All Is Not Fair in Love: Reminiscences on my Relationships up Till Now

I remember a basketball practice during eighth grade. In between layup lines and passing drills, one of my friends on the team was getting me mentally prepared for my first ever date. A week or so prior, I had been frantically tracing this girl around the field during P.E.—a girl who was ever so special to me—incrementally working up the courage to ask her out. Realizing that my window of opportunity was coming to a close (because, obviously, you can’t ask a girl out except during P.E.) I finally rushed the question out in one gasp, “Hey I was wondering if you wanted to maybe go out with me?” and much to my shock she said she would be willing (it was around Christmas and she must have had a charitable spirit). Well, as fate would have it, our eighth grade class had collectively decided to go see School of Rock that weekend and as a result, I could go to the movies with my leading lady without having to break the news to my parents that I was sorta kinda going on a date.

So my friend and I are at practice and he’s grilling me with the important questions: “Andy, when during the movie do you put your arm around her shoulder: “beginning, beginning-middle, middle, middle-end, or end?”

“Middle?” I hazard.

“Beginning-middle,” he replies, confidently, and I take a mental note to find out the run time of the movie, divide by five, and add to the movie start time.

We’re at the movies and the minutes are creeping along—we must be getting close to the middle by now—and I’m feeling like a complete failure because thus far I haven’t fulfilled my vital duty by putting my arm around her shoulder. Ever helpful, my friend whispers to me just loudly enough so that everyone in the theatre can hear: “Andy, your arm!” all the while frantically and exaggeratedly making a gesture like he’s stretching his arm over an imaginary girl’s shoulder. Well, of course my date hears this so there’s no backing out now—this is the moment of truth—so I try to nonchalantly extend my left arm over her shoulder. She’s gracious enough to smile kindly and say “no” when I ask her if she minds. And with that my dating life is off to an illustrious start! I even had the privilege of holding her hand later on during the show.

My sophomore year of high school I had eyes for a runner on the cross-country team. She was the fastest girl on the team (I’ve always had what runners refer to as “speed-goggles”) and I was positively smitten by that ponytail and million-dollar smile. I professed my love to her right after she had finished running a 5K on a super-hard course and I think after I got done with my speech she winced and said something to the effect of, “Thanks.” A few weeks later, I got a buddy to pick up some flowers for me at Safeway (because he could drive) and I asked her if she would like to go to the Winter Formal with me. She politely declined, saying that she had already made plans to go with friends.

Well, from this point on it wasn’t too pretty. I must have figured at the time that if I only sent enough dramatic e-mails, surely she would come around and see what I swell guy I was. I actually still have these e-mails and I brushed them off recently to reminisce about a teenage crush. All I can think after reading them is: “What a cocky tool I was!” I guess I thought that the occasional bad word for effect made me cool and that every other e-mail had to have a Notebook-esque love speech.

As I reflect on it now, I realize that at the time I actually thought I was one of the proverbial “good guys.” I thought that she didn’t like me because I wasn’t handsome enough, or strong enough, or bad enough and it was my responsibility to help her see past all that to my tender heart. The trick is, the tender heart wasn’t actually there. The evidence of this is how I treated her after she turned me down. If I truly cared for her, I would have wanted whatever was best for her, which, clearly, wasn’t a relationship with me. Instead, I wanted my own happiness, even if it came at the expense of hers. This became glaringly obvious after she started to date another guy and I wrote something of a battle-rap calling him out in an independent school newspaper. I totally wrecked her feelings and yeah, I felt bad, but probably if I’m being honest I felt bad because I had been a fool and everybody knew it.

I went to a small high school and when I got to college I found out that there are other fish in the sea, as they say. It took me all of about two months to jump into a relationship and another one to jump out. And my “jump out” I mean “get dumped.” My girlfriend broke up with me on a Monday, which just so happened to be the same day as the Williams cross-country team’s infamous Euro Trash party. It’s very Euro and very trashy. Being the big-shot that I was, I asked a few of the prettiest girls in my entry if they would go to the party with me. When we got there, with my arms around the shoulders of all four girls (clearly I had learned from middle school), I proceeded to introduce them one-by-one to the girl who had dumped me earlier that day. Then, a few hours later, I made out with another girl on the dance floor. I wasn’t drunk, I wasn’t particularly depressed, the honest truth is that I just thought I was a big deal and I was going to show so-and-so just what she was missing.

About this time—and after all these years I’m still not sure exactly how to phrase this—I started to grow in my faith. Perhaps the best way to put it is that it felt like God was inviting me into deeper, more meaningful relationship with Him and I just tried to say “yes” whenever I could. Even though I had gone to church for about seven years, for the first time in my life I sensed that God was asking me to listen to Him, to take steps of obedience. And further, for the first time in my life it occurred to me that perhaps my identity as a Christian should in some way influence the way I went about dating relationships.

I was really good friends with a girl in my entry during our freshman year and at times my heart was inclined to hope that we could be more than friends. But she was already in a relationship and I wanted to try to honor that. I tried to separate my feelings from my actions as much as possible out of respect for her relationship. Looking back, perhaps there were times when we stepped outside the bounds of what I would consider okay for two friends if one of them was already dating someone else. It’s hard to say. We remained really good friends throughout our freshman year and picked dorm rooms next to one another for the following year.

But when our sophomore year started it was clear that something had changed. When we spent time with one another, it always felt awkward and forced. It seemed that she didn’t want anything to do with me. In addition, during our freshman year I had invited her to join me when I went to Freshman Bible Study and Friday Night Fellowship. I felt like she was really growing in her faith. But when we stopped spending time with one another, she also stopped attending Williams Christian Fellowship events. At one point she confided in me that she felt like I was hypocritical—vocal about my faith on one hand but saying and doing some unkind things on the other. I was heartbroken. To be sure, what she said was true. As I mentioned earlier, this was the first time in my life that I had allowed my relationship with Jesus to affect the way I lived. But the heart is such an obstinate thing. It really takes time to change and my heart was still inclined to do the things and say the things it used to say and do.

Over the course of that semester I apologized to her many times. I apologized for not living out my faith better, I apologized if I had not respected her relationship enough, I apologized for apologizing too much. I spent a lot of nights in my dorm, sitting in the darkness and crying and trying to hear God’s voice through it all. I wish it wasn’t true that I had cried but the fact is that love or infatuation or whatever you want to call it is a very strong emotion. We as humans weren’t meant to be alone and we’re always searching for companionship. But as I sat there quietly, I sensed that there was a God who cared about me, and who cared about my relationships, and who wanted for me to be happy and to find my helpmate.

It just wasn’t the right time. My heart needed a major renovation first.

I felt like I needed to take a step back before I could take a step forward. I had learned a lot about dating—from my friends, from my parents, from culture—was any of it good? Was any of it worth holding on to? What did it mean to love women because they are made in the image of God and not because they could temporarily fill a hole in my heart and make me feel happy?

I made it a goal that for the rest of the year I would treat girls as friends first and foremost and not as potential girlfriends.

Throughout that year, I made more friends than during any other year of my life. It’s amazing how freeing it was to get to know people and love people simply because they are worth loving and worth getting to know and not because if I played my cards right I could take her out to dinner and a movie next Friday night. Honestly guys, I feel like girls can tell when you are simultaneously getting to know them and sizing them up as a potential date. It really cheapens the interaction. And girls, vice versa. The simple fact is that what most girls need is not another potential suitor, not another guy to hit on them, not another guy to tell them they’re pretty. Instead, what they need is a brother who will stick up for them when other girls are tearing them down because of how they look or what they’re wearing. They need a brother who will protect them when other guys are sizing them up, treating them as another notch in their belt. They need a man who will listen to their hopes and aspirations and help them get to where they want to be. We need more brothers and less lovers.

A lot has changed for me over the last five years. I’ve only been in one relationship since then, and I’m overjoyed with that relationship and where it’s heading (for those that don’t know, I’ve been married to my amazing wife Kelsey for two years now). I believe that my heart has been changed by God for the better, that I’m not the guy I once was (though that guy comes back occasionally). But those are stories for another time.

So why do I write this, opening my heart up and sharing these (often embarrassing) stories?

I write to apologize to the women I’ve hurt because of my selfishness. I put my desire for a relationship above your well-being and for that I am sorry. But I also write in recognition of and thankfulness for the journey, that “I wouldn’t be the man I am today / If not for those I’ve loved along the way.”[1]

I write to advocate for a new approach to relationships for young men and women. The predominant message of American culture is that every woman (or man) exists for your enjoyment—all you have to do is go out and get them. This message ultimately leads to broken hearts, fractured relationships, and distrust between the sexes. Do we just not believe that all the heartache and pain is worth it if only we can have that one-night stand? Do we not have faith to believe that the things that we do and say have lasting impact on our character and our hearts? Why are we so enthralled when James Bond sweeps the girl off her feet and then leaves her to pick up the pieces the next day? I’m not against infatuation and twitterpation and that awesome butterflies-in-your-stomach feeling when that special someone catches your eye. But even as we embrace and enjoy the emotions, let’s be truly kind and truly charitable in our actions. Let’s take a step back from flirting, from pursuing, and practice the sacred art of friendship. C.S. Lewis describes friendship as the “instrument by which God reveals to each of us the beauties of others.” May we become experts at uncovering all of the myriad beauties in the people around us.

Finally, I write in gratitude to God because I sense that he’s been quietly, slowly, and creatively authoring transformation in my heart. He let me try to love others in my own way and I turned out to be absolutely rubbish at it. The old me never could have been trusted with as precious a gift as my wife: I surely would have ruined us. But if we stay close to Him, following His example of sacrificial love along the way, we just might have a chance.



  1. Very nice, Andy. Thanks for sharing. You’re writing really flows and is easy and enjoyable to read.


    1. Appreciate it, Mr. Riegg.


  2. I am currently writing notes and comments in my childhood journal as a gift to my son. “Cocky tool” is exactly the word I was searching for. ..thanks for that


    1. Yeah, it does kind of have a nice ring to it, doesn’t it? That seems like a cool project!


  3. […] A couple weeks ago I wrote about my dating history and how even when I was “in love” with a girl I did not treat her lovingly, especially when my love was unrequited. I spoke about how I felt like I needed to take a step back from pursuing women as potential partners and see them first as friends so that God might be able to do some surgery on my heart. As a result, during my sophomore year of college I (mostly) abstained from flirting and pursuing and saying “hey you” and whatnot. […]


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