How to Ask a Woman on a Date: 11 Scenarios and What to Say

Tips for introverted guys who want to ask a woman on a date

If you’re like many introverted men wondering how to ask a woman on a date, you may feel…

  • Worried about getting rejected,
  • Ready to ask, yet unsure of exactly what to say,
  • Confused as to how you get to that point in the conversation, or 
  • Overwhelmed by the whole experience, start to finish.

The truth is that you are totally not alone in feeling that way!

Keep reading to feel prepared, informed, and confident as you ask a woman on a date. Today we’re going to share 11 scenarios and what to say as you discover how to move a conversation toward a date with ease


Do you need confidence to ask women on dates?

When considering how to ask a woman on a date, half of the equation is building up the courage to do so.

If you have to “pump yourself up” or fall back on a cheesy pick up line to ask a woman out, these are signs that your confidence might not be at a healthy enough level to be asking women on dates quite yet.

The good news is that when you build your confidence on an unshakeable foundation, you won’t have to worry about what her response will be!

You can take a “yes” with humble pride, and you can accept a “no” with peace and gratitude.

In other words, your confidence is at a stable place when asking a woman on a date (or not) is something that is completely separate from your identity as a man.

So, how do you start building a sense of confidence like what we described above?

That’s exactly what this free 22-page ebook helps you with!

Download “Why PUA Doesn’t Work For Introverts & What Works Instead” now so you can circle back after you read this post!

Now, let’s dive in!


12 Scenarios and What to Say 

1. Start an enjoyable conversation

If you’re thinking, “That’s easier said than done!” then keep reading!

An enjoyable conversation is one that intrigues her, appeals to you, and makes you both want to keep talking to each other.

You can accomplish that by staying curious about her interests and adding energy to the conversation.

Check out this article for more tips on what to say!


2. Use eye contact to your benefit

Did you know that compelling scientific evidence suggests that eye contact can have a powerful effect on a romantic relationship?

Look into the 6 ways eye contact can shape your interaction and what you need to know about the duration, frequency, and context of eye contact so that you feel comfortable using this technique the next time you interact with a woman you’re attracted to.


3. Take action to make her feel comfortable and valued

Does she look cold? Offer her your jacket.

Is she thinking about ordering a drink? Pick up her tab.

Does she seem uncomfortable in the restaurant you both just walked into? Ask if she’d like to check out a place you saw down the street.

Whether you feel a little chilly, spend $5 on a drink, or create a whole new plan on the fly, a minor inconvenience or change of plan  can be a really big deal to her.

These subtle actions show you’re paying attention to her, which tells her that you think she’s worth paying attention to!

Moving from an acquaintance to a crush to a boyfriend can be a seamless process when you take the time to build trust and you’re willing to go out of your way to make her feel special.


4. Offer sincere compliments

We aren’t talking about general flattery here.

If you’re going to compliment a woman, be intentional! Choose something specific as you describe what you like about her, and only offer compliments that are completely genuine.

Read this article for 5 helpful tips on what to say to a woman you’re attracted to.


5. Keep your tone lighthearted and positive

When you’re too intense as you ask her on a date, she may feel a bit intimidated. On the other hand, if you’re too serious or uptight, she might wonder if the two of you will have a good time together.

A casual, playful, upbeat tone helps to either garner an enthusiastic “yes!” or the gentle yet clear alternative.


6. Behave confidently

As we mentioned above, confidence is the most important factor that sets you apart from other men AND helps you become the best possible version of yourself!

When you build that confidence internally with authenticity, you’ll gradually notice your newfound self-assuredness coming through in your social communication and behavior.

(If you haven’t already, here’s a reminder to download our free ebook on this topic to read after this post!)


7. Suggest a date that aligns with her interests

Does she love volleyball? Offer to take her to an upcoming D1 volleyball match. Did she recently get diagnosed with a gluten allergy? Find an accommodating restaurant in your city and see if she’s available to join you for dinner.

The point here is to invite her to do something that she can’t resist! By choosing an event or experience that’s already in her wheelhouse, you help her feel listened to, comfortable, and excited to share her interests with you.


8. Dress for success

While you don’t need to show up in a tux or comb your hair over, you’ll want to be mindful of the way you come off to others through your outward appearance!

When conversations move off of dating apps or from texting to in-person, you leave an impression on others by the way you dress, smell, style your hair, and move your body.

Even when you attend events where you’re not expecting to see someone you’re interested in, allow yourself to be prepared to be surprised! Taking pride in your appearance helps build confidence to interact with others at any time.


9. Remember to get her phone number

If you’re Googling “how to ask a woman on a date,” you may find yourself in a common scenario our clients and readers have shared with us:

You get so focused on asking her on a date that you forget to ask for her number so that you can work out the logistics later.


10. Avoid cheesy, overused pickup lines

When you’re aiming for a connection that can be created and maintained over time, an insincere pickup line is simply not the way to go!

(As a thoughtful, introverted man, you likely already knew that, though! We love how that’s not your speed anyway.)

If you’re searching for what works instead of pickup lines, that’s what our ebook is all about!

11. Let her experience your humor

When you make a few jokes, you show how dynamic your personality is and you let her in on what you think is funny!

On the spectrum of joke-telling, we have joke-suppressing on the far left and stand up comedy on the far right.

Neither of those extremes are right for you! Why?

When you hold back your humor or you force being funny beyond what feels natural to you, you withhold your most genuine self.

In contrast, when you let her in on your humor, you build the trust, intimacy, and joy she feels around you!

Remember: There’s nothing quite like sharing a laugh that can embolden you to ask a woman on a date!


Conclusion on how to ask a woman on a date

how to ask a woman on a dateNow that you know how to ask a woman on a date, you’ll be able to do so with confidence and emotional stability regardless of the result!.

Do you want to make sure your dating and leadership skills keep improving? We’re about to share the #1 action you can take to make that happen!


Your Next Step

First, start by downloading our free ebook, “Why PUA Doesn’t Work for Introverts & What Works Instead” to keep improving your dating and leadership skills beyond what you learned today.

Next, seek out the 1:1 support from dating coaches you can trust for advice on what works best when dating as an introverted man!

Consider our Launch Your Dating Life program to…

  • Be and feel sexually attractive,
  • Meet and connect with great women, and
  • Fill your dating funnel with quality dates.

Launch Your Dating Life is our 12-week high-touch, comprehensive program that will help you do all of the above, while feeling more like yourself than ever.

Launch your own dating life 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.

Introverted Alpha Ebook

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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