10 Good Conversation Starters for Introverted Men

How to start a conversation with an attractive woman

Imagine you’re simply going about your day, stopping in for a coffee near work, when a woman catches your eye.

You notice that she holds the door for an elderly couple and then smiles kindly at the barista before ordering her drink. From what you can see, her style and overall vibe are exactly what you’re looking for.

She’s done ordering and is now waiting patiently for her drink to be made.

What do you do?

Do you stay put as the moment slips by, deliberating whether to say something,maybe trying a pick up line and then worrying you may say the wrong thing?


Do you gather courage, walk over ready to break the ice, and strike up a conversation?

Today’s post is all about helping you overcome that moment of hesitation so that you can make the most of a special opportunity!

That’s why we’ll be sharing 10 good conversation starters specifically for introverted men!


Why is it important to have good conversation starters in your back pocket?

When you know what you’d say if you walked up to that woman, it makes it a whole lot easier to strike up a casual chat!

However, you first need to develop authentic, steadfast confidence.

The reason being, true confidence is THE number one variable that can turn what could have felt like a forced, awkward conversation into one that’s filled with joy, curiosity, and chemistry.

That’s exactly what this free 22-page ebook helps you with: building your confidence so that you can have an enjoyable conversation with anyone!

Download it here.

Now, let’s dive in!


The 10 best ways to start an awesome conversation

When it comes to starting conversations… context is everything.

Some of these good conversation starters only work effectively in certain settings. That’s why we recommend you save this post (screenshot, bookmark, or send a link to yourself) so you can keep referencing it whenever you need to!

1. “Your ___________ is impeccable. Have you ever ___________?”

There are so many ways you can adapt this one to your exact situation! Here are some examples:

  • “You are so great with kids. Have you ever been a nanny or a teacher?”,
  • “Your hairstyle looks amazing. Have you ever considered doing hair professionally?”,
  • “You sound so knowledgeable about coffee. Have you ever been a barista?”,
  • Or “Your running form is impeccable. Have you ever run in any races?”

By starting with a compliment and ending with a specific question, you’ll make her feel important and interesting (after all, people love to feel noticed)… which ultimately helps her feel much more excited to talk to you!

2. “You seem so ___________! What keeps you that way?”

If you notice something that appears to be true at the moment though it may not always be the case, this is a great, non-assuming way to start small talk. Check out these variations:

  • “You seem so present and focused! What keeps you that way?”,
  • “You seem very fit and strong. What keeps you that way?”,
  • Or “You seem like you’re up-to-date on world affairs. What keeps you that way?”

We also love this conversation starter because it ends with an open-ended question, which gives her the opportunity to take the exchange wherever she wants to; there’s no wrong answer!

3. “You are a very beautiful person. I especially noticed ___________.”

This is a good conversation starter if you’re feeling a bit bold! You can fill in the blank with something related to her appearance, something she did, or the way she carries herself.

The nice thing about this one is that many women appreciate a man who can be direct and confident while making his intentions very clear.

4. “These ___________ are so good. Have you had one?”

If you’d prefer a more discreet approach, this is a great option. In fact, this is such a good conversation starter that it works universally for starting a chat with anyone, whether you’re interested in them romantically or not!

  • “These nutella crepes are delicious. Have you had one?”
  • “This cycling class is such great exercise. Do you work out here often?”

5. Lean on this handy acronym to guide you: F.O.R.D.

This widely-shared method (original source unknown) can be a wonderful framework to follow, especially during a first date.

If you’re concerned about running out of things to talk about, this four-in-one conversation starter can help you keep good momentum and energy as you chat:

  • F: Family (you can ask about proximity, number of siblings, emotional closeness, and who she’s most similar to)
  • O: Occupation (feel free to inquire about her type of work, schedule, interest level, and career goals
  • R: Recreation (when you’re curious about what she does for fun, this topic can branch in so many fun directions!)
  • D: Dreams (you can learn so much about her by asking about her future hopes and goals!)

These are good conversation starters for introverted men who want to keep talking without wondering about where to steer the chat next!

Now you might be wondering what will be left to talk about on your first date if you cover all of these topics in your first conversation before your date. Happily there are so many more light and fun topics you can venture into, including each of your favorite holiday, favorite restaurant, favorite movies, favorite foods, favorite subjects, favorite season of the year, as well as any tv shows she’s watched recently, pet peeves…the list goes on and on!

Or you can try a specific question like “If you could travel anywhere in the world, where would you go first?” Check out our article on Conversation Topics and Tips for more great ideas!

6. “You look like you know what you’re doing, ___________. Do you have any suggestions for me?”

We love this one because it compliments her ease and confidence while illustrating that you see a strong woman with admiration, not intimidation.

Here are a couple of ways you can make this good conversation starter work for you:

  • “You look like you know what you’re doing, choosing that merlot. Do you have any suggestions for what I could pair with the steak I just picked out?”
  • “You seem to be familiar with this bookstore. Do you have any advice for a first-timer?”
  • “You are navigating these office dynamics with such discernment. Any advice for the new guy?”

The nice thing about this one is that it encourages a longer conversation beyond a one-word answer.

7. Simply comment on your shared environment.

This can take on many forms, from acknowledging how long a line is, how cute someone’s baby is, how fun the decor is, or how lovely the day is.

It’s one of the easiest conversation starters on this list because you only have to voice something you notice. Many people do this all the time naturally, so it won’t come off as too direct if that’s not your style!

Our advice here is to keep your comment positive. If she’s having a bad day, it will help bring her spirits up, and if she’s feeling superb, it will help make her feel even better!

This can work really well with an extroverted woman who is willing to chime in, agree or disagree with you, or casually acknowledge your comment.

Keep in mind that introverted women may be less likely to respond vocally, so if you notice that she gives you a smile or a knowing nod, it’s a good idea to draw her in by adding a “Don’t you think?” to the end of your comment!

8. “How about these ___________, huh?!”

This is another wonderful, non-threatening way to provide anon-ramp to starting a conversation. For example, you can use this framework by saying…

  • “How about these great gas prices, huh?!”,
  • “How about these Halloween decorations, huh?!”,
  • Or “How about these crowded subways, huh?!”

Watch her body language and facial expressions for cues that indicate interest and encouragement versus discomfort or ambivalence.

That way, you can decide confidently whether to ask a follow-up question or let it drop.

9. “Hey, I just had to say, I really liked ___________.”

This is a really special way to encourage something wonderful about a woman that may have otherwise gone unnoticed.

Here are a few variations:

  • “Hey, I just had to say, I really liked the way you stood up for that person with special needs.”,
  • “Hey, I just had to say, I really appreciated how you deescalated the tension in here.”,
  • Or “Hey, I just had to say, I really liked how you waited a few extra moments to let that family through the door before you.”

This is a good conversation starter that shows your interest and desire to get to know her while telling her why you’re interested. Women find this very flattering, and it often makes them feel more open to further communication!

It’s also a great way to come on slow instead of strong. After all, this is a script you could use to acknowledge the best in your friends and family members as well as your romantic interests!

10. “I noticed you, and I had to come say ‘hi.’”

If you are looking for one great conversation starter that you can use anywhere, this 10-word sentence can work in ANY context!

You don’t have to add anything else in if you don’t want to. By leaving this comment hanging in the air, you give the woman you’re talking to a great opportunity to react authentically.

If she isn’t interested, she can respond with a one-word answer or she can choose to have no response at all. While this isn’t the ideal outcome you’d be looking for, you can feel at ease knowing right from the start that there isn’t a connection.

On the other hand, if she reciprocates or says she’s glad you came to say, that’s a clear green light for you! You can find out more about this beloved 10-word phrase of ours here.


Closing thoughts on good conversation starters

Woman And Man Talking At Pier - Good Conversation StartersThe practical, adaptable scripts you’ve discovered today will help you connect well with women and enjoy doing it, all while staying true to yourself!

Today, we covered 10 effective ways to kickstart a conversation.

So now what?

  1. Take a look at this related article, Conversation Topics + Tips: Guide For Introverted Men.
  2. To make sure your conversation starters feel natural and authentic, download our free ebook, “Why PUA Doesn’t Work for Introverts & What Works Instead.”
  3. For more personalized support, check out our program, Become a Benevolent Badass!

This in-depth, 1:1 coaching program will put you on a self-development fast-track while showing you the best way to…

  • Find your personal true north,
  • Bring out your best around others, and
  • Become an intentional social leader.

To feel confident while connecting with anyone in any social setting, Become a Benevolent Badass today!

Picture of Micayla from IA
Micayla from IA
Micayla is resident writer here at Introverted Alpha, which is known as the premier dating coaching company for introverted men; featured by Forbes, Business Insider, Cosmo, and more. Pick up your free copy of our 22-page ebook inside the blue box just below.

Attracting An Amazing Girlfriend Starts with Finding Your Own Vibe.

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In this powerful free 22-page ebook, “Why PUA Doesn’t Work for Introverts And What Works Instead,” you will uncover… 

–> 3-step exercise to find what makes you uniquely attractive

–> Why the “pickup artist” approach will never work for introverts and what works instead

–> How to attract women naturally being your best self

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Attracting An Amazing Girlfriend Starts With Finding Your Own Vibe.

In this powerful free 22-page ebook, "Why PUA Doesn't Work for Introverts And What Works Instead," you will uncover...


--> A 3-step exercise to find what makes you uniquely attractive
--> Why the “pickup artist” approach will never work for introverts and what works instead

--> How to attract women naturally being your best self

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