I was the king of dating with regrets. I ended up engaged to the same woman three times—and unengaged three times. I had two kids with two different women before I turned 21, and I left a trail of broken hearts in the midst of self medicating my own.
I dated carelessly because I didn’t have a foundation for how to date well, and it left me with a lot of wounds.
How do you feel when you hear the word dating? If a mix of emotions like fear, anxiety, hurt, and regret swell up in you, then chances are you’ve felt the sting I have. Through all the mistakes, I’ve had a few big learnings that I’m hoping will encourage you to make better dating decisions in your life.
You don’t have to believe in God to go with me on this, but I do, and the way he sets up dating and marriage is actually really helpful. It protects us from unnecessary pain. This might sound harsh, but it helped me to learn that in God’s eyes, he doesn’t recognize the relationship you might have between your girlfriend or boyfriend. The relationship steps mentioned in the Bible are single, engaged, and married. The first step to dating without regrets is understanding why you want to date in the first place.
I used to enter into relationships and treat them like marriages. Not with the “forever commitment” part, of course—more like a temporary marriage. Now, looking back, no wonder it hurt. I would put whoever I was dating above my responsibilities, friends, and family, and I would constantly make excuses for poor behavior in the relationship. I thought prioritizing the relationship above everything else was healthy when, in fact, it was just the opposite.
One of my biggest regrets came after spending my post-college savings to drive across the country to start my career and life in Los Angeles. A month later, I got a phone call from my ex-fiancée (who was dating someone else at the time, but I didn’t care) saying she wanted to get back together. The next day I had all my stuff packed and was driving 30 hours across the country again to save the relationship. I didn’t use conventional wisdom. I just did what I thought would save the relationship, and once again, it ended as a big dating regret.
I had my reasons, and some seemed honorable at the time. I hated giving up on people, so I would fight for them until the end—no matter what. It took me talking with wiser people to realize that dating was never meant to be a long period of time where two people cleave to each other like spouses. If you choose to treat your girlfriend, boyfriend, or even your fiancée like a spouse, it doesn’t allow for your relationship to go through the true evaluation process that dating is intended to be.
When my (now) ex-fiancée called off our wedding for the third time, I knew I needed a change. That night I chose to stop getting in one terrible relationship after another then trying to pick up the broken pieces. I decided to break the cycle by not dating for a full year.
That’s when I learned I was a misinformed guy who had picked up some bad dating habits, but I was willing to change. Just to make it easy to remember, I’m going to call the three biggest changes the three C’s. When I started applying them, I was able to honor the women I’ve gone on dates with and also walk away from them without feeling any regrets or hurting them. Those three C’s are dating with confidence, clarity, and celibacy. Please don’t stop reading because I just said that third one. Go with me for a bit.
In my experience, relationships stall out because someone isn’t confident enough to either end the relationship or take it to the next level. Rejection is scary, but if you don’t take the risk of asking out the person you like, then you will never know how they feel about you. They might say no, but trust me, it is a better feeling to ask someone out and have them say no than to keep wondering what might happen. People want to go on dates and be asked out. Even if they say no, by being confident enough to ask them out, you blessed them in a way that encourages them to see that someone noticed them. Be confident in who you are and then let that confidence reflect how you act in a relationship from beginning to end. If you can learn to do that, then you won’t make poor decisions like staying too long in a relationship or missing your opportunity because you never asked someone out.
Dating with clarity is the best way to honor someone you are currently dating. Nothing is more awkward than spending time with someone and not knowing if it’s a date or not. This usually happens when someone asks you to get drinks, coffee, or (the worst) “to hang out sometime,” and you’re left trying to guess if they’re interested or not. If you’re a woman and a guy asks you to coffee or dinner alone, be bold enough to ask his intentions. If you’re a guy, be bold enough to tell a woman your intentions before the waiter asks, “Is the bill on one check or two?” You know it’s coming. Speak up before that awkward moment, for the love.
This is why dating is full of messed up trends like ghosting and breadcrumbing that leave people confused about how the other person feels. You’d rather someone tell you the truth—even when it’s difficult—so think about their feelings and tell them the truth as well. If you don’t tell them where you stand in the relationship, then that’s not honest; it’s passive. If you can’t say where you are, notice it as a red flag and either push through or get out so you don’t waste each other’s time. People say they want someone who plays hard-to-get or who is mysterious, but oftentimes those are the relationships that don’t last because you can’t build anything on games and confusion. But you can build a joyful, God-honoring relationship through healthy communication and clarity about the direction the relationship is heading.
Now trust me on this one: Dating celibately is the single most important key to dating without regrets. When I say date celibately, I’m not saying act like you never want to have sex again. I don’t expect you to be a nun or a monk. I’m suggesting that you acknowledge the power of sex, how blinding it can be, and choose to say no to that desire until you have committed fully to someone as your spouse. Whether you believe in God or not, he honors that. It works. If you don’t remember anything else about this article, remember it is always easier to walk away from someone without regrets if you haven’t slept with them. Here’s why:
Every time we have sex with someone, something deep inside us (our spirits) are coming together as one and then tearing apart as soon as we’re done. You know that feeling? The Bible actually warns us about it—not because God is holding out on us, but because he wants to protect us from the heartache it brings. The pain far outweighs and outlasts the momentary pleasure sex provides.
Having sex while dating is like driving while blindfolded. There could be major red flags and dangers about dating someone, but you won’t be able to see them because you’re blinded by how they make you feel during sex. You keep driving unaware of the hazards ahead of you and, eventually, you end up crashing the relationship with regrets that take a long time to recover from. This is how I would describe myself as I drove blinded from LA to Cincinnati unable to recognize the toxic relationship I was trying to save because my mind was too focused on the sex.
Celibacy is usually mocked and seen as something that limits a relationship from growing, but it actually gives freedom in dating. When you own a dog, there are certain modifications you have to add to your house to help keep the dog safe. You build a fence around your yard because you want them to experience the freedom of the yard without the dangers of running away. Celibacy is like a fence to experience the joy and intimacy of dating without our hearts running away from God (and getting torn apart). He doesn’t want us to experience dating regrets, and he doesn’t want our bodies harmed in any way—because he’s a good father. Celibacy helps us navigate dating free of shame and guilt. Also, let’s be honest, not having sex is a great motivator to help push the relationship forward towards marriage instead of staying stuck in a dating period that never ends, or to end it quickly if it’s not going anywhere.
Dating can be hard and confusing, but in my experience, if you date with the three C’s, you will position yourself to find the results you want instead of the regrets you don’t.
Process, journal or discuss the themes of this article - here's a few questions to get the ball rolling...
If you had to sum up the root of your dating regrets, what’s the source?
Which C is the easiest for you? Which one is the hardest?
What’s one thing you can do this week to have a healthier dating life? Tell a friend and do it.
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