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Flirting Woman Having a Texting Conversation. Using Conversation Starters.

30 Flirty Conversation Starters that You Need To Know

From funny jokes to flirty pick-up lines here are the best conversation starters.

Talking to someone you’ve met online can be a strange experience, especially if you are new to it. Unlike having a conversation face to face, messaging someone does not usually come as naturally, and conversations can fizzle out. Strong conversation starters can not only make your conversation last longer but make sure it is engaging too. When it comes to flirting over text, having a strong opener is the foundation of a long-lasting relationship. Here are 30 conversation topics that will help you make a great first impression and take your conversations over text to the next level.

Funny Conversation Starters

The best conversations are humorous and lighthearted, especially when you are meeting someone online. Humor is proven to make you more memorable, so why not use comedy to your advantage and stand out from the pack. Start your conversation off with one of these openers for laughs, and who knows where it will lead to.

1. What’s your favorite ridiculous fact?

Not everyone has a favorite ridiculous fact, but it will give you a good chance to showcase your own interesting strange facts. For example, Froot Loops are all flavored the same, or that a group of orangutans is called a congress. Conversations around ridiculous facts are sure to break the ice and give someone the opportunity to showcase their personality.

2. What’s your biggest pet peeve?

Everyone has something that annoys them, and usually, the thing that annoys us the most is very telling. It can also help you weed out people who don’t like things that you do.

3. Are you a fan of pineapple on pizza?

While this question may not give you any information on the person you are talking to it is a fun jumping-off point. There are very few conversation topics more controversial than the pineapple on pizza debate.

4. Is a hotdog a sandwich?

Speaking of controversial food opinions, here is a silly question with a lot of fun directions you take the conversation to. What do you think?

5. What’s your least favorite name?

Is there anything that bonds two people together better than making fun of something else? Making fun of names you don’t like is harmless and fun. Make sure you don’t pick the name of the person you are talking to (or their close friends and family)!

6. If you could be any animal what would you be?

Another fun question that may reveal more about someone than you’d first assume. Figure out why they chose the animal they chose and understand more about them as a person.

7. What’s your most irrational fear?

People don’t usually like sharing their deep fears and phobias, but irrational fears are less personal, and we usually are more willing to share them. If the person you are talking to does share their irrational fear with you make sure to share yours as well, and don’t make fun of them based on their fear. You want them to feel comfortable around you rather than judged or ridiculed.

8. If you could be on any game show what would it be?

This one is perfect for the TV junkies out there who would love to be on a reality TV game show. Find out their strategy for winning!

9. If you could have one superpower what would it be?

This one is a classic. There are the classics, of course, super strength, invisibility, flight, but try coming up with something creative and unique. 

10. What’s your favorite sitcom?

Whether you are a Friends fan or a New Girl nut, everyone has a sitcom they love. This line is especially effective if you share the same favorite show. 

11. What was your favorite show as a child?

Who doesn’t appreciate a little bit of nostalgia? Find out what shows the person you’re talking to grew up watching.

Flirty Pick-Up Lines

Flirting online can be especially difficult, and often it can feel like you have to choose between a cheesy pickup line or an awkward compliment. Not to mention bad flirting over text can all too often be boring. So, we’ve picked out some of our favorite flirty conversation starters that are sure to impress.

12. What kind of music are you into?

While this may not seem so flirty, it gives you an opportunity to listen to what they’re into and give your suggestions. You can even make them a playlist of music they would like. At the very least you’ll get a great music suggestion.

13. What does your perfect date look like?

Take notes! What are they looking for? Make it happen.

14. What’s your love language?

Love languages, from Gary Chapman’s bestseller The 5 Love Languages® is a cultural touchstone, and if the person you are talking to is unfamiliar with the concept you can always explain it. Knowing how someone likes to receive love will definitely come in handy down the line in the relationship.

15. Tell me something about you that would surprise me.

Don’t judge a book by its cover, so give the person you are talking to a chance to shock you.

16. Do you believe in fate/destiny?

Call it corny all you want but everyone has an opinion when it comes to the topic of fate that will let you gauge how romantic they are.

17. What’s your biggest dating deal-breaker/red flag?

When it comes to dating, knowing what a person hates is almost as important as knowing what a person loves.

18. Where should we go this weekend?

It may be bold, but sometimes that’s the best way to do things. Ask them out by assuming you are already going out.

Deep Conversation Starters

One of the best ways to start an interesting conversation over text is through asking a question. No, not “Hey, how are you?” or “How’s your day been?”, but something interesting, deep, a topic that will tell you a lot about this person. These deep questions are sure to result in deep conversations as long as you keep them interesting.

19. What is the most important quality of a successful relationship?

Finding out what a successful relationship means to someone else can help you determine what they’re looking for, and whether you’d get along with them. This question could be a little intense for an opener, so consider saving this one for later!

20. When do you feel the most like you?

Try to get at where and what makes them feel comfortable. Knowing when they are happiest/most comfortable will help you understand them better, and help you connect with them.

21. What does your perfect day look like?

Find out what they like to do. It’s deeper than asking about their hobbies or their interests because you’re getting at the heart of what makes them happy.

22. If you could go anywhere in the world where would it be?

Someone’s dream vacation/location can tell you about their ideal setting. Are they a city person? Do they like the beach? Maybe one day you’ll take a trip there together.

23. If you won the lottery what would you buy first?

Who doesn’t love the lottery hypothetical? You can learn a lot about what someone values based on how they’d spend their money.

24. What’s your favorite comfort food?

Sweet or savory, people love to talk about food. Make sure you take notes when you decide to make a date reservation!

25. Dogs or cats?

Pets can be a big part of our lives and relationships, isn’t it better to know if we’re dealing with dog or cat people right off the bat? Or perhaps someone that doesn’t like pets at all!

26. What does your alone time look like for you?

Everyone needs time to themselves, but what we do with that time may differ. Some take a nap others may go for a walk. Their answer may reveal a lot about who they truly are.

27. How would your best friend describe you?

Even though this question may seem a little interview-y, it can still be an interesting conversation.

28. What’s one possession you could not go without?

Bonus points if they answer this with something other than phone, wallet, or keys. Knowing what possessions someone values is important to get to know what they enjoy and how they like to spend their time.

29. What would be the title of your biography?

We are all the main characters of our own stories, and it is gratifying when someone acknowledges that in a fun and playful way.

30. What’s the best advice you’ve ever received?

If good for nothing else, at least you will get some good advice out of this conversation.

Conversation Topic Tips

Now that you know the 30 best conversation starters to use when talking to someone new online it’s important to know when to use them. Much like a normal face-to-face conversation you’re going to want to start off with normal greetings. It may seem strange if without any earlier conversation you ask about what TV show they watched as a kid or whether they believe in destiny.

Try to not use too many conversation starters in one conversation or it will start to feel like an interview. You do not want to overwhelm people with personal questions. Try to take a question you think they would enjoy and see where that conversation topic takes you.

As always, use your judgment. Natural conversations can start with a conversation starter but they should not revolve around them. Good luck with your conversations! For more advice on dating online check out our articles on the most common dating bio mistakes and the perfect photos for your dating profile.

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