able to tell good and bad stories about members of your family. Ask about their parents. If you end up dating in the end, you will meet these people, and it is important for you to listen to their characteristics and hat they are like so that you can make a good impression.

What Kind of Music Do You Listen To?

You can tell a lot about a person through the kind of music they listen to. Music is such a big part of our everyday lives. This allows both of you to talk about your favorite artists and songs. You can even start talking about what concerts you have been to and how your music taste has changed over time. If you find that you have favorite songs or music in common, you can talk about this in the future, or remember it for when you start going on dates in person. People like when your ember the little things.

Do You Like Traveling?

Nowadays everyone is always traveling somewhere. I don’t know about you, but I love hearing stories about all the magical places that people have visited. This gives you both the opportunity to tell stories and get to know more in depth about each other’s lives. If one of you has not really traveled anywhere, you can talk about all the places you would like to go.

Tell Me About Your Friends

You can tell a lot about someone by the people that they surround themselves with. Friends are always going to be a major factor in any relationship, and it is important that you talk about what you are like with your friends. You also want to make sure that they do not hang around with troublemakers or bad influences because that will affect their behavior. This can also show how compassionate this person is. People who treat their friends like gold will treat you like gold too.

Do You Like Sports?

Sports are huge factors in some people’s lives. You can talk about what sports each of you like and what sports teams each of you root for. You can also start talking about what sports you used to play. This is another good question to start finding out what you have in common with someone. If you like the same teams, you can plan to go cheer on your favorite team together.

What is Your Favorite Book and Movie?

Just like music, you can tell a lot about the person by the kind of movies they watch and the kind of books they read. If they love dramas and romantic movies, then they are a hopeless romantic. You can also tell how intelligent they are and learn a lot about their knowledge and what they find interesting. This can lead to so many good conversations about other things and other favorites and is always a great conversation starter. Let people talk about their interests, it opens up doors to talk about anything.

What Are You Looking for in a Relationship?

It is always important to keep each other’s goals straight. You want to make sure that you are on the same page and know what you would want out of furthering this relationship. Some people get uncomfortable asking these questions, but it actually shows the other person that you care and that you want this relationship to actually go somewhere. It gives them reassurance.

Ask for Advice

If you really want to show someone that you want to know their opinions, and you care what they think, it is always great to ask for advice about other things in life. What should I wear to this job interview? What should I tell my friend about getting back with their ex? This will also show you how they would react in certain situations and you can learn a lot about them as a person.

What is Your Schedule Like?

It is important for you to know when the other person will have time to talk to you. If you need a lot of attention, someone with a busy schedule will not be good for you. This is always a good question because you get to ask about what someone’s everyday life is like. You can also talk about your schedule and how you believe you would be able to fit this person in your life. That will show them that you are willing to compromise.

If you could live anywhere, where would it be?


The next three conversational starters are more interesting and fun questions. Sometimes you ask a fun question you get some really fun answers. These types of questions will really allow you to see what type of person is on the other end of the messaging app. Maybe they say something like,”I am never living any place but here.” That just tells you they are maybe a home body and like to stay local. If they say I would live in Paris or Hawaii then maybe you have a more adventurous soul.

If you could be a character in any movie, who would you be?

This is another fun question to see what kind of response you get. Maybe they want to be a super hero or play a detective. No matter what they say it will lead into some good conversation online.

What’s one thing you’d bring with you to a deserted tropical island?

One more fun one does not hurt when talking online and starting a conversation. I was just thinking what would I bring to a deserted tropical Island. The thought I had was survival gear so you can get purified water and food. Other people may not think of this as a setting of survival so they may say a lounge chair to sun bathe or a 12 pack of beer. The answers will give you some insight into the person on the other side of the dating site.

Overall, just make sure that when you start talking to someone online, you get to know them well. There is an endless number of good topics that you can take about, but it is important to hit all the bases. Sometimes it can be harder to gauge someone’s opinion through texting or messaging, so don’t be afraid to ask a lot of questions. Online dating can open so many doors, so make sure you get the most out of it. Don’t be afraid to ask crazy and specific questions. Most people love when other people are deeply interested in their lives. If you happen to go on a second date check out are article on Dating tips for the second date.

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