30 Flirty Conversation Starters that You Need To Know for Online Dating

Let’s face it:

Online dating can be rugged and tricky. Even if you find someone you are interested in, the ice-breaking moment is often the most challenging.


Coming up with deep or flirty questions to talk about can be difficult and frustrating.

It’s not easy to speak with someone you don’t know well. Unless they are your friends or colleagues, most people feel awkward talking about something that interests them in another person. It can be even more cumbersome to come up with a list of questions, to catch the attention of a potential partner. 

According to a study by journals.sagepub.com, flirting is essential for online dating.

Flirty and funny questions are the secret ingredient that makes your message stand out from others. Everyone wants to meet someone special, but only those who ask fun questions can achieve their goals. 

A cheesy pick-up line will help you leave an impression and make them want to chat with you again or even more than that! So, how do we start a flirty conversation in an online dating profile? We know some ways to help you get started. 

In this article, we discuss:

  • The 30 flirty conversation starters to help you ace online dating 

The 30 Quirky and Flirty Conversation Starters To Help You Get Started

1. Mention something you like about their looks

When starting conversations on online dating, initiate with compliments. Flattery and compliments are the best displays of affection, especially during the beginning of a relationship. The dating game is a tricky one, so make sure you're not just throwing random questions at your potential match.

Whether their smile, eyes, or hair, mentioning a physical feature you like about their looks makes them feel good. It is easy to break the ice and make them feel good about themselves.


2. Talk about your preferences

It’s also a flawless way to spark a conversation about the kind of people you both like.

For example, ask fun questions about goals, dream jobs, plans, interests, hobbies, and more. This way, you can find the common point between you and the other person. 


3. Examine serial dater/one-time dater

If you don’t know how to approach them, ask them if it’s their first date or are they pursuing other people.

If they have only dated once, you can ask them why they didn’t go on another date. If they are serial daters, you can ask them how long they date each person. These flirty questions will give you an idea of how serious they are about their dating life.

Learn Also:


4. Ask if they have any hook-up ties

When you ask someone if they have hook-up ties, they will most likely talk about their preferences in bed.  So, if you are looking for a serious relationship, this is an excellent way to weed out sexually aggressive people. Hence, it is a basic question and definitely needs to be on your list.


5. Quote a funny message or conversation from your last date

When you quote a message from your later date, you can also tell them about your views on dating and relationships. This is a great way to show that you are an interesting person. But avoid dad jokes as those can come off as being a little lame.


6. Ask if they’re an early riser or a night owl

When you ask personal questions like: “Are you a night owl or early riser?” you indirectly ask them about their sleeping habits. This is an excellent way to know what kind of person they are.

These personal questions will help you understand their sleeping habits and behavior.


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7. Ask where they like to hang out

When you ask deep questions about hanging out, you indirectly ask them about their interest and travel bucket lists. 

If they like to go to places you hate, it’s best to avoid them. If they want to go to places you love, it’s best to pursue them. You can also ask him/her about their favorite food - you'd be surprised to know that food is a guilty pleasure for many and often the start of many deep conversations.


8. Comment on their profile

If you’re unsure how to start the conversation, start commenting on their profile. That can be anything related to age, gender, profile picture, rating, etc.

When commenting on their looks, try a unique approach—for example, asking about the location in the background or the name of the pet the person is holding. Look for something extra or particular to begin with.

9. Ask them about their day

If it’s night, ask personal questions about how their day went. If it’s morning, ask them how they’d like to spend the day.

This way, when you talk daily, you’ll be able to notice if they fulfill their goals or bucket list along the way.


10. Share a funny story

If you’re unsure about a funny story, go to the Google search bar and search for funny stories or riddles. Select the one you like and start an engaging conversation.

You can also share a funny memory that happened to you.


11. Ask if they have any pets

The most romantic way to start a conversation is to highlight pet animals. If they have one, ask the pet dog's name and breed.  This way, you can show interest in the other person.


12.  Ask the meaning of their name

If you’re looking for the cheesy pick-up line to start a conversation, ask the meaning of their name.

Let’s take the name is John, to which you reply, “Oh wow, such a cute name; the meaning should be handsome. It suits more.” And then you can lead with deep conversations, to deepen the relationship.

13. Talk about famous brands

Give them options to select from, like “Are you a Polo or Ralph Lauren fan?” If they supposedly reject one, ask if they had any bad experiences.

This way, you can have a leisurely chat forward and refer to the previous question to keep the conversation going. It doesn't take a relationship coach to come up with such ideas!


14. Talk about something you have in common

Pick personal questions and talk related to them. If they’re engaging in going to the gym, ask them if they’re gym freaks or wish they were.

Let them talk about their interests...and if you are feeling a little bold, you can turn the common ground into cheesy pickup lines to really show how you feel.


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15. Mention a book or movie character they resemble with

If you want to start with an idea to penetrate deeply into their thoughts, they tell them how their character matches Michele Morrone from 365 days.

Or, go with any other movie you like.


16. Ask if they like to travel

Begin with asking if they plan to travel this summer. This way, you’ll get an idea about their travel bucket list and if they also want you to tag along.


17. Share pics, emojis, or gifs

If you’re afraid to send a message, send them a “wave” emoji instead.

Let’s see how they respond. If you’re shy, try sending your messages through gifs instead. It makes a huge impact!


18. Pluck a rose and send the image

If you live near a garden, go and find a dropdown leave/flower from the ground. Send the picture to the person as a good and casual gesture.

You can also do this trick by sending an image of anything you’re doing.


19. Ask if they have used any dating apps before

Don’t be shy and ask if that’s their first experience using an online dating app. Tell me how it’s the first one for you.

This immediately gives you a chance to appear innocent, cute, and submissive.


20. Talk about likes/dislikes

For example, start with why they have particular likes and dislikes and how it can bring flavor if you both merge.

This way, you tell a problem and give a solution. You can also ask flirty questions at this point.


21. Ask for their life story

For a bright conversation starter, ask the person, “What makes you special and unique?”

Just type this and let the other person impress with their life story and challenges. Everyone loves being challenged1


22. Play games

If you’re bored, invite them to a game such as a ludo star or eight-ball pool. Later you can talk about yourself in the chat while playing the game.

Sounds impressive.


23. Mention your family

You can also ask if they belong to a particular area or are immigrants. This is a great way to know about someone, their caste, and traditions.

Also, a heads up before you engage with someone.



24. Ask if they like somebody/are heartbroken

If you see anything dismal in their profile, reach out and ask that you’re happy to help. Ask them to share if they had a bad experience and how you can undo it.

Partners like to feel secure.


25. Ask what their ideal partner is like

Start with “Okay, so, what are some ideal qualities you’re looking for?”

This may look like a corporate, personal question, but it has more rates of melting someone’s heart. These are the flirty questions for professional dates.


26. Ask them about their dream job

Everyone has strong opinions about jobs. Ask them about what their dream job sounds like.

This is an easy starter right at your fingertips.


27. Offer them to connect.

If you’re afraid to start a conversation on a specific dating site, take them to a different platform such as Facebook or Instagram. These social media platforms have the power to make online dating easy-going and friendly.


28. Talk about a celebrity

To make a causal starting, ask about their celebrity preference. A good start can be about Amber Heard vs. Johnny Depp or Bill gates vs. Melinda gates.


29. Talk about the weather

If you live in the same area, talk about how the weather is uncertain. If you live in different places or regions, introduce them into your life and the weather causing problems in your daily routines. Share about your life.


30. Ask them to share a picture

Ask them: what are you doing? Start sending pictures and make them feel connected to your presence.

Next thing you know, they’re already impressed by you. 

Summing up:

If you’ve signed up for dating apps, have your profile photo taken with good lighting; you now need flirty questions to start to impress the other person.

Remember that the first impression is always the best one. And in online dating platforms, deep questions leave an impact.

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Now, over to you....Was current post useful? Do you know any Flirty Conversation Starters that can be effectively used for Online dating?  Feel free to share your opinion on the subject I have described above and kindly leave your comment bellow.

Written by Katrina El, a practicing psychologist, professional matchmaker and founder of the Slavic marriage agency Best-Matchmaking.com.

Learn more about the matchmaking service by Best-Matchmaking.com

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