Stop Wasting Time: Ask These Questions Before Getting Attached
Send us Fan Mail S1 E4 — What to Ask on Early Dates (Without Interviewing Him)Season: 1 Episode: 4 Length: ~31 min Episode Summary Some of us show up to first dates with 17 questions and the energy of an assistant principal running an investigation. Others leave knowing his favorite vacation spot and nothing about his character. 🙃 In this episode, we find the middle: the conversation doors that tell you who he really is, how to listen beneath ordinary answers, and a simple after-date reflect...
S1 E4 — What to Ask on Early Dates (Without Interviewing Him)
Season: 1 Episode: 4 Length: ~31 min
Episode Summary
Some of us show up to first dates with 17 questions and the energy of an assistant principal running an investigation. Others leave knowing his favorite vacation spot and nothing about his character. 🙃 In this episode, we find the middle: the conversation doors that tell you who he really is, how to listen beneath ordinary answers, and a simple after-date reflection that helps you decide whether he's earned another date.
What You'll Learn
- Why the goal of an early date isn't deciding whether to marry him. It's deciding whether you have a wise reason to know him better
- How I used to screen for an enjoyable date instead of a dependable husband (and confirmed a man was "fun, employed, and moisturized")
- Why better follow-up questions beat more prepared ones
- What "How was your day?" reveals about how he handles frustration, and the eyebrow-raiser when every story has a villain and it's never him
- How his typical week shows whether his life actually has room for a relationship (and why tagging along isn't the same as being prioritized)
- Why you ask what he's looking forward to with this relationship, not whether he wants marriage someday
- The follow-up to "Do you have a relationship with God?": What does it look like on a Monday?
- What his vision of a healthy marriage says about what he plans to give, not just what he expects to receive
- Why "What kind of life would you like to build?" beats "Where do you see yourself in 5 years?"
- How scripture shapes the posture: quick to listen (James 1:19), no answering before you've heard (Proverbs 18:13), and knowing people by their fruit (Matthew 7:16)
- Why your dreams don't have to be identical, but they can't require opposite lives
The Questions (Conversation Doors, Not a Script)
Open the ones that fit naturally and follow the conversation:
- How was your day? Listen for emotional responsibility.
- What does a typical week look like for you? Listen for whether there's room for you.
- What are you looking forward to with this relationship? Believe what he says, and don't add subtitles.
- Do you have a relationship with God? Then: What does that look like on a Monday?
- Have you been around healthy marriages? What does a healthy marriage look like to you?
- What kind of life would you like to build?
The Purpose Pause
Before you start rehearsing these in the mirror (yes, I know you're going to), answer honestly:
- Are you genuinely trying to know him, or performing so he'll choose you?
- Are you listening to understand him, or waiting for your next chance to impress him?
- Are you being honest about your values, or adjusting your answers because you already decided you like him?
- Are you observing what he's offering, or building a future in your head before you have the facts?
This Week's Homework
For your first 4 dates with a man, do a short reflection after each one. At home, in your quiet time. Not in the restaurant bathroom.
- What did he say? His actual words about faith, relationships, marriage, family, and the life he wants. Don't paraphrase his uncertainty into potential.
- What did I observe? Did he follow through? Was he respectful and curious about you? How did he talk about other people? Did his behavior support his words?
- How did I show up? Were you relaxed and honest, or did you perform, interview him, or shrink your values?
- Is what he's offering aligned with what I want? Not "Is this my husband?" but "Do I have a wise reason to accept another date?"
After date 4, review all four entries together. Are his words and actions pointing the same direction? Is he getting clearer, or staying conveniently vague? If you still don't know what he's offering, have a clarifying conversation: "I've enjoyed getting to know you. What are your thoughts about where this is going?" Then listen without rewriting.
Join the Conversation
Sis, if this episode helped, here's how to keep the fam growing:
- Subscribe on Apple Podcasts, Spotify, or YouTube so you never miss an episode
- Leave a review and tell us which question you're trying on your next date
- Share this with a Sista who already has her first-date questions organized by category and level of urgency 💛 (We love the preparation. Please let the man finish chewing.)
Date with purpose, and build the marriage God is calling you to.
Listen & Follow
- Listen to the podcast: https://www.lessadavis.com/
- Watch on YouTube: https://www.youtube.com/channel/UCBRbMgJFL5YvzIToplDbtgg
- Instagram: https://www.instagram.com/datingwithpurposepod/
- Threads: https://www.threads.com/@datingwithpurposepod
Quick question, Fam: Have you ever liked a man and still wondered, “Okay, but is this actually going anywhere?”
I made something for that exact moment. My free guide, I Like Him… But Is This Going Anywhere?, helps you look at what he’s said, what you’ve seen, and what you may be filling in yourself. It even gives you the words to start that clarity conversation.
Get your copy at LessaDavis.com.
What would dating with purpose look like for you this week?
00:00 - Dating with purpose tips
04:24:47 - Evaluating a new relationship
07:07:47 - Early dating conversation tips
11:56:47 - Evaluating a guy's weekly schedule
16:54:47 - Assessing a partner's faith
18:03:47 - Examining relationship expectations
22:47:47 - Reflecting on dating intentions
25:26:47 - Assessing compatibility after multiple dates
29:54:47 - First date tips and advice
You do not need to know whether that man is your husband by the time the check comes. You need to know whether you enjoyed yourself, whether you've learned something real about him, and whether what he is offering deserves another date. That's it. Because some of us are showing up to first dates with 17 questions, three deal breaker lists, and the energy of an assistant principal conducting an investigation. Where do you see yourself in five years? Ma'am, he came for tacos. Why are you asking for his strategic plan? But then some of us go to the opposite extreme. We laugh, flirt, admire his swag, and leave knowing his favorite vacation spot. But nothing about his character, his relationship with God, or whether he is emotionally available. So today we are finding the middle. How do you relax, enjoy the date, and still gather the information you need to date with purpose? Come on, because today we are going to talk about it. You are learning how to choose wisely and how to let God lead you while you do it. Today we are talking about what to ask on early dates when you are looking for marriage or a committed relationship. And before anybody pulls up a note on their phone titled Questions to Ask My Future Husband, let me make something clear. I am not giving you a script to read across the dinner table. This episode is about curiosity, not integregation. It is about learning how to have a natural conversation. Listen beneath the surface, and pay attention to whether his answers and actions remain consistent over time. So take a breath, put the clipboard down. Girl, have fun. Let's get into it. Back when I was dating, I asked the typical questions. What do you do? What do you like to do? Do you have kids? I wanted to know whether we had similar interests. I wanted to know if we, you know, could have a good time together. And if I'm telling the whole truth, I was also trying to determine whether that man has some swag. You know, could he dress? Could he talk? Did he walk into the room like he belonged there? Was there a little seasoning on that situation? Those questions weren't wrong. Shared interests matter, attraction matters, enjoying a man's company matters. But those questions did not tell me whether he could build and sustain a healthy marriage. I was screening for an enjoyable date, not necessarily a dependable husband. And I think a lot of women do that without even realizing it. We leave saying the date was amazing. Okay, what made it amazing? We like the same music. We both love to travel. We laughed all night. He has a great job. And girl, he smelled good. Wonderful. We have confirmed that he is fun, employed, and moisturized. What else did you learn? How does he handle frustration? Does he take responsibility for his choices? Does he have an active relationship with God? Or does he simply know how to say that he is a Christian? Does his current life have room for a relationship? What does he believe marriage requires from him? What kind of life is he trying to build? And here is the question we often forget while wondering whether he likes us. Do I like what I'm learning about him? Fam, you are not there to earn a callback. You are not auditioning for the position of girlfriend. You are two adults learning whether there's enough mutual interest, alignment, and character to continue. That brings us to the reset. The answer is not to replace shallow conversation with a first date deposition. Dating with purpose does not mean sucking every ounce of joy out of dating. It means knowing what you are listening for while you enjoy the person in front of you. You will not know if he is the one on date one. I know that is not exciting. It does not come with violins, a prophetic dream, or a slow-motion shot of him walking through the restaurant. You do not have enough information yet. And honestly, he does not have enough information about you either. The goal of an early date is not to decide whether to marry him. The goal is to decide whether you have a wise reason to know him better. Let me say that again. You are not deciding whether to marry him. You are deciding whether you want to know him better. That should take some pressure off. I hope so. You do not need to force every major topic into one meal. You do not need to ask about his credit score before the bread arrives. You do not need his childhood wounds, retirement plan, preferred number of children, and position on private school before dessert. Early dating should have room for laughter, stories, attraction, playfulness, and a few questions that open the door to something deeper. I did a little research. And the research on conversation gives us a useful clue here. People tend to respond well to someone who asks questions, especially follow-up questions. Because follow-up questions communicate that you are listening, understanding, and interested. I just dropped y'all a gem right there. The key is not asking more prepped questions. The key is asking better follow-up questions. A checklist says, I need to get through my questions. Curiosity says, I want to understand the person sitting in front of me. And scripture supports the posture that we need. James tells us to be quick to listen and slow to speak. Proverbs warns us about answering before we have truly listened. Jesus teaches us that people are recognized by their fruit. So yes, ask, but listen. And after you listen, observe. Because discernment is not just hearing a good answer. Discernment is watching whether his life agrees with it. Now let's talk about the actual questions. These are not seven questions you must complete before the server clears the table. These are conversation doors. Open the ones that fit naturally, walk through them with genuine curiosity and pay attention to what you find on the other side. All right, first question. How was your day? Yes, that simple. You do not always need a deep question. Sometimes you need to listen more deeply to an ordinary answer. When you ask, how was your day? Listen to how he talks about frustration. A mature man can admit, I was irritated, the situation did not go the way I wanted, here is what I did to resolve it, or here is what I had to accept so I could move forward. He does not have to pretend everything is wonderful. We are not looking for a man who smiles through every problem like he is trapped in a toothpaste commercial. We are listening for emotional responsibility. Can he name what he felt without making everybody else responsible for what he does with that villain? My eyebrow goes up when every story has a villain, and somehow he is never it. His boss is stupid, his coworkers are lazy, his ex is crazy, the waiter is incompetent, traffic has apparently launched a personal attack against him. One bad day does not define a man. Look for a pattern and a posture. Does he solve problems or just collect people to blame? Can he accept that what is out of his control and move forward? Can he speak about people with basic respect, even when he disagrees with them? Do not listen for a man who never gets frustrated. Listen for how he handles frustration and whether he takes responsibility for what happens next. And pay attention to whether he asks about your day, too. You should not finish a two-hour date knowing his entire organizational chart while he still knows nothing about you or what you do for a living. Curiosity should travel both ways. All right, let's get to the second question. What does a typical week look like for you? This question is sneaky good because his calendar may tell you more than his dating profile. Listen for what consistently receives his time. How does he approach work? Does he have friendships and family relationships? Does faith exist anywhere in his normal rhythm? Does he rest? Does he have life structure? Or is everything an emergency? And most importantly, does his life have room and flexibility for a relationship to grow? A full calendar does not automatically make a man unavailable. Work, church, volunteering, travel, and time with friends can all be healthy. But even good things can crowd out the relationship he claims he wants. If every minute of his week is booked and nothing can ever shift, where is this committed relationship supposed to live? And the seven minutes between Bible study and baggage claim? Do not judge only by his description. Observe what happens when the two of you begin making plans. Does he occasionally rearrange something non-essential to see you? If he cannot change an activity, does he suggest a specific alternative? When it becomes appropriate, does he invite you into parts of his life? And let me add one caution: tagging along is not the same as being prioritized. If he only invites you to plans he has already making, you may be convenient. A growing relationship needs both opportunities to join his world and time he intentionally creates for the two of you. A relationship cannot grow on leftover time and last minute invitations. All right, next question. What are you looking forward to with this relationship? Notice I did not ask, do you ever want to get married? A man can want marriage one misty day in the future and still have no intention of building toward it with you. Ask about this relationship. What are you looking forward to with this relationship? Then listen to what he actually says. Most men will be straightforward when you give them room to answer. Believe the words you hear and do not add anything he did not say. If he wants commitment, he will usually communicate some form of direction. He may say he wants to continue getting to know you intentionally. He may say he is dating toward marriage. He may mention exclusivity as a future step if the two of you remain compatible. He does not owe you a commitment on the first date. Both of you are still gathering information. That is why I'm seeing where this goes can be tricky. It can mean I want a committed relationship and I'm taking time to see if we are compatible. Or it can mean I will enjoy your attention for as long as this is easy, but I am not moving toward anything. His actions will help define his words. Does he plan dates? Does he initiate consistently? Does he follow through? Does he ask questions that help him know you? Does the connection gradually become clearer? You do not need commitment on date one. You do need evidence that he is capable of moving toward it. And please do not add subtitles. He never said. If he says, I'm just having fun, do not translate that into he secretly wants a marriage, but he is afraid because no woman has ever loved him properly. And apparently I have been assigned this ministry. No, ma'am. Episode three was called Stop Filling in the Blanks for a Reason. Go check it out. Ask the question. Listen to the answer and do not ask up titles he never said. Question four. Do you have a relationship with God? Straight up. Straight up. This matters to you. So you do not have to hide it inside a theological scavenger hunt. Ask him, do you have a relationship with God? But understand that yes is the beginning of the conversation, not the evidence. Most people know the socially acceptable answer, especially when they know they are talking to a Christian woman. So follow up with one of my favorite questions. What does your relationship with God look like on a Monday? Sunday can tell you where he attends church. Monday starts revealing how he lives. Does faith influence his decisions? Does he pray? Does he engage scripture outside of church service? How does he respond when he feels distant from God? Can he describe a time when God corrected or changed him? You are not listening for a perfect spiritual routine. A polished speech about waking up at 4:30 in the morning to read Leviticus in Greek does not make him marriage material. You are listening for an honest, lived relationship with God. And then you are watching for the fruit. Does the way he handles pressure agree with what he says he believes? Does he accept correction? Does he respect your boundaries? Does his faith produce humility, self-control, love, and responsibility? Do not just ask where he goes on Sunday. Ask what his faith looks like on Monday. Question five. Have you been around healthy marriages? Then ask, what does a healthy marriage look like to you? This reveals both his exposure and his expectations. Who shaped his picture of marriage? Does he have healthy married people around him? How does he describe leadership, partnership, communication, and responsibility? I would be encouraged to hear him talk about praying together, listening to his wife, bringing her decisions that affect the household and communicating honestly. I want to hear what marriage requires of him, not only what he expects from a wife. Now, if he says he wants a wife who stays home with two children, that alone is not a red flag. That may be a beautiful arrangement when both people freely desire it. The eyebrow goes up when his entire vision describes her assignment. She stays home, she raises the children, she keeps the house, she supports his dream, she protects his peace. Okay, sir. What do you do besides bring home a direct deposit and request quiet? Can he describe how he will serve, sacrifice, listen, parent, lead, and make room for his wife's God-given purpose? A woman staying home is not the problem. A one-sided vision in which she has a detailed job description and he merely has a title. Now that is the problem. Ask, what kind of life would you like to build? What does that look like? His answer may naturally reveal how he thinks about marriage, children, career, finances, location, travel, ministry, service, stability, and community? You are not checking whether every detail matches your plan. Plans change, jobs change, cities change. God may redirect both of you. You are listening for direction, values, and compatibility. Does the future he described have room for a wife with her own gifts? And calling? Does he want children when you do not? Or does he not want children when motherhood is central to the life you desire? Does he dream of moving every two years while you want deep roots near family? Does he feel called to full-time international missions while your purpose requires you to remain local? None of these answers makes either person bad. They may simply mean the two of you are trying to build different lives. You do not need identical dreams, but your dreams cannot require opposite lives. Now, before you save those questions and start rehearsing them in the mirror, because yes, I know you're gonna do that. We need to pause because the most important question on the date may not be the one you ask him. It may be the one you ask yourself. That's right, sis. It is the purpose pause. Stop listening for a moment and answer this. When you go on a date, are you genuinely trying to know the man, or are you performing so he will choose you? Are you listening to understand him? Or are you listening for the next opportunity to impress him? Are you being honest about your values? Or are you adjusting your answers because you already decided you like him? Are you observing what he offers? Or are you mentally building a future before you have enough facts? The date is not only revealing him, it's revealing you. You cannot discern clearly while performing. You need to be present enough to enjoy yourself, honest enough to let yourself be known and grounded enough to accept what you learn, even when the answer is not what you hope for. You do not need to make a final decision during the date. Enjoy your meal, laugh, pay attention, go home safely. Then, when the chemistry is no longer sitting directly across from you, smelling good, take a few minutes to reflect. For your first four dates with a man, complete this short reflection after each date. Not while you were still at the table, and please do not excuse yourself to the restroom and begin grading this man. When you get home and have a little quiet time, answer these four questions. First question: what did he say? Write down his actual words, especially about faith, relationships, marriage, family, and the life he wants. Do not paraphrase his uncertainty into potential. Do not write he is open to marriage. If what he actually said was, I do not know if I ever want to get married. Record what he said. Two, what did I observe? Did he follow through? Was he respectful? Did he show curiosity about you? How did he speak about other people? How did he handle inconvenience? Did his behavior support the things he told you? And number three, how did he show up? Were you relaxed and honest? Did you enjoy yourself? Did you express your real opinions? Or did you perform, interview him, minimize your values, or try to become the answer you thought he wanted? Number four, is what he is offering aligned with what I want? Not is this my husband. Ask, based on what I know today, do I have a wise reason to accept another date? Repeat this after the first four dates, then review all four entries together. Now, why four? Because one date gives you an impression. Several dates begin to show consistency. Four dates are not a magical deadline, and four weeks are not a relationship law. Think of that point as a checkpoint. Do his words and actions consistently point in the same direction? Has the relationship shown some progress? Is he making space for you? Is he becoming clearer or remaining conveniently vague? Remember, he is still putting his best foot forward. So if his best foot is already late, vague, negative, and inconsistent, sis, please do not wait around to meet the other foot. If you reach four dates and still do not understand what he is offering, have a clarifying conversation. I've enjoyed getting to know you. What are your thoughts about where this is going? Then listen without rewriting. What did he say? What did I observe? Now, I know this can sound like a lot when all you wanted was to put on a cute outfit, eat something good, and see if you like the man. But this is not about making dating heavier. It's about making your decisions clearer. Sis, you are allowed to enjoy dating. You are allowed to laugh too loudly, order dessert, talk about music, tell funny stories, and appreciate a man with a little swag. Dating with purpose does not mean dating without joy. It means you stop confusing a good time with good character. It means you stop treating chemistry like confirmation. It means you ask enough to understand, listen well enough to hear, and slow down long enough to observe. You are not looking for a flawless man with a perfect answer to every question. You are looking for honesty, direction, fruit, responsibility, and compatibility. And you are giving yourself permission to say, he seems like a good man, but what he is offering is not what I want. That's not rejection. That is discernment. You are also giving yourself permission to say, I do not know yet, but I have a wise reason to learn more. You do not have to manufacture certainty God has not given you. Take the next wise step, then gather the next piece of information, brick by brick, conversation by conversation, date by date. God is not asking you to predict the future. You will not know whether he is the one after one date, but you can discern whether what he is offering deserves another one. So this week, stop interviewing, enjoy getting to know the person, ask natural questions, follow the conversation, listen to his answers, observe his behavior, and after the date, be honest with yourself about what you learned. If this episode helped you, follow dating with purpose on Apple Podcasts, Spotify, YouTube, and share it with the friend who already has her first date questions organized by category and level of urgency. But please let the man finish chewing. And before you go, I want you to answer the question we close with every episode. What would dating with purpose look like for you this week? I'll talk to you next time.