9 Flirty Questions to Ask a Guy That Make Him Obsess Over You

One of the most important steps in building a romantic relationship is the part where you turn this new “friend” into someone that you can flirt with and someone you can date.

Some people have a way of instantly doing this, perhaps by their good looks, strong eye contact or their tendency to be bold and say whatever they’re thinking. But for others (probably most of the population), starting sexual tension can be a challenge.

Maybe it feels awkward. Or maybe you sense reluctance on his part to flirt with you. You’re confused…does the guy like you or not? If the guy isn’t blatantly hitting on you, and you don’t want to ask him out directly, then what you might try is asking him flirty questions.

Flirty questions can put the thought of sex and romance into his head without making things too awkward. This is a good way to give him a signal showing that you’re interested, IF he’s interested too.

Here are nine questions to try, with an explanation on why they’re so effective.

1. “Who was your first kiss?”

This question allows him to travel back in time and confide in you about a very intimate moment in his life. Good idea, because talking about intimacy does encourage him to confide in you and start a bond. It may even make him think back to feelings of innocence and wonder. These are all positive associations.

2. “What’s the strangest thing you’ve ever done? OR “What’s the strangest thing you believe?”

This question really allows him to open up his eccentric side, and in essence the “side” he hides from the world. We are trained by society to agree with the majority opinion. But deep down, we all have weird beliefs, weird hobbies or interests, and are just dying to tell someone else about them. You have to figure men even more so, since many of them believe they have to suppress feelings or unusual thoughts. Simply put, learn his “weirdness” because it’s close to his heart and may even be connected to his feelings of love.

3. “What was the happiest moment or day of your life?”

This question makes him take a trip down memory lane. He remembers a time when he felt perfectly content. And it’s safe to say he probably doesn’t feel that way now. We tend to idealize the past and especially early childhood experiences. The real value of the question though, is that you can deduce what really made him happy and what can still make him happy. Help him discover a forgotten need.

4. “What are you most thankful for in life?”

This question hits close to home—his values and the things he treasures most in life. It’s also a subtle way to remind him to focus on the positive things in life. Over time, he will begin to associate you with positive things. He will find this attitude magnetically attractive and not just because positivity is contagious. It’s quite likely that his own parents taught him to be grateful to others and appreciative of what he has. It’s a good quality he will begin to see in you.

5. “What’s your dream?”

Every guy has a dream. Especially those handsome, smart and funny guys. Ambitious men usually come across as very attractive, heroic and attentive. What better way to help him open up then asking about what he wants to do the most—what’s his lifelong dream? Whether it’s simple or complex, show enthusiasm for what he describes. As you get to know him, believe in him and his ability to accomplish this dream. This is what will ultimately help him fall in love with you.

6. “Can I get your advice on something?”

Deep down, every man wants to be a good provider and be respected for his ability to help, to solve, and to be of service. That’s why this is such a loaded question. Asking him to provide his intellect, wisdom or area of expertise is a major ego boost. The better a man feels about himself, the better he feels when he’s with you.

7. “What would your Marvel (or DC) universe superpower be?”

Chances are, he has an opinion on comic books, superheroes and all things action-oriented. But asking him this seemingly innocent question gives you some insight into his thinking. A man’s superpower is actually a symbol for how he sees himself and what good he wants to do for the world. But the real joy here is not you analyzing him—it’s the joy he gets from explaining to you what superpower he would choose. He’s going to think you’re an expert conversationalist since you can evoke feelings and thoughts out of him while keeping it fun.

8. “What do you tell your friends about me, anyway?”

This is a great question because it can easily follow up a casual conversation about his friends, but it’s also quite subversive. On one hand, you’re giving him the hint that he should introduce you to his friends (which implies more intimacy, more trust) while also gauging what he thinks about you. It’s also a great opportunity to let him impress you by describing your good qualities.

9. “What DO you like about me?”

Most guys are going to say something along the lines of “You’re beautiful” or “I like you” or “You’re good, attractive, etc.” without much thought. It’s a minimal risk, even for a shy guy who’s afraid to make a move.

So the next time he does this, call him out on it. Ask him what he likes about you and if you’re really daring, ask him what he likes about you physically—your best feature. It may embarrass him a little if he’s shy, but this will actually give him the confidence boost he needs to ask you out.

Remember that the objective here is to break out of that friend-zone by flirting with him and asking him questions that put him in the mood for romance and dating. It’s a challenge but it can be a fun one!

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Talk soon,

Matthew Coast

P.S. If you’ve been banging your head against the wall because you’ve fallen for a man who’s frustratingly unavailable…

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About The Author

Matthew Coast

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