The Art of Flirting: 7 Questions to Ask Your Crush That Will Let Him Know You're Interested

The Art of Flirting: 7 Questions to Ask Your Crush That Will Let Him Know You’re Interested

Posted by in Black Love Advice

We’ve all had a crush… We’ve also all had a crush that failed to pick up on the signals we were trying to send them.

Were you not obvious enough? Are you flirting the wrong way?

What if I told you that all it takes to let him know that you’re interested is to ask him a few questions?

Yes, it’s true.

He may not have picked up on your flirtatious signals yet, but if you ask him these questions, he will undoubtedly realize that you want to be more than friends, co-workers, or acquaintances.

Let’s get started.

Here are 7 questions to ask your crush that will let him know that you’re interested…

1. “So…have you been working out lately?”

The Art of Flirting: 7 Questions to Ask Your Crush That Will Let Him Know You're Interested

What can be a better way to get your crush to notice you than by letting him know that you notice him?

As corny as that line may sound, asking your crush if he works out provides a subtle indication that you have been checking him out in more than a professional or friendly manner.

Add a smile, a gentle touch to his biceps, and direct eye contact, and he will be hooked in.

We all love compliments, and this compliment can lead to a first date…

2. “What do you look for in a woman?”

Okay, this may feel like it’s a little too far away from your comfort zone, especially if you twos conversation has never journeyed in this direction.

But trust me… It gets results…

Asking about the qualities your crush would look for in a partner is a great way to find out if you two will make a good match.

Although it isn’t overtly flirty, this is one of the primary questions to ask your crush for one reason: You can objectively inspect your level of compatibility.

From this question, the conversation can now be directed to things about love, dating, relationships, and other topics that will give you both ample opportunity to reveal your level of interest in each other.

3. “How do you still not have a girlfriend?”

Interest, desire, and flirtation. Those are the three things you are likely to convey if you ask a person this question.

And if you think about it, what better way to let your crush know that you’re interested in being more than friends than letting them know that they’re too good to be single?

Men love this type of validation.

Don’t be shocked if he responds with something along the lines of “I don’t know. Maybe we should go on a date?”

4. “What’s your idea of a perfect date?”

Even Stevie Wonder could see that you’re flirting if you ask a man this question.

As you continue to make it clear that you’re digging him, discussing dates and relationships more frequently will increase the level of understanding between you two (if he hasn’t asked you on a date already.)

Not only will you get to know how your crush imagines a perfect date playing out, but you can also surprise him later with an invitation that matches those expectations.

By gently guiding your conversations towards romantic topics like date ideas he will definitely understand that you want to be more than friends…

5. “Can you help me with (fill in the blank.)”

One of the keys to letting a man know that you are interested in him and value his presence is by letting him know that he’s needed.

You can ask him to help you with things like a problem with your car or an assignment at work.

This also gives you the opportunity to spend more time together, which is definitely an added plus.

Men tend to show their interest and affection by their actions.

If he seems to always be ready and willing when you need a helping hand, he’s likely as interested in you as you are in him.

For more signs that he likely has a mutual interest in dating you, check out “Is He Flirting With Me? Here Are 12 Signs That He Definitely Is!

6. “What’s the most romantic date you’ve ever been on?”

Again, this is a question to ask your crush that you can’t go wrong with.

By asking about their most romantic date, you’ll not only be indicating that you’re interested in learning about their personal life but will also get a clue about their likes and dislikes in a date scenario.

You can also slide in how “that sounds fun… We should do it sometime.”

Without a doubt, they will understand exactly what you’re saying…

7. “Who do you think should make the first move – the man or the woman?”

The Art of Flirting: 7 Questions to Ask Your Crush That Will Let Him Know You're Interested

Since most of the questions on this list are rhetorical, you don’t have to be nervous or self-conscious about what answer might come out because you already know the likely responses.

Asking the person you’re interested in about who should make the first move is not really about finding out if you should make a move first, but rather how they think dating and relationships should work.

In the end, being that the question is of a romantic nature, they will understand that you are hinting at an interest in them, especially when couples with a few of the other questions on this list…

And subtly letting a person know that you’re interested is the primary goal of flirting in the first place.

Objective achieved.


So I have a quick story ladies.

Last night while talking to my boyfriend about this article he made a suggestion in the middle of me writing…

“This goes against the norm,” he said, “and it’s definitely not for everyone… But what if women just cut the flirting short and let men know that they’re interested?”

We debated this back and forth with him holding the opinion that nothing displays more confidence than being direct and making your intentions loud and clear.

I agree to an extent.

But I strongly believe that a man should always be the one to ask a woman out.

If he doesn’t have the courage to ask you on a date in the face of all of your flirting then how much of a man is he really?

While nothing cuts to the chase like the direct approach of asking a crush out, the 9 questions to ask your crush mentioned above should serve useful for a woman that prefers a more traditional and subtle approach.

I leave off with this: Flirting is an art…and these questions will make the picture you’re trying to paint as clear as day.

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