231. How to Ask Dating Questions

In this episode, I dive into why asking questions is both an art and a crucial skill on your dating journey after divorce. Most women I work with struggle not because they lack intelligence or communication skills, but because the drama attached to dating turns question-asking into self-sabotage.

You might think asking questions is straightforward, but are you using them to protect yourself or to people-please? Both approaches block authentic connection and prevent you from gathering the information you need to make wise decisions about potential partners.

Key Insights

• Curiosity is your superpower: Approach dating with curiosity—not just about your date but about yourself. Your reactions hold valuable information about your patterns.
• The protection trap: Going into dates with a rigid checklist of questions turns dating into an interview. You miss crucial nuance and context when you're focused on checking boxes rather than truly connecting.
• The people-pleasing pitfall: When you avoid asking important questions because "you don't want to be nosy" or "you don't want to chase him away," you sacrifice your needs for a stranger's comfort.
• Reclaim your authority: Dating involves meeting a stranger, knowing them for months, and potentially committing to them for life. This requires active participation, not passive acceptance.
• Your dating rights: You have the right to know about people who want access to you. You deserve to have potential partners earn your trust through honesty and transparency.

Practical Takeaways

• Start with broader questions about lifestyle, career goals, and weekend activities before diving into deeper topics
• Design questions based on your core values rather than using generic lists
• Pay attention to how someone responds—defensiveness, vagueness, or dismissal tells you something important
• Recognize when you falter in asking important questions and get curious about what's happening within you
• Remember timing matters—questions should match the relationship phase you're in

Dating After Divorce Wisdom

Think about it: we've known our siblings, cousins, and best friends our whole lives. Yet romantic relationships expect us to meet someone, know them for months, and commit to them forever. That's wild! Since this is our collective social agreement, we need to approach it with intention and courage.

Your Next Step

If you don't know what questions to ask, that's a sign you need clarity on your core values and relationship vision. This isn't just about having a list of questions; it's about knowing which answers matter specifically to you.

Ready to transform your dating experience? Book a consultation call with me where we'll discuss how working through your core values and dating patterns can help you find clarity and confidence. Stop outsourcing your safety to a checklist and start leading your own journey to love.

Schedule your Dating Consultation Call with Sade 

The Dating After Divorce Podcast with Sade Curry helps smart, accomplished women navigate dating with confidence after divorce. New episodes every Tuesday.

Transcript

How to Ask Questions When You're Dating

Tue, Apr 29, 2025 5:51AM · 28:03

SUMMARY KEYWORDS

Dating questions, self-sabotage, curiosity, emotional awareness, protective questions, people pleasing, relationship goals, core values, communication, assertiveness, relationship phases, emotional maturity, trust, partner selection, dating journey.

SPEAKERS

Sade Curry

Sade Curry 00:01

Hello everyone. Welcome back to the podcast. I'm your host, Sade Curry, and today I want to talk about asking questions when you're dating. Now, this might seem like a no-brainer, but I work with women every week for whom this point of asking questions when dating can be a huge obstacle, not because they're not smart, intelligent, beautiful, expressive and communicative, but because dating has so much drama attached to it that the way the question issue comes up ends up turning into somewhat a little bit of self-sabotage along the way, and so we're going to get into that today.

First of all, I love the idea of approaching dating with a lot of curiosity, not just curiosity about the person that is in front of you or the person that you are texting with, but curiosity about yourself, because curiosity is how we raise awareness about who we are, what's going on with us, what's going on in our emotions, where our growth spots are, and where we have patterns that are sabotaging this journey to love. So curiosity is huge, and I will always encourage my clients to be curious about what's happening, like, "Oh, I'm not attracted to this guy." Okay, let's get curious about that. Why not? Because you're going to force yourself to marry the guy, but because that lack of attraction holds a lot of information about you and about the person, and that information is so useful on the way to love.

So let's talk about asking questions. The problem that I see with the question asking situation is we're often trying to use asking questions as either a way to protect ourselves or a way to people please, and neither one of those things is useful when you're dating. When you're asking questions to protect yourself, because you're like, "Okay, I'm gonna go into this date with my 20 questions, and if he answers even one of these wrong I'm going to kick him to the curb." And so the date turns into an interview situation, and so you don't really get the information that you need because the questions were not asked in an appropriate setting, or you have questions the timing is appropriate. But then you start to people please, "I don't want to be nosy. I don't want to chase him away. I don't want him to think that I suspect him of something." And so you don't ask the questions that you need to ask and you people please your way into a relationship that ends up not being right for you.

Both of these situations aren't the way to use questions, and also, both of these situations are situations where you're not open minded enough to be curious and just see how things play out. In the situation where you are being overly protective of yourself, your brain has this belief that something bad is going to happen, and you have to prevent it at all cost, and you need to use these questions immediately to make sure that nothing bad happens.

And in the other situation, your brain, with people pleasing your brain believes that you're going to lose this person, or this person is going to be angry at you, and you're not gonna be able to handle that, so you can't ask questions, or you can't ask the real questions. You can't appear to be nosy, you can't appear to be assertive, because the worst thing that could happen is this person has a reaction to your questions, and both, like I said, both of those situations are not the way we use questions when you're looking for a partner.

Like the whole dating thing can be so crazy. Think about it. You have siblings, if you have siblings, people who've known you your whole life, cousins, best friends from high school. You have your parents. But romantic relationships are this really weird thing where you're supposed to meet someone, know them for like, a few months, and then hit yourself to them for the rest of your life, like that is insane. And since, as a collective society, we have all agreed to something that looks like that, whether it's marriage or partnership or companionship, you know, something that looks like that is our collective agreement right now, you have to not take things for granted, like asking questions and finding out what you need to know, plus observing the person is a huge deal, especially after divorce, we can't afford to make those same mistakes again.

So when it comes to asking questions, we cannot afford to be afraid of following our curiosity. You can't be afraid of another person's reaction. You can't be worried so worried about a stranger's comfort that you put your own emotional well being to the side. And I see this all the time, amazing, accomplished women, running businesses, raising children, you know, leading teams. When it comes to dating, we become these shy, you know, unassertive little girls. We think we're being pushy, right? We don't want to ask, "Hey, are you looking for a long term relationship?" And I know that some guys are gonna lie, but that's a different issue. This is about you asking the question.

"I don't want to seem pushy, I don't want to seem like I'm giving him an ultimatum. I don't want to seem desperate." And so you date someone for three months, you fall in love, only to find out that he had no plans to get married. Like, he's like, "Oh yeah, no, I'm not doing marriage again, but I do like having you around" like that's not going to work, or asking about finances, finding that people have debt, right? You know, we just never find the right time to ask or the right time to follow up, or asking follow up questions to some of the things that we know we're like, "Okay, this is kind of your situation. What's going on there? What are your plans with that?"

Whatever your situation is with questions. Or here's another scenario that I've seen people say, "I don't know what questions to ask." We have to resolve this. Whichever bucket you fall into, it has to be resolved.

For the people who are, you know, you have so much concern or fears around dating that you are protecting yourself with, I don't want to say overly aggressive questions, but questions that you're not even listening to the answers for, questions where you're not observing the person you're just like, "Okay, these are my 20 questions. If he answers them, all right, we're good. If he doesn't, then we're bad." Versus a more open process where you're listening, you're watching, you're checking in with your emotions.

That means that deep down, you probably believe that you cannot handle this dating situation. You can't handle it, you're afraid that you're going to make the wrong decision, and you are outsourcing that safety or your capacity, or your ability to handle whatever comes to this list of questions. You have a list of questions, and you think that list of questions is going to save you from, you know, something bad happening in the future.

And here's the thing, you could meet someone who is an accomplished liar, who answers all your questions correctly, and you could meet a good person who is just not like on the ball, who answers some of your questions in a way that's like not exactly what you're looking for, but because you have your guard up and you're outsourcing your decision making to the question list. You're not able to take a step back and say, "Okay, there's some nuance here. There are things that I need to verify this person has answered all the questions correctly, but I am going to take my time and observe and see what actually happens and verify these things are true. Or this person answered this question in such a way. Let me follow up with, you know, figure out what is going on here."

And I'll give an example with one of my clients, who was looking for someone on the same political side that she was, and she met a guy in person, and, you know, they hit it off. And he, you know, asked her out, asked for her number and was going to follow up with her. And then when she, you know, came to our call and was talking about it, she was like, "Yeah, he told me where he lives, and that pretty much means he's on the other side of the of the aisle." And I was just like, like, why didn't you just ask? Like, you could just ask in that moment, but her brain was so protective that she was like, "Okay, if a person lives in this city, then that means they're like this. If they live here, then that means they're like that." And her brain was so shut down by being so self-protective, because it was so worried she would end up with someone who didn't believe what she believed, that it didn't even occur to her to just ask the question, either in person or via text. And I was like, you can just ask, like, you have nothing to lose, especially since you've made the connection and things are going well. Just say, "Hey, what do you think about this issue?" Or send him something from the news and say, "Hey, this happened today. What are your thoughts on this?" And then let him show you who he is versus you assuming who he is.

On the people pleasing side, I know a lot of women who struggle to ask direct questions. Like that is not uncommon at all. And this comes from the good girl training. This comes from how women are socialized to be nice, to not make anyone feel uncomfortable, to not make anyone feel...

Sade Curry 09:46

...you know, any kind of discomfort. So don't be bossy. Don't be intimidating. Smile and nod. Don't speak up. Don't say anything that makes anybody mad, even though you may not know exactly what's gonna make anyone mad. You're just supposed to intuitively know this and avoid any kind of discomfort in other people. And you know, if you are like me and many other women, you were sort of like conditioned from the time you were born to do this.

Many women were raised to believe that even questioning a man or questioning a man's thoughts or disagreeing was disrespectful. I know in my culture, disagreeing with an adult was considered so disrespectful, whether it was a man or a woman, right? And when you're surrounded by adults every day, you really become conditioned to know, to think that, like asserting your own thinking is a bad thing, right?

Some people received, you know, messages that men don't like women who say this, men who don't like women who act like that. I know, I definitely, you know, got that I was a talkative child and a thinking young woman, and people are always like, you know, don't be aggressive and don't be disagreeable. So it's an instinct that's kicking in. This is not something that you are, quote, unquote, doing wrong. You are not doing it wrong. There is nothing wrong with you. This is just the water that we swim in. This is just the world that we live in.

And even though the world is that way, you can change your own individual experience, and that is the only thing you can do. You cannot. We can move towards a better world, but you're not going to change the world, probably in time to meet your person. Like we're moving towards things being better. We're working on it, but it's not an overnight thing. So if you do want companionship, if you do want to meet someone to spend the rest of your life with, that's something you're going to have to create that micro experience for yourself, and it's going to take you looking at yourself and being aware of your own responses, being aware of how you display these patterns when it comes to asking for information that you need to make a decision.

You know people will talk about like asking for what they want in relationships, and I find that like what they're really doing is like being extremely shallow about what they're using to determine that a person is right for them. It's like ask for what you want. So after the third date, people start asking for "I want you to text me every day, and I prefer that you text me and call me, and I prefer that you do this, x, y, z" and that really doesn't help you very much in identifying who is the right person for you, because a man can text you every day and still all he wants is a hook up like that. Can that can be true. And you know, many people know that that is true. A man can text you every day and even call you every day and have no intentions for a long term relationship.

So we have to take back the responsibility of figuring out the person that you're choosing. It's not that person's responsibility to help you choose the right person. It's their responsibility to choose the right person for them. It is your responsibility to choose the right person for you, and that means asking what you need to know, bringing up topics, even if those topics are uncomfortable. Now, I'm not talking about, you know, talking about family histories of trauma on the first date. I just mean this kind of, like as a journey with a particular person, you know, week one, week two, week three, kind of laying it out.

But when you've, if you've been in a divorce situation, or you were in a toxic marriage, you probably have a habit of walking on eggshells, right? You know what it's like to ask your spouse something and have that just blow up in your face, like them shutting down or getting angry when you're like, bringing up things that are important, that are important to the family. They're important to the health and well being of the family. Some people have exes who would explode if they asked about money, or if they asked about what he was doing, or if they dug deeper into his past, like that. I know can really be a trigger for some people.

When you get back, you know out to dating and that trauma response is very, very real, but the first step is understanding that you even have that. Because if you spend all your time avoiding questions and hoping that somehow you can rely on the other person to lead the relationship and tell you what you need to know, then you know you're putting yourself at risk. It's better to say, "Okay, here's what I need to know, and I'm going to try to ask it."

And if you get up to the moment of asking the question and you falter, or you don't ask it, that's not a thing to be shameful about. That's a thing to observe, to get curious about with yourself. "Oh, I meant to ask him about this. Yeah, and I didn't, I wonder what's going on with me," and that gives you two things. One, it puts you in a position where you are growing, your awareness is growing, and you see the challenges that you have with dating, and you can start to fix that. Again, I encourage you to come work with me to deal with some of these more underlying things, so it helps you with your growth, because dating is such a growth journey.

And then secondly, it gives you a running start to do the things that you need to do. So like, you know, this happened with a client of mine who need, she wanted to ask about exclusivity, because she'd been dating this guy for several months. And she was like, "Okay, I don't know if we're exclusive or not, and I want to bring this up." And she took, it was probably five running starts at that question, but she'd never done this before, and so it didn't come easy to her. She had some anxiety about it.

And every week I would say, "Okay, this is the week when you see him, you need to ask about exclusivity." And we would work on the phrasing that was comfortable for her and how she wanted to say it. And lo and behold, next week, she still hadn't asked him, but that was fine, because she took all those running starts, and eventually she asked the question that she needed to ask, and she got the answer that was available.

So it's important to use questions and curiosity to find out where you have people pleasing tendencies, where you have anxious tendencies, where you're walking on eggshells with the people that you date, or to find out where you are being overly protective of yourself and not being curious enough, where you're putting up walls versus being curious and really getting to the answers before making a decision.

And then the third thing with asking questions is knowing what questions to ask, and this is different for every single person. So when I do the core values exercise, which is included in the Captivate dating profile system. So if you get that, you will have this core values process in there. When I work with my clients on their core values, which is what we use to create their blueprint for dating, that information is what we use to determine what questions they need to ask.

Now there's some basic questions that are good for everyone, and that's included in the dating cheat sheet, also included in the Captivate dating profile system. As a bonus, there's some basic questions that everybody gets in the dating cheat sheet about work and family and things like that that really just help you open up that small talk, but beyond that first few messages of texting that gets you to the first date, you have to start using your own values, the things that are important to you to ask questions, not just a list of questions that you download from from the internet, because the list of questions that you download from the internet might be nice, but they might not get to the answers that are important for you.

The questions you ask have got to be based on the relationship you want, the person that you are, your specific family dynamic, your own partner list, the life you want to live. And so it's so unique, and it's so context based, that I always want to remind everyone it's not a formula. You cannot date with a formula. If you date with a formula, you will get random results, because you're using things that apply to everybody. But you are a unique person looking for a unique person who is the right person for you. So

Sade Curry 18:36

if you don't know what questions to ask, you might need to do some work to get that again. I encourage you to get the Captivate dating profile system. We go through your core values. We go through your attraction indicators. We go through your relationship vision like it is a whole course in there, and you'll have ideas for questions to ask in there. Or you can work with me. You can book a consultation call with me. The link is in the show notes, and we can talk about how working with me through your core values and your dating can help you get out of this place where it's like, "I don't know, I don't know the questions to ask."

It is important and very self-protective of you to know, and there's nothing wrong with not knowing, but staying in a place where you don't know is neglecting yourself. You are neglecting your own journey, right? You have a right to know about people who want access to you. You have a right to have them earn your trust by being honest and truthful and transparent, right? So you have a right to know it's okay for you to ask questions if a person is uncomfortable with you asking questions that has nothing to do with you, that has anything to everything to do with them.

So you have a right to know what you're getting into with this person. You don't want to waste months with someone who has no intentions of having a real relationship, like we've done that before. When I'm gonna do that again, on a practical level, I encourage you to start with when you're dating, to figure out questions that you want to ask. Start with the big picture questions, right? Like, don't go too narrow too quickly. Don't go too deep. Don't ask for a person's bank statement on the on the third date, right? But start with the big picture. "What are your thoughts about retirement if you're getting close to that age, or where do you see your career," like just things like that. "How do you spend your weekends? What's important to you in a relationship, like, what are your hobbies?" General is better earlier?

Now, of course, we can also target general questions to fit with your core values, but start with broader questions, and then you can follow up, either on the spot or later to more specific topics, right? So if someone says, "Oh, I have adult children," and they say, "Oh, do they live in town, or do they live out of state?" And then they tell you a little bit about their children. Then maybe on the third date, you can ask, "Are you close to your children? What kind of relationship do you have?" If, as the relationship naturally progresses, then the questions will naturally get more and more specific.

I always encourage my clients to have, you know, their own questions for every gate of the relationship. So we do relationship gates where you each woman designs how she wants to pace the relationship, and so I help them design the right questions that match their core values and that match the phase of the relationship that they're in.

Right I really just, I do not like generic questions. I have lists of generic questions. You on the internet, there's generic questions and stuff, but if you are actually pursuing a real relationship, generic questions don't help you unless you've agreed with the person. "Okay, wait, we got a stack of questions. We're going to tackle these questions together," which is kind of fun, right? So it's more like you're doing these, uh, you're doing you're either doing a couple cards, like both of you have agreed to work through those questions. Otherwise, it's really better to have questions that fit you, because when they'll be easier for you to ask too, you'll be able to bring them up in a more organic in a more organic way, and then you also have an idea of what questions are important, like relationship goals, family dynamics, past relationships, some of these things are more important to some people than others, right?

Like I had a client who has a special needs daughter, so the questions around family dynamics that she asked were very different from someone who was an empty nester and who was dating other empty nesters. Timing is important. You want to you want things to be organic, and at the right stage, you got to feel your way into that. But also you don't want to be like, "Well, I just don't know the right time." And now it's six months later, and I haven't asked, you know, the basic questions.

And finally, pay attention, right? Just pay attention to the answers to the questions. Don't don't just check off the box. Watch the body language. Take your time, even if you don't get the the true answer in that moment, that non-answer is a kind of answer. There's information in there. So watch if they get defensive or angry. Watch if they turn the questions back on you, if they give vague responses, or if they dismiss you, or if they argue that you're, you know, you shouldn't be asking questions, and then you can create some awareness. They're like, "Okay, what's going on here again?"

Don't rush to make a judgment of them or make a judgment of yourself the situation itself contains all of the information you need, so don't take any of it personally. Again, you want to just get curious. Don't worry that he'll think you're interviewing him. Listen, this is your journey. You are the CEO of your journey. Don't worry they're gonna scare away a good person. Like a good person is also like wanting to know if you're right for them. A good man is also wanting to know if you are the right woman for him. So he will be asking thoughtful questions as well. He will be, you know, trying to say, "Okay, what's going on here? I want to know if this person is right for me."

Don't worry about seeming desperate or rushing things, right? Like, if this is what you need to know at that stage, then that's just what you need to know. And don't worry if the conversation feels unnatural and forced. Listen, a lot of things about dating feel unnatural and forced. Like I said at the beginning, we're meeting up with perfect strangers and trying to evaluate them for lifelong companionship. Okay, that's a lot, right? And so having a game plan is going to help you sort of bring that tension down and bring that awkwardness down.

So having questions that you're going to ask, prepping yourself for questions that you're going to ask, will actually make it a little more natural. Over time, the first time might be hard. I get it if you if you haven't dated a lot, the first few times might be a little awkward, but that's just life. Everything is awkward. When we start out learning the art of asking questions will save you so much time when you are dating, you will be able to move on quickly from people that are not right for you, without being overly dismissive or overly protective, without walls, you'll be able to build better connections, right because when you do ask the questions to the right people, even if that person doesn't turn out to be the person you eventually stay with, you're having more fun because now you're having better conversations.

You will attract emotionally mature partners, because emotionally mature people are okay with questions. They understand the social contract. They're okay with being authentic and open, and they want you to be authentic and open. You will become the person who leads your own journey. You are in charge of your journey like you cannot meet a stranger. And I just shake my head when I see things on the internet that imply this, like, you're going to meet a man on on an app and like, within two weeks, he's going to be the quote, unquote leader, leading you and pursuing you. I'm like, You do not know this person, honey.

You don't like there will be no leading until trust has been earned and a relationship has been established, and we know what's up, right? You are in charge of your journey. You are a sovereign being. You are the boss of your life, and you need to own that. You need to take that responsibility. It is your job to protect yourself. It is your job to care for yourself and reclaim that space in your own skin. And when you practice these you're going to meet the right person sooner. It just accelerates your journey, because every time you get answers and you reflect on them, it will help you clarify what you're looking for. It will help you clarify what you're not looking for.

Sometimes we get all the answers we want. I've worked with clients where they had a checklist and everything, and they were like, "He's everything on the checklist, but he's not the right guy." And that can happen. It's hilarious when that happens. It helps you refine your partner list in a way that makes it more useful. It helps you get rid of preconceived notions, because you're meeting different kinds of people, and you're like, "Oh my goodness, the things that I thought were important to me may not be as important, and my preconceived notions are actually being debunked."

You will become a more flexible, open, nuanced person, which is just another step in maturity, and you will accelerate your journey to your perfect match who is waiting for you when you grow and build the courage to ask the right questions and to stay in the journey until the right person connects with you. Okay, that's it for today. I want to thank you for your time and attention, and I will see you next time you.