A lot of women think that asking how many women you have slept with and what your favorite sex position is what makes you more intimate with a man.

Trust me, it isn’t. It only shifts your intimate conversation to a sexual one or an awkward one.

Knowing each other’s number of sexual partners isn’t relevant to your relationship and it can only mess a good thing up.

Your number will always be too high and his too low in his mind. It’s better to avoid this topic altogether.

Feelings are more intimate in any case, that’s why asking deep questions and letting someone in no matter how afraid you are of getting hurt is where the bonding begins.

Of all the intimate questions you could ask a man, these are the most intimate ones:

1. Can I trust you?

couple sitting on the bench

Feelings are everything and most of us who have been wounded too many times fear that the worst will happen again.

This question is deep and if it’s answered with a hug and a promise that he is someone who can be trusted, you will feel safe and protected.

2. Have you ever cheated on any of your exes?

happy couple talking

If you are dating someone who has a history of cheating, it’s a huge red flag.

If he is someone who takes relationships lightly, it’s better to know right from the start.

3. What’s your biggest regret?

couple sitting on the floor outdoor

Or in other words, “What is that one thing that he wishes he could have done differently?” Don’t hesitate to share yours.

Not all dirty laundry has to surface all at once and you don’t have to share each and every regret you have.

This is just the start of getting to know each other better.

If a person has had alcohol or drug addiction or something along those lines, this is also a great way to make them admit that without being too forward.  

4. What is your most difficult challenge right now?

young couple sitting by the sea

If they are going through something difficult right now, this is a great question to make them open up about it.

Maybe they are stressing about work, going through some hard times, recovering from something, etc. and they don’t want to burden you.

This question gives them an opportunity to share whatever is on their mind and even if they don’t feel like they can share right away, they will appreciate your concern.

5. Be honest, what is the worst thing about being in a relationship?

couple sitting on the bench with their dog

Finding out what man doesn’t want is more important than what he wants.

If there are things about relationships in general that he doesn’t like, it’s better to know so you can avoid them.

6. Tell me something you are ashamed of and I will reciprocate?

romantic couple watching sunset

This is a cute question which can only bond you closer together. We all have things that make us blush in our cheeks and that we wish we hadn’t done.

This is a way of telling your partner that neither of you is perfect and that’s more than OK.

7. Name one thing you’ve never done before that you would want us to do together?

young couple in hug

This is a great way to kill two birds with one stone, so to speak.

On the one hand, you are showing that you want to know his wishes and on the other, you are making them include you in their plans. This is definitely a win-win situation for you.

These intimate questions are subtle in their essence but still don’t allow a man to feel bombarded with them because he will shut down his emotions and his mouth.

Slip these questions into the conversation and don’t use them all at once.

They will come up sooner or later and if they feel like a natural part of the conversation, you will get more sincere answers.

The 7 Most Intimate Questions You Could Ever Ask While Dating

The 7 Most Intimate Questions You Could Ever Ask While Dating