The Best Flirty Conversation Starters

Dating 101
27 Apr 2023
10 min read
Great Flirty Conversation Starters

When it comes to finding someone attractive, starting conversations can be a bit of a challenge. After all, you may become nervous, stutter, or even lose track of ways to talk. It may be hard to say a single word, not initiate an entire flirty conversation!

However, this does not mean you don’t stand a chance with them or you’re incapable of flirting. You just need to refine those flirting skills! They will get yourself to a level that makes you feel comfortable.

With this in mind, we’ll discover what you should do and say when you are flirting with someone. You’ll see some of our favorite pickup lines and conversation starters, and of course the types of pickup lines that should be avoided at all costs.

22 Pick-Up Lines and When to Use Them

There are many different types of flirty conversation starters, from the occasionally horrible pick-up line to the flirty texts that lead into deep conversations about life. Here are some of the different types of flirty pick-up lines, depending on your mood and flirty conversation situation. Get ready to land yourself a first date with that cute girl you are so into!

Generic flirty conversation starters

Generic Conversation Starters

  • What’s your favorite comfort food?
  • What is your biggest pet peeve?
  • Do you prefer dogs or cats?
  • If you won the lottery, what is the very first thing you would do?
  • What is your most controversial opinion?
  • Where was your first kiss?

These topics aren’t exactly what you would call a flirty conversation starter – however, we all have to start somewhere. These flirty conversation topics are such a delight as they let us get to know one another in a more comfortable sense. After all, it’s much easier to ask someone a generic question than invent an impressive pick-up line and hope that it simply doesn’t flop.

Funny flirting conversation topics

Funny Conversation Starters

  • How would your best friend describe you?
  • What is your favorite ridiculous fact?
  • What is your least favorite name?
  • What was the worst purchase you have ever made?
  • What is the craziest thing you have ever been afraid of?

It is commonly said that the best way to get someone comfortable around you is to simply make them laugh. So just do it! You can  use these funny conversation starters to catch the moment and get them to open to you.

Deep flirty conversation starter

Deep Conversation Starters

  • Tell me something about you that would surprise me
  • What’s the best advice you’ve ever received?
  • What is your biggest deal breaker?
  • What would your most perfect day look like?
  • What is your most prized possession?

Not everyone wants to answer a simple fun question. At times, your reply to a joke can send a series of mixed signals and cause misunderstanding, or the joke itself may sound insulting. On a contrary, a good conversation starter should open a door to discuss things that hold deep meaning to you both – secrets you have, topics that bother, or a new topic everyone talks about.

Romantic flirty pick up lines

Flirty and Romantic Conversation Starters To Ask Her Out

  • When do you feel the most like you?
  • Do you believe in destiny?
  • What does your perfect date look like?
  • What is your love language?
  • Where should we go this weekend?
  • I asked your fellow angels and they say you should go out with me

We don’t believe in love at first sight, but we definitely believe in first impressions. If you decide to go for romantic flirty texts, play it cool and be observational. The best “line” you open with will be relevant, witty, and timed perfectly.

Things to Keep in Mind Before Delivering Your Pick-Up Lines

Before you start sending those pickup lines in hopes to break the ice, take a moment to check if you’re ready to keep conversation going. Here are the main things to consider: reveal flirty interest in their passions, pick a working pick-up line, and give them some special attention indirectly.

Show Interest in Their Passions But Make It Flirty

When you are interested in someone and want them to show the same curiosity in you, it’s going to take much more than a couple of compliments to get to flirty texting. If you want them to never stop thinking about you, you should take a moment to listen as they speak and see if you have the same interests.

The examples of things that can work are numerous: favorite TV shows or movies, common interest in books and video games, certain hobbies. Allow them to talk and ask questions about their interests. You can throw in some deep flirty conversation starters to encourage them to continue talking.

Choose a Decent Pick-Up Line

If you simply want to get a reaction from someone, then yes, you can pick any flirty conversation starter. However, if you want to nab that first date with that person you like, you need much more than a couple of flirty pick-up lines. Think of interesting conversation topics to follow up with as you get to know them better.

The best approach in a pinch is sincerity. If you have trouble coming up with flirty questions or a clever remark, don’t panic. Just say something nice!

Related reading: How to Keep a Conversation Going with a Girl

Fun and flirtatious is great, but keep it PG rated: don’t comment on a person’s body or be overly sexual. For example, “That shirt is an amazing color!” is sweet and will make the other person feel good about themselves. Meanwhile, “You have a hot body” is no way to start a conversation, as women may found it sounding offensive.

Give Them Some Special Attention Indirectly

Many people get uncomfortable with direct attention, especially when they can sense there is more of a reason than friendship for that attention. To improve the situation, give them some special attention in an indirect way.

You can secretly pay for their food if you see them at a restaurant. A good way is to send them a music video of a romantic song and tell that you thought they would like it. The bottom line: you don’t need to be in their face about it to make them feel good about being around you.

Conversation starter advice for those using the phone

3 Ways to Flirt Over the Phone

Virtually everybody has a phone. So, it’s no surprise that texting has become a key way to engage with someone you like. If you can’t resist messaging them, you may as well have fun and use this powerful weapon to your advantage.


You may or may not have made the first move, but it doesn’t matter. You have their phone number. Now, it’s time to put on that main character energy and start texting. This is your opportunity to deepen the relationship. You’ve gone beyond breaking the ice.

It’s easier than you think. Just pick up your smartphone and call them. Tell your guy you just wanted to say hey. Ask your girl how her day was. Next thing you know, you’re talking all night long. The next day, they’re going to smile every time they think of you. All you need is just to make that first step!

How to create pretty good chemistry while texting:

  1. Start by asking them about the best date they ever had or imagined. Your crush will appreciate that you’re asking about their desires. Even better, you won’t have to guess where to take them on your first date. You’ll know exactly what they want.
  2. Remember that talking via text can be a little difficult. Your emotions may not come across the way you think they are. Let your crush know where your head is by using plenty of emojis. You can also use the voice option or share the occasional picture.
  3. Once you’ve had some time to flirt and get to know your new guy or gal, you may try playing hard to get. Leave them waiting to hear from you – and if you do it right, they may start missing and dreaming about a relationship with you. But if you’re not sure, don’t let them wait for too long! They might pull back and find someone more attentive to date.

All in all, there’s nothing wrong with texting. It’s a great way to have a conversation or share that new picture you took last night. However, there’s just something special about talking on the phone with someone who makes you smile. Those deep conversations about your dreams, goals, and experiences are such an important part of building a dating relationship.

Use memes as flirty texts

Use Flirty Memes to Get Their Attention Without Being Awkward

There are times when flirty texts are a bit too forward and will lead to things being awkward between you and the person you like. If you want to get that person’s attention, try sending them memes with a bit of a flirty theme. This can lead them to think that you have a great sense of humor and your jokes will allow you to ease into more serious flirting.

The best time to do this is after you’ve gotten to know their sense of humor a bit. Then, you can decide whether that cocktail o’clock meme your grandma sent you is going to be appreciated or not.

Dating Apps

The good thing about dating apps is that you don’t have to wait to see who makes the first move. Instead, you just create a great profile, add some pictures, and then wait for a guy to notice you. While that’s happening, you can also spend your time viewing profiles and flirting with the potential dates you like.

What does this have to do with flirty conversation starters? To start, your profile is a great place to insert some clever one-liners and other remarks to get people to talk with you. Also, does your dating app help you with icebreakers when you want to say hey to someone else? If it doesn’t, maybe you need to download something new!

Types of Flirty Lines to Avoid and Why You Should Avoid Them

When it comes to having a flirty conversation with someone there are some flirty texts and phrases that most of the time will simply lead you to be ghosted. Flirty text openers are supposed to allow you to get close to the person you like through small talk. However, there are starters and types of starters that will lead you high and dry when it comes to the world of romance.

Related reading: How to Ask a Guy Out Even When You’re Totally Awkward

1. Comparing Them to Others

Telling someone they look like somebody who is attractive can be a great compliment. However, it can become disturbing if you only like them because they look like your childhood celebrity crush and you can’t stop comparing them to that crush. After all, do you like them or do you just like their face?

2. Anything Having to Do with Сhildren

Starting a family is a big reason many people start to date. However, phrases like “Hey baby, are you an orphanage because I’d love to give you some kids” are cringe. Opening up a conversation with someone you like this way will leave you with nothing but binge-watching their Insta stories all night long. Just consider a more elegant approach if you’re interested in the subject.

3. Just Sending Them a Picture

If you want a relationship, sending your pic over a phone is not enough to establish something meaningful. Landing yourself a girlfriend or boyfriend of your dreams requires extra effort. So, if you are interested in someone, show that and make yourself interesting to them!

Related reading: A Guide on How to Be a Better Boyfriend

Bottom Line: Have Fun!

Dating and flirting are meant to be enjoyable for both you. So, stop stressing over it. Relax, have a good time, and keep things light. You’ll find a way to make a sincere connection before you know it!

Dating Tips Author
Shelly Standford
After a devastating relationship breakup, I threw myself into the dating scene by registering on Hily. I had over 100 dates - some absolute disasters, some pretty average, and some that were actually great. So many stories to tell and insights to share with you guys!

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