How to Flirt on a Date if You’re a Shy Guy

Are you the type of guy who wants to be in a relationship, but has no clue how to win the heart of your date?

You might be wondering to yourself, “Where have I gone wrong? I’ve learned how to make conversations, how to read body language—why does it feel like she’s still not into me?”

Yes, you’ve learned how to make date night go smoothly, but there’s one problem—where’s the pizzazz? It wouldn’t be a date without a little tease and playfulness, right?

According to Cosmopolitan, flirting with your date is a non-negotiable in the dating world. That means if you want to let someone know you’re into them, then you'd better show it.

Men, grab a paper and a pen, because it’s time for you to learn how to flirt on a date.

Confidence is Your Best Perfume

How many times have you seen beautiful women being attracted to a not-so-visually appealing guy, and wondered, “How did he do that?”

Confidence!

Confidence attracts women, and women can vouch for it. While they may not initially be attracted to you, by being confident with what you do and say, you’re bound to receive a little seductive look from your lady friend.

Understandably, not everyone is confident in talking to a woman, but they need to understand that opportunities, such as dating, require some effort in handling uncomfortable situations.

Be A Little Suggestive

Women love to fantasize. They love thinking of doing romantic things with their potential boyfriend, or even the idea of being intimate.

Which is why you should be a little suggestive and play with their fantasies.

However, this doesn’t mean you should outright tell them to come to bed with you—NO! Be subtle, play around with the thought of going out on a beach date, or going on a motorcycle ride to the mountains—fill their minds with possibilities.

Flirty Questions to Ask a Girl

If you want to know how to charm a girl, you have to ask some spicy and intimate questions. Make the date playful and light-hearted; it’s date night, and being bored is the last thing both of you would want to be.

Since it’s going to be your first date, here are some non-intense flirty questions to ask a girl to make your date interesting:

What song describes the way you love someone?
Are you a front hugger or a back hugger?
Do you prefer cocktails and drinks, or a cuddled-up movie date night?
If love at first sight isn’t true, why does my heart race every time I look at you?
How many times have you caught me staring at your pretty face?

Don’t be afraid to ask these or similar questions—spice up your date night!

Survey the Connection, Make Slight Touches

They say that accidental brush-ups or touches are a turn-on because it signals “maybe we can venture a little further from our safezone.”

Check your connection with each other. Ask her if she feels comfortable enough to hold her hand or sit closely beside each other.

Remember, genuine consent is essential for making your date feel safe. If she is comfortable with you holding her or being close, honor that. Conversely, if she says no, it is crucial to respect her decision.

Let’s assume she does allow you to be closer to each other. When you’re with her, don’t force yourself to hold her or brush up against her shoulders; when the moment calls for it, go for it.

Don’t limit yourself to emotional connection; physical connection is important too.

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You’ve finally got the gist of how to flirt on a date. Keep in mind that this is not a cheat sheet designed to help you win your date's heart; instead, think of it as a guideline. While it doesn't guarantee a follow-up date, it provides a foundation for understanding how to create a spark in your connection.

Frequently Asked Questions

What is the most important thing for a shy guy to flirt successfully?

Confidence is key. Though challenging for shy individuals, projecting confidence in your words and actions is highly attractive and can elicit a positive, seductive response from your date.

How can I flirt subtly without being overly sexual?

Be suggestive by playing with romantic fantasies, such as suggesting future dates like a beach trip or a scenic ride. This creates possibilities without being overtly demanding.

What are examples of playful questions to ask on a first date?

Flirty, light-hearted questions include "Are you a front hugger or a back hugger?" or "Do you prefer cocktails or a cuddled-up movie date?" These make the conversation fun, while at the same time being less intrusive.

Is physical contact necessary for flirting on a date?

Yes, physical connection is important alongside emotional connection. Slight, consensual touches or holding hands when the moment is right can signal a willingness to explore a deeper relationship.

Should I try to be someone I'm not to appear more confident?

No, aim for genuine confidence. Trying to be someone else is unsustainable and can undermine the trust and connection you are trying to build.

What should I do if my date says no to physical closeness?

You must respect her decision and immediately stop any attempts at physical contact. Genuine consent is essential for your date to feel safe and comfortable.

References:

Wallace, Megan, and Sophie Williams. 2024. “How to flirt like a pro, according to the experts.” Cosmopolitan. https://www.cosmopolitan.com/uk/love-sex/relationships/a36329/how-to-flirt/.