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20 Questions to Ask Her to Show Your Sensitive Side

Not all women go for the caveman and a sensitive soul is highly attractive. To show her you’re not like the others, ask her a few of these questions.

sensitive questions

Deciding which role to fulfill is a real tough call for the modern guy in the dating arena. On the one hand, we’re told that all women love the alpha male, the bad boy, and the serial womanizer, yet when we act that way, we’re given a slap and told to shove off. On the other hand, magazines like to tell us that we have to be open to a softer, more considerate, more feminine approach, only to be told to “man up” and laughed off in disgrace.

Well, if you want to attract the woman who is right for you, then the answer is simple: BE TRUE TO YOURSELF. Acting a part is just going to deceive, in addition to mismatching you both.

20 soulful questions

The following list is intended for men who are naturally more sensitive, and will help them open up to the current object of their affections. These questions are designed to open and reveal the soul.

#1 What are the top five things on your bucket list? A great question not only to try and work out the inner self of your partner, but also a chance to maybe try and facilitate her dreams. After all, what could show your sensitive side better than that?

#2 What are you most afraid of? Fear is a powerful emotion, and by asking this question, you have the opportunity to sympathize and empathize with her, as well as help her through her fears.

#3 Are you an affectionate person? Asking this question shows that you are keen to respond to her needs. It also gives you a chance to show that you are a lover of affection—if that is, indeed, the case.

#4 If there’s anything you could have done differently, what would it be? Regret is one of the most negative emotions, and by asking her this, you may be airing something she didn’t really want to… but it gives you a chance to talk her through it and show what an emotionally supportive rock you are. Support is an attractive, unusual trait in a male.

#5 What’s your favorite…? Food, place to go on holiday, perfume… etc. It’s an off the cuff kind of question, but whereas most guys would forget the answer in a heartbeat, you’ll be storing it up to surprise her on her next birthday, or other gift-giving occasion. [Read: 20 funny questions to ask a girl and leave her ROFL]

#6 What’s your most special memory? This question shows that you embrace all of who she is, even her past before you met her, and that you want to share her precious moments. This shows true emotional strength and a real sensitive side.

#7 What’s your greatest passion? Listening is a skill that most men don’t have. By asking her about her passion, even the most tight-lipped lady is likely to speak at length, giving you the opportunity to show just how strong your listening skills are.

#8 What advice would you give your younger self? This question gives you rare insight into her personality, as well as showing your ability to assess and discuss deeply emotional subjects.

#9 What would you do if you won the lottery? Her answer is important, or course, but so is your response—especially if you’re the sort who would contribute it all to charity, rather than buy a tropical island! [Read: 50 relationship questions to test your compatibility instantly]

#10 If I ever did anything to hurt you, you would tell me, wouldn’t you? Women do not expect this level of sensitivity and emotional openness from a guy and they’ll find it hugely refreshing.

#11 What are you most proud of? Similar to number 7, this gives her a chance to express herself, and for someone else to take notice… a winner in the sensitivity stakes.

#12 Do you need some space? For the more in-depth and, perhaps, intense relationship, expressing this level of understanding and flexibility is likely to make you a saint in her eyes. And it could well save the whole thing.

#13 Where do you see yourself in 5 years? This shows a true willingness to listen to and empathize with her aims and ambitions, but also subtly hints at the fact that you want to be part of her future. She’s bound to love that.

#14 Would you tell me if you were ever attracted to someone else? Again, emotional honesty is a rare trait in a guy, and expressing this honesty without ire or accusation shows true strength of character and a very real sensitive side.

#15 If you could change one thing about yourself, what would it be? Find this out and then tell her, in so many ways, why you couldn’t possibly agree with her. [Read: How to charm a girl and flatter her into liking you]

#16 Can you tell me if I’m doing it how you like it? We’re getting a bit physical now, but sex is an important part of a relationship. Showing that you are sensitive to her needs is highly likely to increase your appeal.

#17 What did you want to do when you were a kid? You want to know everything about her—past, present, and future. That’s what this question tells her: her every moment matters to you.

#18 How many people have you ever truly loved? Discussing love can be very difficult—even for some women. For a guy to come out with this question, and to honestly reply with his own answer, shows a sensitive side that few can boast of.

#19 Do you want to try something new? Whether you’re talking about the places you eat, the usual places you go on holiday, or sexual positions, this question shows that you are responsive and sensitive to her needs.

#20 If you could change anything about me, what would it be? What could better expose your sensitive side than an obvious willingness to change in order to remain in the life of the one you love?

[Read: 50 really cute things to say to your girl that’ll make her love you more]

If you have a sensitive side that you want to expose to the woman of your dreams, then do so. By hiding it, you’ll only be hurting yourself—and you certainly won’t end up with the woman who’s right for you.

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David Cullen
David Cullen
David Cullen is frequently described as erudite, insightful and witty – but only by himself and only after several large glasses of Rioja....