Lessons From My Exes

lessons-learned-from-exesWhen you are 30 and not married its possible that you have dated quite a few people. You may have had some serious boyfriends, a fiancee, guys you “talked to”, or even just a million first dates. But hopefully when all is said and done, you at least learned something. :)

Because I love you and I want your life to be easy, I am going to share what some of my ex-boyfriends have taught me ;) No names have been used to protect the innocent (and the guilty), but I do link to their facebook pages, so you can avoid the same mistakes I made.
Just kidding.

I like to think that my naivety was because this was my first “real” boyfriend. I was 17, a late bloomer, and I didn’t know this guy from Adam, but his best friend had asked out my best friend, so of course I was going to say yes. I grew up in the church and going to youth group where it was embedded in us to date Christian men and not to be unequally yoked, which I am so thankful for, even though I didn’t always listen. When I saw a Bible next to his bed, I sighed a sigh of relief and checked that off the list. Fast forward 3 weeks later and I head to Peru for a mission trip. Soon after I get back, my best friend gently lets me know that I should probably break up with him, because he cheated on me. He had sex…with 3 girls…while I was on a mission trip. Just let that sink in.

Lesson Learned:
A Bible next to the bed, does not a Christian make. If you go on several dates with someone and faith does not come up or if he says he is a Christian and there is no fruit, then you should realize you may be unequally yoked. Not being on the same page spiritually will always cause strain in a relationship. I guess when we were having that “waiting for sex until marriage talk” I should have realized it was mostly just me talking.


Ahhhh young love… young stupid, love. You remember your first serious boyfriend, right? You were probably glued at the hip, may have even ditched all your friends, and believed that you’d be together forever! And if you were like me, you were dependent on them to do everything right for you to be happy. Ughhh… I was a mess… I am not even sure why he liked me. I was whiny and needy and way too dependent on him. I was not very easy to please and even cried one Christmas, because he made me something instead of buying me the promise ring I wanted. I cried. He made a sweet gesture, by spending tons of hours building something that I had actually mentioned I needed, and what did I do? I cried. Because it wasn’t exactly what I wanted.

Lesson Learned:
Don’t look to another person for your happiness. They will fail you, because they were never designed to fulfill you in that way. Until you are satisfied by your relationship with the Lord first, no other relationship on earth will satisfy!

Have you ever met a guy who had every quality you always wished for, but something just wasn’t right? I did. Each time I learned something new about this guy, I was blown away and typing out his list of positives was giving my hand a cramp. He was the male version of the Proverbs 31 woman, the complete package. So what was the problem? Why wasn’t there a connection?

This question plagued me the whole 2 months we dated… even to the point of going to pray with someone at the church. I could not understand why I did not fall for this guy who was seemingly everything I wanted. I assumed I was sabotaging something and something from my past was blocking my heart or preventing me from opening up. I don’t think it was any of that. I think the truth was just that I knew He wasn’t the right one for me.

The Lesson: It was then that I learned the difference between the “perfect” guy and the “perfect for me” guy! Don’t feel guilty or like there is something wrong with you for not connecting with someone who seems perfect. Forcing something that shouldn’t be, is a sure way to get into a relationship that is doomed to fail.

I have for years had this trio of qualities that I wanted in a guy. Sure I had a longer list of things I hoped for, but these were my non-negotiables… or so I thought. I remember sitting in his car and him trying to convince me to go on a date with him. To which I responded, “I have this trifecta…. of what I want in a guy… Funny, Good looking (to me), and Spiritually a Leader… You have 2 out of 3.”

Ouch Natalie, how rude. But that didn’t seem to discourage him. Not only was he not offended by my insensitive comment, but he actually mentioned how much he wanted to be all 3. He expressed his desire to grow spiritually in the Lord, that it was something he had been wanting, and that maybe I was what he needed to push him along. At the time, I am sure I was flattered, at the idea of how romantic it was that he wanted to make this change for me and maybe I felt special that I would be the one to change this bad boy, but this should have been a red flag.

Lesson Learned: Don’t be the main reason for someone to seek the Lord. Encouraging your boyfriend to pursue his relationship with Christ is a great thing, but if he is seeking the Lord just to get you or to keep you, then his heart is not truly transformed. His actions may change temporarily, but he will revert back to old ways as soon as he is challenged.

I was bored and he was there. This happened more than I care to admit. I don’t have a cute or funny story to tell. Just boring ones. So I am going to leave it at that.

Lesson Learned:
Don’t date out of boredom. You will be wasting both of your time that could be better spent elsewhere.

“I’m so confused!” was a phrase I remember saying often throughout brand new “relationships”. I couldn’t decide if I should be dating someone or not and it was constantly weighing on me! My heart was saying “yes”, but my head was saying “no”. What was the reason for this battle inside??? I was thinking with my lips… I had kissed these guys way too soon and with the introduction of this physical attachment came an attachment of the heart. Instead of being wise and looking at the situation realistically, I was looking at it with the heart eyes… not the love ones… the lust ones that come with this intimacy that made me think we had a real connection, when we really didn’t or that this person was a match for me according to God’s standards. As I look back and can see the spiritual maturity, the character traits, and lifestyles clearly, it shocks me that I was so confused. These were not matches made in heaven.

Lesson Learned:
Don’t kiss guys or become physically involved too quickly.

1.) It confuses the mind, keeping you from making wise decisions.
2.) It teaches guys that they can get a little bit of what they want and not have to commit to you. These guys were not pursuing ME, they were pursuing selfishness, whether it was just an ego boost or physical attention from a girl. Don’t be afraid you will lose someone if you wait to kiss them. If he is the right man, he will not be turned off by your desire for patience and purity, he will be impressed by it.

If you are over 25 and single, you have probably been asked “Ohh… why don’t you try E-Harmony or Match?” Most people assume that in your position, all you want is to be married and if God hasn’t made that happen yet, then you should make it happen yourself.

I remember reaching a point where I really realized that long term singleness could be in my future. In the back of my mind, though, I remember thinking, “Well if I am single by the time I am 30, I will do online dating and find my husband that way.” It was almost like it was a last resort, and also that it was a sure thing. Well around 25 or 26, after much prodding from other people I decided to try it out. I thought, at least I could have an answer for people when they “suggested” it and I could just say “Oh, I have done it and it wasn’t my thing.” Well I ended up talking with someone and we went on a few dates. I guess you could throw this guy in with the “he was there” category and we didn’t really connect in person. I realized that I had joined for the wrong reasons and because it wasn’t what God had called me to do, I had wasted this guys time and emotions.

Lesson Learned:
Don’t do online dating as a last resort or because someone is pressuring you. If God wants to use it to introduce you to your spouse, be open to it, but don’t take God out of the equation by using it.

We sat across from each other at the table at dinner. I stared at him, because he was so good looking and I was proud to have him with me. Then I realized it, we had nothing to talk about. Even though we had been dating for months, dinner was awkward. We didn’t have as much in common as I had thought, but I had been too distracted to realize that earlier. I never thought I’d be the shallow girl who dated someone for their good looks, but there I was. I had been trying to convince myself of these great qualities he had, but in reality I didn’t want to give up the arm candy.

Lesson Learned:
Don’t date someone or stay with someone for their good looks, prestige, or anything thing else outward. The Lord judges by the heart and so should we. We all know it, but looks fade, sometimes sooner rather than later, and what lasts will be their heart and their actions.

P.S. I am lucky… I just so happened to be with someone who is extremely handsome AND a complete package. I stare at him across the table getting a little lost in his baby blue eyes, but once I snap out of that we have amazing conversation and giggle the whole time we are together. :)

The Tattooed Band Guy
Don’t drive 4 hours away for the day with a guy you barely know.
The CIA Agent
Don’t believe everything you hear. Maybe he jumped out of a helicopter over a foreign land that he couldn’t mention and maybe he didn’t.
The One You Look at Rings With
Don’t automatically take steps toward marriage, because “it’s time” or you have been dating a while. Entering into marriage should be done intentionally and prayerfully, not just because it is the next step.
The Electrician
Just don’t… He will still be messaging you 5 years later… after 1 date.
The One with the Crazy Ex-Girlfriend
Don’t ever allow exes to take up any space in your current relationship. Move forward by protecting your future, letting go of your past.
The Blind Date
Always, always be quick to be honest if there are no feelings or connections on your end! It expresses such maturity and respect for the other person and their heart.

Before I end let me make a disclaimer. I am picking fun at all these guys, but the truth is they were all (almost all) really great people! I have tried setting some up with other girls and even became best friend with one’s wife. Hi, Mattie :) And the truth is that without them coming across my path I wouldn’t have learned all the things I have!

So now that I have bared my soul and told you about all my dating adventures, don’t leave me hanging.
What lessons have your exes taught you?

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  • Oh, this gave me a good laugh! I’ve dated quite a few of those you mentioned and I have to say I’m happy I eventually saw the light. In my mid-twenties I finally decided I was done dating. I didn’t want to say “never”, but the thought of being married or being in a serious relationship just did not sound appealing. I had not met a man in years that I cared to get to know below the surface and while my friends and family didn’t quite understand, I was happy being single and I put all my energy into growing my business. I moved back to my small hometown this past December and by January, I met the most amazing man. He is everything I never thought existed for me. I was patient and content with the status of my love life (even if I was 28 and unmarried – gasp!) and I fully believe that God brought J into my life when we were both ready. His timing is always best. This is also the first time Christ has been at the center of a relationship for me and with that comes a peace I’ve never known. Thanks for sharing your dating blunders – we’ve all been there! :)

    • Awww this made me tear up :)
      It is so amazing how God works. If only we knew all that He had planned for us those, the dateless weekends and the broken hearts wouldn’t hurt so much!!! So happy to hear about the man that He brought to you.. I have loved seeing your posts and have been curious ;) Keep us updated! Lol!

  • Ohhh Natalie, such a great post! Sadly, I can only relate to one – I dated one guy and I married him and we all know how that turned out! Haha ;) I’m getting to the point now where I’m excited [but still a little nervous] to officially start dating – I can’t even say dating “again” because I never really dated before! So I’ll be on the lookout for these guys, thanks for sharing and being so honest and open about your lessons learned!

  • I loved reading this post so, so much! I didn’t start dating until I was 19, but I think I’ve more than made up for it. Every experience has taught me a valuable lesson. I met the last guy I dated on Christian Mingle and the first few dates were spent immersed in scripture until he developed a super legalistic obsession with avoiding a physical relationship. It was incredibly awkward and left me in a real funk because it was somehow my “fault” for being the newbie Christian. It really taught me to look beyond just an intellectual understanding of the word and focus on how a man allows grace to work in his life.

    • Stephanie, that is so true! It doesn’t matter how much Bible someone knows, if he can’t apply it well to his life. The “rules” and the “grace” aspects go hand in hand. But I’ll be honest too and saying that navigating the physical aspect is so tough too. I can find myself struggling with the legalistic obsession with avoiding physical contact. I feel like the struggle with the physical is the “thorn in the side” of dating relationships. It will always be there, but it is a constant reminder that we need to rely on the Lord’s strength and guidance. So tough, but so worth it!

  • Thank you for putting into words what I could not, the “perfect” guy and the “perfect for me” guy are two different things and we shouldn’t feel guilty or feel like something is wrong with us. Family pressure can make it hard too, when all they see is the “perfect” guy but if it’s not there…it’s not there! Though it would be so much easier if it were. Trusting that God has a plan!