Couple Things with Shawn and Andrew - 311 | ask these questions while dating

Episode Date: May 13, 2026

In this episode, we’re talking all about dating with intention and the questions that actually matter when you’re thinking about a future with someone. Not in a scary interview way 😂 but in a real, honest way that helps you better understand compatibility, values, communication, goals, family, finances, faith, and the everyday things that shape a relationship long term. We’re sharing how to naturally bring up deeper conversations, what we personally think is important to know before committing to someone, and why asking the right questions early can save a lot of confusion later on. Love you guys! Thank you to GoGURT for sponsoring today's episode! Try the GoGURT Simply we talked about in this episode, it’s amazing! https://bit.ly/3HCC0BY Tour tickets, book pre-sale orders and more here! https://thecouragetocommit.com/ You can get a free can of OLIPOP when you buy any 2 cans in-store and they’ll pay you back for one. It works on any flavor, at any retailer. Go to drinkolipop.com/COUPLETHINGS! Get 20% off all IQBAR products, including the Ultimate Sampler Pack, plus free shipping when you text EASTFAM to 64000! Shop the Everyday Cotton collection and all of our favorite bras and underwear at SKIMS.com, and after you place your order, select “podcast” in the survey and choose our show so they know we sent you! Learn more about your ad choices. Visit megaphone.fm/adchoices

What's up, everybody. Welcome back to a couple things. What's Sean and Andrew? Today's podcast is all about intentional conversations or intentional questions that you should be asking, whether it's in dating or in your marriage or in parenting life, things that really swing the pendulum the right direction. That's right. This episode is actually based on a question that a buddy of mine who is currently dating asked me, he's like, hey, what topic should I address with this person I'm dating that

I might want to marry that should be important topics. What questions? How do I go about that? And so I sent him this list that we're going to share. And it's kind of based on this family playbook that we created. And it's all the things that make us, us. And then we kind of backed out. And I created these questions around, man, what does it mean?

What does it mean to be married and to have a family? And what are all the implications of that? So here's to get your guys' insight on this. But first, let's start with some everyday updates. You mean the weekly chaos that's been happening? So I don't know if you guys are familiar with this term, but there is a term called Maysember. Do you know what this is, Andrew? You briefly told me about it, yeah.

I was briefed on it by a mom probably two years ago. And I think this is my first year where I'm really hitting it. And it's where all the chaos of, like, kids' activities and sports and T-ball games and softball games. And then parent-teacher conferences and teacher appreciations and end-of-the-year parties. and it's where everything in spring kind of collides. And moms were not just Santa in December, but we're May December had of tricks where we have to do everything for everybody.

We have been having a blast out. We had our fair share of T-ball games, which is hysterical if you ever see us coming. We have to pack up an entire car's worth of stuff. That's right. All the gear, all the snacks, all the snacks for the teammates, the coolers, the lawn chairs, everything.

And then we basically usually finish a t-ball game and we go sprinting to a softball game. Yep. Which is never in the same location. Yep. And then from there, it's usually to a birthday party. It literally feels like the calendar is impossible at the moment. But it's a lot of fun. It is a lot of fun.

We took Jet to his first motocross track. Sean packed this whole cooler full of snacks. He did a great job. Well, actually, I'm confessing I ate a lot of those snacks. I literally packed an entire cooler because at the motocross track, I kind of kind of figured there weren't going to be any, like, concessions because it's out in the middle of nowhere. You were correct. And I was correct.

There was nothing. But between that and the rock climbing and chess and tasty treats and all the stuff after school, the calendar does feel impossible to keep up with. I agree with you. I mean, the afternoons feel jam-packed. The mornings feel rushed. We got to get everyone dressed, got to pack the lunches, get them out the door on time. Since the kids have been in the actual school.

I feel like the days look totally different. And we go straight from school to practice like Sean was saying. So we're eating snacks in the car. We're constantly on the move. It's a lot. Also, a great, huge, wonderful sponsor, Gogert Simply has changed the game for us when it comes to snacks. It's one thing we have been going through nonstop lately is GoGert Simply. It's truly, like, stocked in every fridge, every car, every cooler that we take.

It's something that our kids have probably multiple times a day. Bear has literally been asking for it. You will lay him in his crib every night. And he goes, yogurt? So. And he literally wants a gogert. The kids are grabbing it constantly or we're constantly grabbing it for them. And it's honestly perfect for this season that we're in.

We can throw it in lunch boxes, hand it to them on the way to practice, or just grab one when we're rushing out the door. And I love that gogert simply is made with simpler ingredients. there's no artificial flavors. It has 25% less sugar than the regular goger and a little tip and trick for you guys. If you put it in the freezer, you can actually take it directly from the freezer and eat it like a little ice, icy treat. Really good. Or just throw it in a lunchbox or in a bag. And by the time you eat it, it's going to be thawed to like the perfect temperature.

So good. And there's no colors from artificial sources either. So freezing them has been my favorite way to eat them. and freezing them before practices has been such a win. The kids think it's a treat, honestly, and it keeps them happy when we're bouncing from one activity to the next. And honestly, anything that's mess-free,

which these are, is a huge bonus. Truly, there's no spoons, no bowls. Just grab it and go, which is exactly what life looks like right now and what is needed. That's right.

And we need a lot of help in this phase of life, to be honest with you. We are, we're figuring it out. I feel like we're learning a lot. I mean, it is hilarious. You think you're done with school once you,

you know, graduate high school or college. or college and then boom, you have a kid and it's like, there's so many activities to do. There is. And it's awesome, but we've had to acclimate to including that into our schedule. And it's been hard. So anyway, back to the dating questions. Yes.

You ready for this? I am. Because I think, I think this is something that people get intimidated by. They don't know how to navigate it. They're like, okay, what do we actually talk about? And I want to preface this that not everything should be addressed on the first date that we're going to just share here. Let's like slow roll these questions. Yeah, yeah.

So maybe don't use all these questions on date one, but spread them out between like dates one through 10 maybe? Yeah. Just it should be a learning process. And you'll you'll kind of know when the right time to ask a question is. I don't think the first date you ask like, hey, should we merge our finances? But maybe, you know, before engagement, that's something helpful to talk about. So we have this list here that we'll go through. Please add to it if you're listening.

like, oh, when I miss that one, or actually, you don't need to talk about that, or maybe even if you have timing thoughts. But one thing that comes to mind, that's a really fun thing to talk about. First question is, what family traditions did you all have growing up? That is a really good one. I feel like, wait, do you want me to answer this? No, no, no, no. We're just going to talk.

No. Yes, I know. You don't want to know? Okay. We've already freaking know your answer is to so many of these questions. I will say traditions, we actually didn't talk about until probably pre-marital counseling. Yeah. Which is crazy because we were a couple of years in.

Premarital counselor told us this one. And it's important because you learn the rhythms that people like are raised with. And then you can talk through, oh, I didn't know that was a thing in your family. Do you want to continue that? And then you start like merging lives together and you understand how people operate and why they operate that way. Okay, quick question. Have you ever felt like you're waiting to feel. 100% sure before you make a big decision.

And then months go by and you're still in the exact same place. Because same. That tension is actually what led us to write the book The Courage to Commit. We started realizing that clarity doesn't come before commitment. It comes after you choose something and stay with it long enough to understand it. Which means if you feel stuck in your marriage, your career, parenting, faith, health, whatever, it may not be because you chose wrong. It may be because you haven't gone all in anywhere long enough to build momentum.

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They mean a lot as far as getting this book out into the world. So if you could do that, that'd be huge. And if you don't know what a pre-order is, it just means you order it now and it gets shipped to you the second week of June. That's right. Please do it. Check it out. We started our marriage. It's changed so much, but we started your one marriage.

I wanted to people over all the time. Come over uninvited. Please walk in. And it's 6 a.m. Yes. Come on. Now it's a nightmare to me. Nightmare to me. I was like our houses are safe haven.

Nobody comes in. Yeah. And I don't want to talk to a stranger to put on like the whole, you know, like entertaining type thing. And you know what? It's become an open door policy. Okay. People are welcome. I have legitimately woken up and walked out into our kitchen and there have been people there.

And I'm like, you know what? Welcome. Oh my gosh. There are times where I like, look. I'm like, what is happening right now? We had one neighbor came over and then five minutes later, the next neighbor just stumbled in. I love it. It's pretty fun.

It has become something. Also, you were out of town either day. I had three people over for dinner. What? Didn't invite them. You didn't invite them. They just showed up. And I was like, join us.

But I feel like it's important to talk about because it talks about, okay, what are the, what was your home life like growing up? Was it an open door policy? Or was it like, no, nobody steps foot in? And then you start to understand different kind of breadcrumbs of, how that person grew up, and that was just a source of a lot of our conflict. The sixth bucket is play, adventure, and daily rhythm. Which is a good one.

And the seventh is emotional and relational health. Okay, so we're going to go bucket by bucket and kind of skim through these questions and talk about why they're important. But first one, the vision for your life. I think this one's really important because this is like the overarching, what is it called, 7,000 foot view, 10,000. What do people say? Any foot you want. A couple thousand? 30,000 square feet.

There you. Not square feet. Just 30,000 foot. But questions like, what do you think makes a life meaningful? Interesting. Is it like career focused? Is it kid focused? Is it adventure focused?

Like, spirit. Like, yeah, it just can be insightful. Also, these are just great questions because when you should, they're phenomenal questions. They're, they're conversational. Something that Andrew and I believe in very strongly, okay? So if you're dating, hear us out. If you're on a date, right, with a new person. And in your mind, in your mind, you have painted these black and white lines of if they are, I don't know, let's say politics because that's just a controversial one, right?

If they believe in X, Y, and Z that puts them in this bucket of politics, there's no way this will ever work. Done. Let's pack up. Let's get out of here. Not even worth my time. I think a lot of these questions, rather than asking direct questions like that, these show you the actual foundation of a human. The heart behind it, yeah.

And then when you start finding out, oh, I didn't know they voted for a different person than myself. It gives you more context to be curious and not judgmental, Ted Lassau. And it honestly might give you reason to say, actually, I don't think I care about that. anymore. Not about who you vote for, whatever, but about the why. I think it can be very shocking. Anyways, that's my little rant. More questions for the visual life is like, do you feel more drawn to comfort, significance, adventurous, stability, impact? Where do you find, yeah, your security in life? Yeah. Another question is, what do you want people to say about you at your funeral? I actually asked someone really close to me is dating and we sat down and I just asked, and I just asked, and

hour worth of questions because I'm highly invested in this in this person who's close to me and I want them to date well. So I'm trying to understand this person and I asked the question, how would your friends describe you? And then also how would you describe your friends? And I feel like that's insightful because one, if that person doesn't have friends, okay, let's talk about that. Is that because there's unhealthy patterns in that individual or, you know, what does that what does that tell me about that person. And then you can also start to understand, okay, if you're the average of the five people you spend the most time with, and they're describing the friends like this, they're kind of adopt some of those things. Another one, this is kind of on the pessimistic side, but I think it's

eye-opening. What would feel like a wasted life to you? So sometimes people would say if I didn't travel the world or get to see other cultures or some people would bring it back to money, it's just eye opening to see the direction of people's heart gets pulled. Also, this is great cheat sheets. Like, if you are dating and you're uncomfortable with asking questions, put it on, like, a little card. And then make fun of it. Like, if you don't like a question or it's uncomfortable, you could be like, oh, this one's

from Andrew East. He's like this goon. And he put together this list. What a dummy. Yeah. You know, just make fun of me. All right. Can we talk about something for a second?

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Okay, so the second bucket, faith and worldview. By the way, you might be using different terms too, like just trying to understand the intention behind the question or the motivation. But the faith and worldview is, are you building life on the same foundation? Back to Sean's like politic discussion, you shouldn't ask, are you Democrat or Republican? Or how do you feel about this specific topic from the beginning? Yeah. Maybe that comes later on. But like, these questions will, will give you insight into their worldview.

So I would just kind of understand, like, what do you believe God is asking your life to be about? That would be tough for like, honestly, a younger person to answer. Well, and you can start by always asking, like, how central is faith in your everyday decisions? Just asking, rather than, like, outwardly saying, are you religious? You could say, like, is faith? Yeah. A part of your life? If it is, how do you make big decisions?

What role does, like, prayer or church or scripture play in your life? Yeah. It'll give you an idea of how they handle that. When life gets hard, how do you? cope? Yeah. And so a question like that, you're thinking, okay, how do they, maybe what they say is what they hope they do to cope. And then you're able to proceed from there and, and watch and observe how they actually cope. And then there's like interesting information kind of that you're gathering there. Some people are like, let me distract myself away from it. Let me not talk about it.

I don't want to get sappy and sentimental. Some people get really emotionally distraught. And it's like more heightened in that sense and they're very free with that. Some people get confused and coping. Some people turn into substances or yada yada. So there's just kind of different insight there. But yeah, the third bucket is family and children. So questions like, what did you love most about your family growing up? What would you do differently? That's always very eye-opening. It can show pain points, things that might. have triggers to them or trauma or just differences of beliefs even yeah uh understanding what do your parents do for work can be super insightful just in understanding someone's ambition it's

like oh my dad bill houses both of our dad's bill houses one that was a really fun oh my gosh show to mine and what time what do you do all he did cabinets or my dad was a general contractor and And then it's like, I don't know, it can be fun to maybe there's overlapping community and like mutual friends that come from that. But it also, you know, there's certain things of like, oh, my dad, he was a professional athlete. Okay, so he was on the road. He was a baseball player. He was never home because he was playing 160 games a year or whatever it is. There's just little bits of information that come as a result of that.

Also, I love this one. Ask about what their dream home looks like. Do you dream of building a home someday? I think it's eye-opening to see what people's ambition to work towards or not is. But also both the physical home, like the space itself and the emotional home. Yeah. We used to sit around the dinner table.

Home to me means the dinner table conversations. Or the fireplace games that we used to play. And then asking about someone's grandparents, How involved do you hope grandparents and extended family are in your life? And some people have that infrastructure. Some people don't. It's good to know. Money, work, and lifestyle is bucket number four.

There's a lot of questions here. I think this is a really important one. But like, what role does money play in your sense of security? Are you naturally a spender, saver, giver, investor? What does enough look like to you? That's a question that we have asked each other. Many times. Many times and it's been interesting.

And all these questions will evolve. You can ask these again, you know, a couple years down the road and it doesn't have to be accurate. But showing where you are and your state of mind and everything is really eye-opening. One question I think is super important is just how ambitious are you professionally? You probably heard us talk about that on a podcast interviews we do. It's just like this idea of ambition. I think some people get so wrapped up and building. that like if I'm all for ambition I'm all for it but it can be all consuming well so just

understanding like if someone's like I'm going to build a billion dollar company just the way they talk about their work some people use it as their identity some people use it as support like how can I just provide for my family you get insight instead of question you get insight we have opinions on what is in our phase of life, not things we value. But someone might be totally fine at that, right? Oh, 100%. Yeah, yeah.

There's no right or wrong answer to any of these. It just helps you learn about a person. Correct. This episode is brought to you by IQ Joe mushroom coffee from IQ Bar. It's delicious low sugar, brain, and body fuel to help you win your day. Okay. We have talked about this before, but mornings around our house are chaotic between getting kids ready, workouts, work calls, all the things.

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And right now, IQ Bar is offering our special podcast listeners 20% off all IQ Bar products, including the Ultimate Sampler Pack, plus free shipping. To get your 20% off, text EastFam to 64,000. Again, text EastFam to 64,000. That's EastFam to 64,000 message and data rates may apply C terms for details. One, last one on this bucket that I think is super important is, where do you give money to now?

One, is this person thinking about that and generosity and serving, which I think is super important. We just did a whole podcast. We were interviewed about philanthropy, not that we're like, you know, leaders. in that area, but it's like an approach to life, I think, that is insightful, but also when you hear about a cause that someone gives to frequently, you kind of understand the wiring of their heart and the operating system of like, oh, man, that person really cares for the underprivileged people, like kids or adults who are struggling in whatever way. It's like, usually when you give, that's like a soft spot for your heart, which is good enough.

Next bucket of community and hospitality is something we already talked about, but ask your potential significant other, do you like having people in your home often? Do you like hosting? Do you like going to parties? Are you introverted, extroverted? Do you, is that fill your cup or drain you? Also, similar to what Andrew is saying, ask about their best friends. How would their friends describe them? How would they describe their friends? Yeah. What role does friendships and community play in their life or their ideal life? yeah do you have any mentors would be another one um and beside your parents who have been the most influential people in your life so like coaches or teachers like that's a beautiful conversation um that i love asking six bucket uh play adventure and daily rhythm uh do you enjoy life in the same way it's kind of the question that that's getting at and this one's a soft spot for you Really? Are you someone who likes routines or spontaneity? I like both.

With children, spontaneity is a lot harder these days. Yes. But I was very spontaneous when we dated. Yes. I would go at the drop of a hat. The drop of a hat anywhere. Some other ones, what kinds of adventures make you feel alive? How do you like to spend Saturdays?

Do you enjoy trying new things or sticking with what's familiar? By the way, the adventure thing, maybe these questions are more insightful to who I am, to be Probably. But like, I would hear some of those questions to adventures and think, you know, we, we're like pretty extreme adrenaline on junkies. So it's like, oh my gosh, I love skydiving. Just like, I've done it a dozen times and I just can't get enough. Some people might think adventure is like, oh my gosh, I went to Trader Joe's the other day and I tried three different types of. And then you're like, okay, now I have.

We're on different. Now I have a framework of like adventure. And what, what are you like a rule follower? I don't know. It's just, yeah, insightful. Last bucket, emotional and relational health. These are important. Sometimes a lot harder to answer because it takes a lot of self-reflecting and self-awareness.

But things like, how do you tend to handle disappointment? How did your parents argue? Did they argue? What does conflict usually look like for you? That was super helpful for us. Yeah. Um, actually one thing I think about all the time, Sean, is you come to me like when Drew was a baby. So like six years ago and saying, hey, one thing I want to practice is having conflict in front of our kids.

Yeah. Because one, I think it makes it hopefully a healthier conflict because you're like, my kid's watching. But two, it teaches a kid like, okay, I'm feeling, like when they're at school and they're feeling frustrated with some other kid in their class, it's like, oh, I know. that we can handle this conflict without having to hurt each other. And we can get through it. Yeah. I think it's so beneficial for people to see that they can get through conflict and still be okay. Yeah.

I agree with that. Some of these questions are hard to answer and you won't know until you see patterns develop over a long period, maybe even years, a long period of time. But like, what makes you shut down? so one thing like if i tell sean to do something like we're we're gonna go to this thing and we're doing it tomorrow sean just like mentally checks out is not not into our noise on a directive noise makes me shut down noise does yes um asking what is your love language i think is good and then you know maybe that leads to something like oh what's your enneagram number people love talking about that sometimes or what's your Myers-Briggs thing and oh baby we got the two newest flavors of

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That's right, especially in afternoons. I feel like we always hit that point where we want a little pick-me-up or something sweet. And olipop has been our go-to. And I also love that it supports digestive health and has way less sugar than traditional soda, like the raspberry sherbet. It has only 30 calories, 6 grams of fiber and 2 grams of sugar, which is wild considering how good it tastes. That's right. And the blackberry vanilla has 9 grams of fiber. Apparently 95% of Americans don't get an of fiber, which honestly checks out because I definitely wasn't thinking about fiber before I was drinking out. No, same. And I just wanted something that felt a little better for me without giving

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Dotop is available nationwide in the soda aisle and chilled beverage section at places like Target and Walmart. I don't know. It's kind of a fun exercise, but I'm curious, John, which of these buckets do you feel like we didn't talk about enough in our dating process? finances yeah yeah I think it was a little bit of a taboo topic for us or one we didn't feel like it was necessary to talk about what would you say um I didn't understand the complex yeah I mean regardless inevitable I think in any of these seven buckets there's going to be complications

that you don't find out about until later but like your situation since you started professional gymnastics age 12 your situation with money was just more complicated and there were people who hurt you and things that triggered you that like I just didn't know

so yeah but but again would you say though probably community and hospitality we didn't really talk about I think I just I think I just plugged you in to

the existing kind of thing that I was doing, which I think we talked most about vision for life and least about kind of like the stylistic differences, which it worked out fine. Yeah. It's great. Like I don't think we should have hammered conversations about money because then you start thinking, oh, this person cares so much about money, which is not how I operate. Yeah. But, but yeah, I'm curious what you all think.

Was that a healthy balance? balanced list of questions was helpful. Did we miss anything? I loved dating Sean. I did. I loved dating you. It was just really fun. And there's like one thing, we have not really talked about this much, but I learned within five minutes of being with Sean that all people usually ever ask her about is gymnastics and dancing with the stars and the Olympics.

like that's all she would talk about. So in my mind, I was like, I could probably just find out most of that, that information by, I don't know, Googling it or something. Let me see who she is. Let me actually see the other parts about who Sean is. And just to kind of, to kind of like see what made you smile. My freaking favorite. Let me see it.

It's my favorite thing. It's like, that was what really drew me towards you. and to hear about your friends and the nonsense stories that you all got into. And like, you know, Chicago, New Year's Eve is the first story that comes into mine there. Oh my gosh. I forgot about that. Yeah. My rebellious years, guys.

Dating is really fun. And it's also responsibility. And there's also a purpose to it is how I approached it. I'm not prescribing this to anyone. but in my mind I was like I have to find out I'm on a mission to find out if Sean is a girl

that I could marry and you were I didn't know we're going to talk about our dating life but one memory that sticks out for me I had trust issues I was so skeptical and just like to a certain extent like a cynic

in the dating process. I thought everybody had motives. And so for me, it was all about observing and listening and like trying to take in the whole picture. And there was something so

moving about how everybody around you looked at you, talked about you, helped you. It was infectious and it was so genuine. Everybody you associated with early, like, I'm talking like early, early dating within the first few days of dating. To see your community was unlike anything I'd

ever seen before. We might have shared this in the dating series. With Sean and I was first day, I pick her from the airport and a Ford Flex, which looks like a refrigerator on wheels. Oh, sorry, no, no, no. I was correct. You borrowed your teammates truck. Because I was driving a Ford Flex and I was like I got to come up with something different. So I borrowed my buddies like 1995 Chevy. It was red. I think it was like Burgundy Red. I think it was a shana went straight to the Vandy baseball game where we didn't have

enough money to buy tickets. So me and my teammates were having a grill out session watching the game on the top of this parking deck where you can see part of the field. And I introduced her to a bunch of my friends and then our second date. And everybody was so kind. Oh my gosh. I have and I had a wonderful group of friends. Our second day was like me introducing to my family.

Yeah. Honestly, the way I operate is like I am no greater or less than these people who. You had not operated like that until then, though. As far as like you didn't take your previous girlfriends to meet your parents day two. Correct. But you and I literally approached our relationship that time with like, I'm not in this to just date. Yeah.

I want to see if this will work or not. So balls to the ball, baby. Yeah. And I'm glad we did that way. It's been really fun to ride. And I feel like we're still dating and it's still fun to like continue to get to know each other in different ways and ask. Honestly, questions that are not too dissimilar from this and just different contexts of

life in different ways. So curious to hear you guys' thoughts, but thank you for watching and to see you next time. I'm Andrew. I'm Sean. Till next time.