The Long Road to Marriage: All of My Dating Distasters

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It’s one thing to hear ‘Hey – you should write a book!’ It’s another thing altogether to hear that after sharing yet another tale of my dating disasters.

It was a long, bumpy road, the path to marriage. And boy, do I have stories.

I guess it all starts with the chubby little girl with glasses that was me. Sadly, I have a long history of broken hearts. I don’t know why, but even then, I was always worried that I wouldn’t get married. That was always a fear I carried with me.

The chronicles go way back to elementary school. First, there was A., my childhood love. What began as a little-girl-crush grew into a big-girl-junior-high-and-high-school crush. Yup, I was convinced we were meant to be, and we would get married when he came to his senses. Well, he was married before I graduated high school.

Well, no fear – there were others along the way when I got tired of waiting. There was B., my first boyfriend in 6th grade. Then there was C., my second boyfriend in 7th grade. Apparently, I was on a roll.

Suddenly, things got quiet, and I hit a dry spell. Sure, there were little (or big) crushes here or there. Sometimes I was the one with the crush; sometimes I was crushed on. But it was a boyfriend wasteland from 7th grade until my senior year. And somehow, that heightened my fear.

Enter D. in 12th grade. If I could put a name and face to typify my dating debacles, this one would be my crowning achievement. What started out as ‘friends,’ then ‘best friends,’ then ‘he’s dating my best friend,’ then ‘he’s dating me’ evolved into a 10-year saga.

If I have one regret in my dating past, it’s that I didn’t wise up sooner. It must have been excruciating to watch from the outside…like a train wreck…you just can’t look away. This relationship was always in the background throughout college and my 20s…never-quite-on-never-quite-off.

Throughout those years, while this sad-country-music-song-relationship became the white noise of my existence, there were a few promising possibilities….

There was E., a missionary-kid I was set up with on group blind date in college. Now E. – he really was a stand-up guy, but I think I was too shallow at the time to know it.

There was G., one of my best friends in college. There was always that ‘liking-each-other’ tension, but we could never figure out if we really did like each other. This went on for a number of years – even after we graduated. Either he was involved with someone or I was…never quite got the timing right.

Then there was H., a cute southern distraction in my senior year. H. was a really nice guy, too – but because of my other relational drama, I don’t even think I gave him a fair chance.

I’ll be honest. I was a little shocked that I walked out of a Christian college and hadn’t found anyone yet. I thought they pretty much guaranteed that when you enrolled. I wasn’t quite panicking yet, but it was on the way.

That summer, I met I., a youth pastor from N.J., at a youth camp I was chaperoning. I thought, for sure, that this must be it. He even gave me his sweater to take home (sigh). But within a few months, that ran its course.

I was in full-time youth ministry at the time, and I thought, ‘For sure, if there is ever a place to meet eligible Christian guys, it’s in youth ministry!’ And it was true…they were always crossing my path. There was J. from Indiana who came to NY to visit me, and then there was K, part of a traveling evangelism team who was something of an intriguing but peculiar guy. But for one reason or another, they were all just a flash in the pan.

Then, across my path came L., a handsome new youth pastor in town. We had a whirlwind summer romance…which burned out by fall.

As I got older, the pickings got slimmer. But not to fear…at this time, a nifty new invention entered the world which would change the face of dating forever: the Internet.

Yes, I went there, too….E-harmony, Christian Mingle…my profiles are probably still hanging out there. First, there was M., an English professor from Missouri who would ‘take me for drives’ while we were on the phone. I used the ‘God told me I needed to break up’ line on him. (Please. I know).

Then there was N., a sweet guy from NYC…maybe too sweet. On our second date, he brought me to a pier on the Hudson River…with his guitar…to sing to me. (Awk-ward).

And there were a few guys I met from my area. There was O., who took me to see a strange Chinese Christmas play in the city. I really thought he might have potential…but I remember one time he took me out for lunch and held my hand when we prayed for the meal. After he dropped me off, I cried the whole way back to my classroom. Yeah, probably not a good sign.

Then, there was P., a handsome, godly brother of a friend. A nice little group of us were hanging out, having Bible studies together…he seemed so great…until he became interested in my best friend. Ugh. Fail.

At this time, I’m sure the stars aligned in such a way that my heart was just ripe for disaster. There were a few more significant relationships after all of this that put my hopes over the edge.

I met Q. at church when I was 28, and I was somewhat swept off my feet. What seemed really promising went south pretty quickly; the red flags were there early on. The relationship lasted for about 8 months, and we probably should have broken up sooner. Why didn’t we? This is probably about the time when I started to panic.

I was 28 and just wanting to settle down. I had a decade of strings of relationships or promising starts – that all went nowhere. I wanted it to work so badly with Q. – I think he did, too, but we just didn’t know how to pull it together. All of the signs were pointing to the exit. I knew I needed to get out but lacked the strength. In (another) fight the night before the first day of school, God showed me the door, and I took it. I was relieved, but my heart and soul was in shreds. I’m not sure why this devastated me like it did, but I was a disaster. Just tears all the time. I look back, and ugh, I was a mess.

Finally, my heart healed, and as chance – or what I was convinced was God – would have it, I got reacquainted with R., an old friend and old crush. Of all my crushes, he had been my favorite. My ideal. My perfect match. And finally, it looked like everything was coming together. It seemed like it was just on the cusp of becoming a reality …until, I found out – on my 30th birthday…that he had started dating someone else. Happy birthday to me – welcome to the 30’s.

Now I understood why they called it a ‘crush.’ I was. Again.

Not to be kept down for long, I met S. later that year – if you count ‘online chatting’ as meeting. (I also met up with T., my friend’s relative from Nebraska, and U., a hottie from college who I was ‘matched’ with on dating site.) Of all 3, I liked S. the best. We clicked instantly and when we met for the first time, the connection was real and substantial. The situation was complicated – he was divorced with 2 kids and lived in Canada. (Minor issues, right?). But I was hopeful and hadn’t felt like that in a long time.

We were still in the ‘getting-to-know-you-but-I-really-liked-you’ phase when the bombshell dropped. S. was diagnosed with stage 3 basal cell carcinoma. Cancer. Of course, the relationship was on ‘hold’ status while his life was on the line. But me being me, I jumped in emotionally to give him all the support he needed. I prayed my heart and guts out like I never have before. The healthcare system in Canada isn’t what it is in the U.S., and his treatments and appointments were delayed for weeks at a time. It was one of the most emotionally draining and traumatic periods of my life. And man, was I wrecked when all was said and done.

In the end, he came through cancer, but our relationship didn’t. I understood why he couldn’t commit, but I was devastated on every level possible.

And after that, finally, I was done. I was done dating. Done trying. Just done. My heart just couldn’t take any more. All of these failures, all of these disappointments.

I finally decided that if God wanted me to get married, God could arrange it. But I was done putting in any kind of effort. Done trying. Done putting myself out there. Just done.

But, as it turns out, while I was done – God wasn’t.

To find out what happened next, click here!