Flirty conversation starters

6 foolproof ways to break the ice

You see a cute guy and wondering what to say? How do you make that first initial contact and on top of that create a bit of chemistry? These flirty conversation starters are the answer to your questions.  

Or you got a number from a cute guy and wondering what to text him. These ideas work both in the real world and over text. Make sure you check out my article How to text your crush without being boring, for more ideas.

What you say is not important

The important thing is that you say something because when you initiate a conversation with a cute guy what you really are saying is; It is ok to talk to me. I’m interested in talking to you.

Oftentimes we spend too much time thinking about a great opening line. The truth is that your first line doesn’t need to be perfect, you just need to start a small conversation.

If your effort falls short  

Flirty conversation starters are all about being brave. Your effort might not be rewarded. The guy might not be open for a conversation.

Be ok with this outcome and your attempt at flirting will have the needed confidence.

There could be a thousand different explanations as to why the guy doesn’t pick up the conversation. He might just be shy or startled by your forwardness. Don’t make it about you, instead, be proud that you tried to make a connection.

1. Make a comment about something

The first flirty conversation starter is the easiest one, and it is you not being flirty at all.

The truth is that starting a conversation in itself can be a bit flirty, so you really don’t need to say anything flirty. The mere fact that you instigate is already a big step forward.

This holds true for texting as well.

State something fairly obvious

If you want to start a conversation with a stranger the easiest way is to make a comment about something very simple. For example “It’s so cold today.” “The train is late.” “I can’t believe how popular this place is. It’s only 4 o’clock.”

Remember, what you are really saying is; It is Ok for you to talk to me.

When he answers you can follow up with something more personal, for example, “How is your drink?” or “How is your day going?” or “Are you here with friends?”

2. Make a funny comment

If you want to add a bit more personality to the flirty conversation starters above, you simply put a more personal spin on your statement above.

I hate the cold, but I love watching the snow.

The trains seem to be late. Luckily I brought a good book.

Don’t worry, I’m not going to kill anyone to get served a drink.

The comment can be very short, but do inject a bit of humor. Trying to be funny to a stranger is already a bit flirty. It’s also a good way to start a fun conversation.

3. Give him a compliment

If you want to bring a bit more flirting to the conversations, the best way to do that is by giving him a compliment. For example;

I really like your sneakers.

That’s a cool watch. Let me take a closer look.

Your jacket is super nice. Where did you get it?

When a guy wears something, he has carefully picked it out. So saying that you appreciate his taste is a good start.

Comment on his behavior

You can also compliment something he is doing, for example;

You seem to be well-prepared.

I like how patient you are.

You seem like a guy who knows what he is doing.

The more you can tailor your comment to the exact situation, the more genuine you will come across.

If you want to add more sensuality to your interactions, check out How to turn a guy on over text. If you are brave you can use some of the lines IRL.

4. Ask for advice

This is another great flirty conversation starter. We could all need a bit of advice from time to time. Men love to give advice, it makes them feel like a hero.

You can start by asking “Can I ask you something?” Thus, you get his consent to the two of you having a conversation. From here it’s easy to follow up with a question.

Which cupcake do you think is the best at this coffee shop?

Are you from here?

What is a good restaurant around here?

What is a good bar around here?

Do you have a favorite spot in this area?

Is there something I shouldn’t miss when I’m here?

Ask him about his plans

If he is not from there you can ask him why he is visiting. You can still ask if he found a favorite place. Ask what kind of activities he is planning to do?

By asking this sort of question you find out a lot about who he is.

If he says, “We are here to celebrate my friend’s birthday.”

You can say “So you are here with your girlfriend?”

Ask about his status

Every time a guy uses “we” in a sentence, you can ask about who he means. Do it casually so as not to come across as a creep.

Asking a guy questions aimed to try and find out if he is single is indeed very flirty. But if he is single and you do it in a cute way you will be very memorable, since most girls are not that forward.

Even if he doesn’t follow up by asking for your number, you can still be proud of yourself, by trying to find out his status you gave him a compliment. It’s nothing wrong with letting guys know when you find them attractive.

5. Ask for his opinion on something

People love to give you their opinion on things. Most men have a lot of opinions about everything.

Asking a stranger for his opinion is in itself flirty because it means you value his opinion without even knowing him.

For example;

How did you think that team played in that game? (Insert a team and a game you know something about.)

Any form of sports questions is great, especially if you meet the guy in a sports bar. Otherwise, tailor the opinion you ask for to the situation you find him in.

For example, if you see him on your commute, you can ask him about his opinion about commuting.

Ask a music-related question

What do you think of the latest Taylor Swift album?

Music questions are also a good flirty conversation starter if you are out and about.

What was the last concert you attended?

So do you like to go out and watch live music?

How often do you come here?

Ask a political question

If you are brave you can ask about a political issue that’s being debated. Ask him about his opinion on global warming. Or his opinion about cryptocurrency.

Some people believe that you shouldn’t bring up politics in dating situations and that politics is not flirty. I believe the opposite; a good political discussion is hot.

If your political views don’t align, better to find out now than later.

If you are in a bar and it’s a bit late, you can ask if he believes men and women can just be friends.

The good thing about picking a sensitive subject is that you are bound to get into a heated discussion. You can easily involve more people and the whole thing will be interesting. If nothing else, you will learn something new.

6. Make fun of him

Yes, this tactic can absolutely backfire. The guy might find you annoying. But if you succeed, teasing a guy is a great way to create chemistry.

It’s also one of the best flirty conversation starters. The best way to tease him is in a way that also gives him a compliment.

I can tell that you spend too much time at the gym.

Your taste in music is not the best.

So you ordered the burger, like a typical guy.

Read my article How to tease your crush, to learn more about this very important aspect of flirty interactions.

Be fun and creative

This kind of funny remark must be expertly tailored to the situation where you spot him. Many times, they will fall short. But if you practice you will master this flirty art form.

Keep it neutral

You also don’t have to add your opinion to your comment, you can simply observe him and tell him what you see. Most people like it when another person sees them, even if that person is a complete stranger. There is something flattering about being observed.

Teasing works if you already know the guy

A flirty conversation starter that makes fun of the guy in question is a good move if you already know the guy a little bit. Then you will have enough information to tease him without being rude.

I knew you were going to order that.

I knew I would find you here. You never miss a happy hour, do you?

Make him defend himself

It’s called negging in the pickup community. (It has a bit of a bad reputation, but if it’s done right it is actually fun.)

Although it will not work on guys with low self-esteem, confident guys will love it. When you make fun of a guy and put him in a stereotype, you elicit an emotional reaction in him.

Also, most people love a good debate, and most people can laugh at themselves.

Do share something you have observed about him and don’t go easy on him.

A Finale Note

Flirty conversation starters are about making life fun. It is about taking risks and not letting all those cute guys slip away.

Be brave, and take the initiative to start a conversation.

When you have done this a couple of times you will realize that initiating is not as difficult as you thought. You will be able to come up with your own flirty conversation starters.