Serious dating questions to ask

We learn to protect her and provide for her; we learn about the basic core of love for a woman from her. Indeed, if a man is at odds with his mother, it's a safe bet that he's going to be at odds with you. If you hear any part of "Man, me and my mother? We just don't get along. After you find out how he feels about his mother, ask him about his father. If he had a great relationship with his dad, then he was probably raised with a core set of values that he'll bring to your potential home together. Now, I understand that a whole host of men grew up without fathers in their households, but chances are that the man you're interested in had a male role model in his life who showed him the ropes of manhood, or perhaps the absence of his own father taught him a few things about what he doesn't want to do when he becomes a father.

30 questions to ask a guy you're dating to get to know him better

At any rate, ask questions about his relationship with his father, and his answers are bound to reveal the kind of father he just might turn out to be. You're also going to have to ask him about his relationship with God. Let me be direct: After all, what moral barometer does he answer to if not to God? What's going to make him even consider being loyal to you? What's going to make him do right by you and the kids? What's going to make him feel whole? I'm not saying that you shouldn't date a man who doesn't go to church, or who has a different belief system than you. But if his core beliefs don't match up with yours, you're likely to have a problem.

These next two questions should be asked after you've been talking and dating for a while. Ideally, ask them before you have parted with the cookie y'all know what I mean. If you have already had a sexual encounter with the man, you can ask these questions anyway.

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The answers may hurt a little bit more, but at least you'll know. Now, this one you'll have to ask after a few dates, because he's going to need time to get to know you. But his answer will be critical because it will reveal to you what his plans for you are. If you've been out on a couple of dates and you've had lots of conversation, you know something about him, but what's more important, you want to know what he is thinking about you. You have a right to know.

Questions to Get to Know Someone

He was attracted to something—he liked your hair, your eyes, your legs, your outfit. He didn't walk over there just to be walking. Beyond the initial attraction, however, men pretty much know if you're the kind of woman they're going to sleep with and keep it moving, or if they're going to stick around and see if they want more. This, you will be able to tell by his answers. Listen to his answer closely. I assure you this is how it will go, because every man will answer this question the same exact way: I think you're the kind of woman I could see myself with," all of that generic stuff we know you want to hear.

Still, this isn't the answer you should be looking for. You want to know that he's really thought about you beyond the surface. So do the follow-ups. What about me makes you think I'm kind? But if he says, "You remember that time when it was my mom's birthday and you called me and reminded me to pick up a card for her? That was really nice.


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The level of his specifics will give you yet another clue into this man's intentions for your relationship. If he can give you specifics, it means he's been listening and adding it up—he's determining if he's going to keep you, if he can see himself in a committed relationship with you.

And that could mean that you're at least on the same relationship page. Now this is not to be confused with what do you "think" about me—"think" and "feel" are two wholly different things. And if a man cannot tell you how he feels about you after a month of dating, it's because he doesn't feel anything for you—he just wants something.

Ask a man how he feels about you, and he's going to get confused and nervous: You cut him right off and say, "No, no, I want to know how you feel about me. But you'll have to get him to answer it. Don't get upset if he doesn't answer right away: Men do not do emotion well, at all, and expressing it doesn't come easy. He can answer questions about God and the kids and his mother, but with this question, you're asking him to look into his soul, and our DNA isn't made up for the heartfelt outpouring to just anybody.

But this doesn't mean you should let up. What you're looking for in his answer is something like this: He may not be in love with you just yet, but he's crazy about you and he's probably thinking he wants to explore a long-term commitment with you, because when he starts to profess and put you in a position where he can provide for and protect you, he's seeing a future with you in it.

And this is exactly where you want to be with this guy. The "I think you're cool" answer isn't going to cut it here, ladies. And if, after you've asked the question and probed deeper, you realize his feelings for you don't run very deep— that he's just not there—then you need to not be there, too.


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  • Pump the brakes until you start hearing and feeling from him the things that you think are important to hear and feel from a man with whom you're willing to forge a relationship. You may not necessarily like the answers, but he's going to answer them. If he refuses, then don't bother with him.

    Empower yourself—it's your right to know all of these answers up front; per my ninety-day rule, which you'll discover in the next chapter, you need to ask these questions within the first few months of a courtship. You can ask them for clarification. Or you may need to ask them with the hope that they'll solidify what you may already know—either that you need to get out of your relationship or that you are headed in the right direction.

    Or they may make you say, "Wow, I'm glad I'm with this man. Know, too, that though we'll answer the questions because we like talking about ourselves, our answers just may make us consider the woman who's asking the questions in a different light. We definitely want to know where our women stand on these issues, too, but we're not going to bring it up—especially if our intentions for you aren't pure.

    But in your conversations around these issues, your man just might learn something about you, too, something that makes him know he's got a pretty solid woman on his side. Level 2 can happen naturally as you live with someone, travel with someone and have shared experiences. But Level 3 only can be done purposefully—with the right questions in a safe space.

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    This brings me to the 36 couple questions. Social psychology researcher Arthur Aron of the Interpersonal Relationships Lab at Stony Brook University in New York developed 36 questions to help people break through each of the intimacy levels.

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