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Love, Dates & Heartbreaks Part 5 | "Learning From Past Relationship Mistakes"

When it comes to relationships, how do we make sure we’re learning from our past mistakes instead of repeating them?

  1. Do you agree that experience alone doesn’t make you wiser? Why or why not?   
  2. Have you ever bought into the Know-Better Myth: “If I know better, I’ll do better.” Explain.
  3. How could viewing time as your friend improve your relationship or dating life?
  4. Have you ever assumed that sex would solve a conflict or fix a dissatisfying relationship? Explain.
  5. The apostle Paul encouraged Christians to “be transformed by the renewing of your minds.” Which area of your life could benefit from removing the old to make way for the new? Explain.
  6. If you’re dating, what would be the benefits of taking a year off? What’s your biggest reservation about doing so?

NOTE: The following content is a raw transcript and has not been edited for grammar, punctuation, or word usage.

So today, we are in Part Five of our series Love, Dates & Heartbreaks. And if you haven’t been with us, this is a series for anybody who is in love, trying to stay in love, hoping to fall in love, dating, dating again, thinking about dating, thinking about dating again, scared to death to date again because you’ve heard how complicated it is. And we talked about that last time. Also, the reason I love this series is because I get to talk about something that breaks my heart and everybody should know it breaks their heart and you should pay attention to what breaks your heart. That might be some direction for your life. But one of the things that breaks my heart is watching people make relationship decisions that actually undermine their relationships, either the relationship they’re in now, or a relationship they don’t know about in the future that they’re undermining before they even get there because of decisions that they’ve made.

Today we’re gonna talk about avoiding groundhog date, avoiding groundhog date. And of course, groundhog date means this last, that last one was kinda like the one before and this one’s feeling like the one that came even before that.

We’re gonna talk a little bit for a few minutes about how to break the relationship habits that are breaking you. How to break the relationship habits that are breaking you. How to break those relationship habits that cause you to feel like, “Hey, this is starting to feel like the last relationship.” Or another way of saying it is how to date in a different direction because as you’ve heard me say before and you’ll hear me say again, your direction, not your intention, determines your destination. Your direction, not your intention, determines your destination.

The challenge, of course is, as in any area of life, but maybe especially with relationships, it’s difficult to change directions. And part of the problem is, part of the problem is we learn from our mistakes in the arenas or the areas of life that matter least. Now, I could talk a long time about this, but I’ll just kinda leave this with you. You can talk about it over lunch or dinner because there’s so much truth here. We learn from our mistakes in the areas that matter least, and we repeat our mistakes in the areas that matter most, which is so strange. So, you’ve finally figured out Twitter, you’ve finally figured out Instagram, you’ve finally figured out social media, you made a whole bunch of mistake, it’s like, “Wait, so everybody can see this?” “Yes, Mom, everyone can see that [laughter], okay.” So you figured that out.

It’s amazing, we learn from our mistakes in the areas that matter least, but we have a tendency to repeat our mistakes in the arenas of life that matter most, especially when it comes to relationships. Now, why is that? Well, I think there’s several reasons. It’s these myths that we’ve talked about, these relational myths that are in the background of our thinking. Any time you have an unexamined assumption in any area of life, an unexamined assumption is a dangerous thing because an unexamined assumption will inform your decisions and inform the way you think. But if you’re not aware of the assumption that’s driving your thinking, you can come up with all kinds of crazy conclusions about stuff. And when it comes to relationships, it’s amazing the unexamined assumptions we carry into adulthood oftentimes from childhood. So we’ve talked about some myth. There’s the Experience Myth. The reason we repeat our mistakes relationally is the Experience Myth. Experience will make me wiser. That’s a myth.

Experience will make you older. That’s what experience does. [laughter] Experience doesn’t necessarily make you wiser, it makes you older. Experience does not guarantee that next time is gonna be any better than last time. Evaluated experience is what makes us better. And you know what’s so interesting? When it comes to relationships, we do not evaluate our experience, and I’ll tell you why, because instead of evaluating this way, we evaluate that way. Well, of course, it didn’t work out, he’s an idiot.


Well, of course, it didn’t work out, she’s crazy. So instead of evaluating our relational experience, we just blame and then there’s the Know-Better Myth, this is huge. The Know Better Myth is, “Since I know better, I’ll do better.” That’s just not true.

We think that if we know the difference between right and wrong, we will probably do what’s right and if we know the difference between right and wrong, we automatically have the self-control and we automatically have the discipline to do the right thing.” But that’s not true.

Since I know better, I automatically have the ability to do better. It’s a myth, because know better does not equal do better. And here’s the other myth that just causes us to lose our mind relationally, it’s the Time Myth. The Time Myth is this, especially if you’re like 25 I mean you’re practically ancient if you’re 25, that time is against me, right? I mean, I’m not getting any younger, which is true, I’m not getting any younger. Everybody else my age, all my friends, if I have to be in another wedding, I’m gonna scream if I hear about another friend getting engaged. I mean, all my friends, all my friends are divorced but everybody seems to be finding somebody. I’m not getting any younger.”

So, the Time Myth is that time is against me. But I have some friends, Sandra and I have some friends who are a couple and it’s a second marriage for him, it’s a first marriage for her. And they spend a lot of time with couples that are moving into that season of life where either it’s a second marriage for both or a second marriage for one, and they love spending time with people moving into a second marriage because they navigated the complexity of all that, and on the front end it just seemed so simple, we’ll just blend our families and blend our time. And you know what they told me, they said., “Andy, here’s what we try to convince individuals and couples of. Here’s the most difficult thing to convince couples of and individuals moving quickly toward another marriage. The most difficult thing to convince them of is this: Time is your friend.” Time is your friend. If you want to date and you want to live and you want to romance in a different direction, you need a break and time is actually your friend.

You need a break to regain balance. You need a break to gain perspective, to gain clarity, to work on you because here’s the thing: In time, in time, in time you will be able to hear things you can’t hear right now. In time, you’ll be able to see things you can’t see right now. And here’s the one you’re gonna hate me for: In time, you’ll be able to own things you can’t own right now. With time and a break, you’ll be able to recognize your contribution to the problem. With time, you may be able to recognize and own your slice of the pie, but without time, without a break, you know what you’ll do? You’ll do what we all do. You’ll just blame and you can’t blame your way into a better future. In fact, blame has an insidious way of allowing us to smuggle our issues into our own future. Smuggle our issues into this next relationship.

If you just blame the other person, you have set yourself up to think about it, to smuggle your stuff into your own future instead of leaving it behind. Smuggle your relationship’s issues into the next relationship. So blame actually sets us up for rents and repeat, right? Welcome to groundhog date.

So today, I wanna just give you the first step to dating and doing a relationship in a different direction. And the reason I just wanna give you the first step is number one, we don’t have much time but number two, if you get the first one right, the rest take care of themselves because you’re smart, you’re smart. And once you begin to unearth some of these assumptions you’ve been carrying around, and you look at him and you go, “Well, that’s ridiculous. I’ve been making decisions based on this and this just isn’t true.” Then you’re on your way.

So, to set us up for where we’re going, none of this is original with me, I actually learned this start off change direction thing principle from the Apostle Paul. The Apostle Paul was a Pharisee in the first century, then he became a Jesus follower, and then he decided to do a crazy thing, he decided to take the message of Jesus to the non-Jewish Gentile world.

And so he shows up in this Gentile, pagan, idol-worshipping, slave-owning, might-makes right culture, and he’s talking about the fact that God sent a Messiah, a Jewish Messiah, with this strange message that we’re to love each other, and everybody has dignity, and women have rights, and children have rights, and slaves have rights, and everybody’s equal in the eyes of God and made in the image of God, and everybody’s supposed to love each other, and God punctuated this message by raising someone from the dead. It’s amazing anybody took him seriously, but they did. And so the church began in the non-Jewish world around the Mediterranean basin.

And he had to confront so many assumptions. And yet, somehow he was able to gain traction with this extraordinary message that there is a single God who has done something in the world for the world, and it will be characterized by giving value, equal value to the people around us. And so to help them reshape their thinking and really embrace a completely different worldview, which may be your resistance to Christianity, because the Christian worldview in your world if you don’t line up. I totally get that. The Apostle Paul totally got that. So it’s a good thing, perhaps that you hear a message like this to know you’re not alone and God isn’t angry. God would love for you to maybe change your thinking to see the world in a different way.

So the Apostle Paul wrote all these letters to this primarily Hellenistic culture, Greek-speaking culture and in one of those letters he wrote to Christians living in Rome, during the time of Nero, not a great place to be. And in that particular document, it’s not even a letter, it’s just this huge, amazing document we call the Book of Romans, he gives what he gave in other instances as this first step to beginning to think differently about everything. But today we’re gonna apply it specifically to relationships. And here’s how he began, Romans chapter 12, so we’re like way into this big document. Here’s what he wrote, he said, “Therefore, I urge you,” and the reason he has to urge us is because there’s gonna be resistance. “I urge you,” you’re not really gonna wanna go along with this, “I urge you,” even though this seems a little bit strange.

“I urge you brothers and sisters, in view of God’s mercy,” which means basically a lot of everything God has done for you, and what has God done for you? Well, He took 11 chapters to tell us. So you can go back and read that on your own, but basically, here’s what he’s saying,      in light of everything that God’s done for you, in light of God’s mercy, he says, “Here’s what I want you to do.” These are my words, not his. “I want you,” it’s a big ask, that’s why he’s urging. “I want you to write a blank check with your life and offer it to your heavenly Father. Not in order to get something, in light of what He’s already given you.”

“Therefore I urge you brothers and sisters, in view of God’s mercy to present yourself,” or to offer your bodies, “as a living sacrifice, holy and pleasing to God. This is your true and proper worship.” Now, when we see the word sacrifice, nothing comes to mind for us was, you don’t make sacrifices, but everybody in this culture had made sacrifices and seen sacrifices made, and so he’s using some interesting imagery that possibly caused those who read this for the first time to chuckle because he’s saying, “Here’s what I want you to do. I want you to climb up on the altar as a living sacrifice and offer all of yourself to God, not in order to get something from God like the pagans were constantly trying to do with their sacrifices, but in light of what God has already done for you.” And then he uses a very interesting word, a word that’s so cool that it takes two English words to translate the one English word.

He said, “And this act of offering yourself to God is the most logical thing you could possibly do.” The Greek word that’s translated true and proper is the Greek word from where we get the English word logic or logical. He says offering yourself to God, I know it sounds like a big risk, I know it sounds like a big sacrifice, I know it sounds like a big Say No to yourself but Paul says, “I’m telling you, this is the most logical, thoughtful, reasonable thing you can do because God is for you and God knows what’s best for you. In fact, refusing to is the most irrational, illogical thing you could do.”

Then he goes on, he says, “And here’s the deal. Don’t be conformed. I don’t want you to continue to be conformed to the pattern of this world.” Literally, the verse means this: Do not be conformed according to a pattern or a mold. Don’t form yourself or allow yourself to be formed. In other words, don’t be this guy. Okay? [laughter] Don’t be this… I don’t think there are gingerbread women, I’m not seeing a gingerbread woman [laughter] so we’ll just go with gingerbread man. Sorry, ladies. Don’t be this guy, right? If you be this guy, if you be this woman you end up like everybody else. He says, “I don’t want you to be conformed. I want you… ” Look what he says, he says, “Don’t be conformed,” but you can actually be transformed or literally in the Greek, it’s allow yourself, allow yourself to be transformed.

So, do you wanna be a conformer like gingerbread man? Here’s what it sounds like in our culture: Guys are all the same. Guys are all the same. Guys are all the same. Guys are all the same. Guys are all the same. Women only want a ring. [laughter] Women only want a ring. Women only want a ring. Women only want a ring. It’s all the same, right? He says, “Look, you don’t have to live your life that way. There’s a different way forward in every arena of life, especially relationships.” So the question is this: Do you wanna be a conformer or would you rather be a transformer?


That’s what I’m talking about, right?


Now unfortunately, this is the evil transformer, but I thought it was cool so we brought it out, alright? [laughter] This just happens. This happens with no effort at all. He says don’t be a conformer, don’t be conformed, be transformed, and then maybe if you’re new to the Bible and new to Christianity, you don’t know this.

As in every instance, the Apostle Paul actually tells us how to do it. This isn’t, I just go out there and figure it out for yourself, even though all you need is a little bit of a head start, all you need is that first step and you can figure this out for yourself. He says don’t be conformed but be transformed. How Paul? He says, “Let me tell you how. By the renewing of your mind. By the renewing.” Not by a prayer you pray, not by a commitment you make, not by a promise you make God. This is not a moment in time, this is a process. To renew your mind is to restore, it’s to change, it’s to re-do, it’s to pre-program, it’s like repainting a car, when you repaint a car, what do you have to do? You gotta sand off all the old and you put on the new. It’s a two-step process. Re-finishing furniture, sand off the old finish, put on the new. Unless you use chalk paint, which is a cool thing but it messes up my illustration.

So, you gotta take off the old, put on the new; take off the old, put on the new; wax off, wax on; wax on, wax off. Okay, whatever generation you’re from. Yeah, you gotta take something off before you put something new on. So what happens? I mean, you know, this. What happens when you put on the new before you take off the old? The new peels off. And this is why so many people sincerely make promises to themselves, they sincerely make promises to God, they sincerely make promises to a higher power, they make all kinds of promises and they are as sincere as they can possibly be. And the next time it’s just like the last time, it just doesn’t stick, it just peels off. And the Apostle Paul says, “Look, I urge you, I urge you, I urge you in light of all God has done for you, would you hit pause and would you present yourself to him a living sacrifice? Would you basically write a blank check with your life and say, “God, okay, I have screwed this up so many times or I get it right some of the time, but I am so tired of calling my own shots and so I’m gonna surrender myself to you and relationally, I’m gonna hit the pause button and I’m gonna go through the long maybe difficult process of renewing my mind so I am no longer conformed so that I can be transformed.”

But the trick is, the difficulty is, and the thing that we don’t like about this is that renewal takes time, which brings us back to this: Time is your friend.

Just to use some church-y terminology, if you will invite Jesus to be the Lord or the boss or the king of your life, and if you will spend some time allowing God to renew your mind, here’s the result, then… Then as a consequence as a result, then you will be able to do something that in the past you struggled perhaps to do, then you will be able to test and approve, literally, then you will be able to determine and discern.

Then you will be able to figure out. Figure out what? What God’s will is. This is so powerful. A renewed mind, a renewed mind is able to make sense of God’s will. See, part of the problem is this: Until we can see as he sees, we’re not inclined to do as He says. When you renew your mind, what made absolutely no sense before becomes a, “Oh, yeah.” Human nature is, we are far, we are far more inclined to do what makes sense than what we’re merely told to do, right? And here’s the beauty of following Jesus, and here’s the beauty of the New Testament, and here’s the beauty of what the Apostle Paul taught, the Apostle Paul says, “Look, your heavenly Father wants you to understand. This isn’t simply do as I say and you’ll maybe someday one day you’ll figure it out.”

As you spend time renewing your mind, there will be moment after moment after moment of, “Oh, oh, oh, I can see what I couldn’t see. Wow! It’s so much easier for me to hear what I couldn’t hear. And wow! I’m beginning to feel the freedom to take responsibility for things I was never able to take responsibility for before.” Because a renewed mind recognizes God’s will for what it is and the Apostle Paul tells us what it is. His good, it’s good because it’s good for you. His pleasing, which means you know what, in the end it’s actually gratifying. The will of God on the back-end is I’m so glad I did this, I’m so glad I surrendered, I’m so glad I obeyed. And his perfect will and the little Greek word here actually refers to maturity that over time, you will become more mature because you’ll see in a way you’ve never seen before, you’ll think in a way you’ve never thought before because as we’ve already learned, right? Regret and resolve, they’re just not enough. If regret and resolve were enough, we would never repeat our mistakes. Regret and resolve just aren’t enough.

I’m sorry and I’ll do better rarely makes us any better because if you think the way you’ve always thought, come on, you’re just gonna do the way you’ve always done. You’re always gonna do what you’ve always done. And the result, boom! Groundhog date, groundhog marriage, groundhog relationship.

Think about it this way, we’ll move on, everything you’ve ever done relationally, everything you’ve ever done relationally made perfect sense to you. You didn’t do things that didn’t make sense. Every time you called you lied, you got in, you got out, you left, you moved in, you moved out, whatever it was, you told her that… Every decision you’ve made relationally, it made perfect sense to you, but if it doesn’t work, if it’s not working, maybe there’s more, maybe you need a break. Maybe you need to clear your head, maybe you need to change the way you think, maybe you need to renew your mind because a transformed mind results in a transformed life. And transformation takes time, and it takes focus, it takes time, it takes focus, and it takes attention. It might take a different rhythm, it might require some different friends, it might require you to make a difficult decision, but in the end you will be able to discern and understand God’s will for you.

And here’s the great thing about renewing your mind: Over time you will begin to let go of some lethal, unexamined assumptions. It will empower you to let go of the ways of thinking that keep you in bondage and keep creating, keep making the history repeat itself relationally; assumptions that deserve for sure, assumptions that deserve to be examined.

Here’s one we’ve talked about: Once I find the right person, everything will be alright. Number two, My situation is unique.

Now, let me just say to those of you who say this, ’cause I love you, I don’t know you but I love you, I care about you. Do you know why we say this? This is how you avoid good advice. If somebody gives you good advice, “I-I-I I know, I know, I know. See, I know, I know, I know, I know, I know, I know. My situation’s unique. It’s not. Listen, your situation is not unique. You are unique, your situation is not. And when you use, “Well, my situation is different.” You’re just avoiding good advice, you need to knock it off. That is a fatal assumption. Here’s the third one. “Well, it may not be right, but it makes me happy and God wants me to be happy.” [laughter] I’ve heard this 10,000 times and I never know whether to hug the person or just throw up. [laughter] I’m torn and I understand, I sound like I can be critical, I’m not. This is a heartbreaking statement, I’ve heard it so many times. “Andy, I know what you’re saying, I know what you’re saying, but you know what, it makes me happy.” Look, if it’s not right, it’s not gonna turn out right. If it’s not right… ”

And besides that, Jesus actually gave us the happy formula. You wanna be happy, Jesus actually told us, in fact it’s his most famous sermon and he opens up with it. Happy are those who… And in part of his happy sermon is Matthew chapter 5, here’s what he says, “Happy are those or blessed are those who hunger and thirst for the right thing because they will be full.” Because here’s what you’ve already learned. Chasing your appetite does not leave you full, does it? It leaves you empty and wanting more. Fulfilling an appetite only strengthens the appetite and it leaves you empty and wanting more and your Father in heaven who loves you, through His Son who paid for your sin says I want you to follow me, and I want us to chase down righteousness and when you chase down righteousness in the end, you will be full. So all these fatal assumptions, all of the stuff that swirls around in the background when you begin to renew your mind, you begin to identify these things and move on.

Here’s the fourth one. Sex will solve it. [laughter] Sex will solve it, right? No. Sex will complicate it, you know that. Sex doesn’t make your life… It just complicates the relationships, it creates obligations, it creates expectations. And what’s the third thing it creates?

Children. [laughter] That’s exactly right. You got it, babies, that’s what sex will do. That’s what it does. So that whole thing of, “Well, once we move in, and once… ” Now, that’s just a lethal assumption and you’ve been through that over and over and over.

So, to borrow Paul’s words, I wanna urge you, in view of God’s mercy in light of all that God has done for you, the parts you know about, the parts that you still haven’t even discovered, would you not just hit pause and just surrender, especially this area of your life to him? Surrender your body, your body as a living sacrifice, this is your true and proper worship, this is the most reasonable thing you’ll ever do. And come on, and don’t keep being conformed, quit being this guy and no longer be conformed to the pattern of this world but be transformed by the renewing of your mind. And if you do, you will be able to recognize God’s will for you. His perfect and perfecting, his pleasing because it’s fulfilling and his maturing will for you.

And specifically, for those of you who are dating and it’s just round and round and the last relationship ended up like the one before and it just seems like you’re, “As soon as I find the right person, as soon as I find the right person, as soon as I… ” You’re just in that treadmill of relationship, here’s what I want you to do. And I’ve been challenging people to do this for years and years and years, over 10 years. Would you be willing to take a year off? Would you be willing to just stop? Would you be willing to take a year off? Specifically, would you go out a year from today? Whenever you’re hearing this or watching this, would you go out a year from today and mark your calendar and say, For a year I’m out, I’m getting out.

And during that year, I’m gonna read and during that year I’m gonna start praying again and during that year, I’m gonna surround myself with some people who think differently about all of this. During that year, I’m gonna move out. During that year, I’m gonna break up. During that year, I’m gonna clear my mind and I don’t care who shows up. I am taking a year and renewing my mind ’cause I don’t wanna spend another season of my life like this guy. If you don’t want the next time to be like the last time, you have to do something different in the meantime. You have to renew your mind, you have to be transformed by the renewing of your mind. And if you take some time to renew your mind, you’ll never, ever, ever regret it. But I have to warn you about one thing if you do this. Two weeks after you make this decision, you’re gonna meet him.


Two weeks after you make this decision, well, there she is. Oh, that’s just perfect. I’m two weeks in and there she is. I wonder, “Hey, listen, can we talk? Okay, would you wait on me for about 50 weeks is all I need you to do. I just need you to wait on me basically a year and I’m… ” And when you see him, and when you see her and when you’re sure, I’m sure they’re the one, you ignore them. You’re not ready for them because you are being transformed by the renewing of your mind. You’re becoming the person that the person you’re looking for is looking for. If you don’t want next time to be like the last time do something different in the meantime. That’s how you prepare to do relationships in a different direction. That’s how you prepare to do marriage in a different direction. That’s how you prepare to date in a different direction. That’s how you prepare to avoid groundhog date.