Reflecting on My Years of Singleness

Today is my boyfriend and my third year anniversary! It’s crazy for me to think that it was three whole years ago that I was freaking out, wondering if he would ask me out and what I would do if he didn’t.

I shared a bit of our story three years ago when I announced that we were dating. But today I want to share the whole story. The good, the bad, and the ugly.

Mostly because I love reflection. And because I want it all to be in one place. But too, I want to share it so you can know that if you struggle with singleness, you’re not alone.

This is a longer post than I normally write because I didn’t want to leave anything out this time. If you want the shortened version, you can find that here. :)

This is the story of how Kara and Caleb didn’t date…

Caleb and I first told each other that we liked each other in June 2014, a month after we graduated high school.

During that conversation, I asked him what we were. (Oh the joys of a “define the relationship” talk.) He said we were best friends who would probably start dating at some point in college (we were going to the same university).

Well, freshman year came… and we didn’t start dating.

However, we saw each other almost every day due to having class together or getting lunch with our mutual friend group.

During that time, our friendship grew and strengthened beyond what it had been in our high school/ youth group bubble.

We started intentionally setting times aside to hang out, such as when we would go back to his dorm’s common area to watch Once Upon a Time every Monday after biology class.

We would hang out just us some and hang out in groups with our friends.

My roommate and friends thought it was weird that he hadn’t asked me out yet. And often I would wonder about that too. I even got up the nerve to ask him about it a few times.

I distinctly remember Caleb looking at me, smiling, and saying, “Trust me.” At that moment, I realized I did. (More about all that in this post.)

So we stayed single.

And I decided that during that point in my life, it was a good thing that I was single anywho. I was able to create some awesome friendships during that first year of college. I was able to adjust to college life and living on my own for the first time. And I was able to get involved at my church.

Now, granted, it is possible to make friends, adjust to college, and get involved at a church WHILE dating. I’m just saying that I’m grateful that I was able to do those things without also having to learn how to date.

Additionally, I was going to Costa Rica for a month after freshman year and I knew it would be hard to date during that. He also had a few things going on in his life (that I don’t want to write about here) that made it good that we weren’t dating.

Sophomore year was probably my hardest year of college.

My best friend at the time suddenly and unexpectedly transferred schools and I struggled A LOT with that.

These posts came from that time if you want to read more:

• 22 Verses for the Brokenhearted
• God is Good ALL The Time
• The Joy of the LORD is Your Strength
• Beyond our Wildest Dreams

During that time in my life, I found myself feeling relieved that I wasn’t dating. I found myself missing my friend so much that I couldn’t even fathom what it would be like to go through a break-up and lose Caleb too! I couldn’t bear it!

But then my car wreck happened.

I don’t want to get into the details in this post, but basically, I could have died. My parents were out of town and so I called Caleb and let him know. He literally rushed to my side, followed the ambulance to the hospital, held my phone so I could call people and let them know and sat with me while I waited for test results.

The wreck freaked me out and brought me all kinds of anxiety. I realized that anyone could die at any point, and I started worrying that either Caleb or I would die before we could date and fall in love. I started wanting to date him again, but for the wrong reasons.

It also was occurring to me that we couldn’t be friends forever unless we got married to each other. If we got married to other people, we could probably still be friends but it would probably be really weird considering how much I would have liked him in my past.

I confessed this to Caleb at one point during the cruise I took with his family (read about that trip here!). In response, he chuckled and said, “Don’t worry, I’m pretty sure my mom has been planning our wedding for years.”

Oh goodness.

But during that conversation, we established that we still mutually liked each other and he said yet again that he would ask me out someday.

This was a year and a half after he first said those words.

I felt excited about him someday asking me out… but I also felt skeptical.

At some point during the spring semester of sophomore year, I convinced myself that he was never going to ask me out and I should just “get over him.”

Summer started and Caleb and I didn’t see each other much.

Another guy started texting me, and after a few weeks of talking, he asked me out on a date. I said yes, and he and I went on two and a half dates together.

Through going on those few dates, I realized that I didn’t want to date people other than Caleb yet. I didn’t know if Caleb and I would work out, but I didn’t want to never have the chance to find out.

I felt like this other guy was moving way too fast for me. Yet, I still felt like Caleb was being too slow. At one point, I remarked to one of my friends, “I just need someone who’s in the middle! Not too fast, and not too slow!”

When junior year started, I sat Caleb down and straight-up asked him, “What should I do if some other guy asks me out?”

He responded, “Well since we’re not dating yet, there’s nothing I can do to stop you. Yet, in my heart, I’m screaming ‘No don’t do it!’ but I won’t stop you.”

I then told him about the guy who had asked me out and told him I went on a few dates with that guy.

As I look back on all of this, I admire Caleb’s response so much. He never was the kind of guy who led me on and acted like we were dating when we weren’t. During our time of singleness, he treated me with honor and respect. He never claimed possession of all my time and he wouldn’t touch me- not even a hug.

Sometimes I hear about other girls who have guys who are fake dating them. And for a while, I worried that Caleb and I were fake dating. But I see now that we really weren’t. We were legitimately best friends who happened to like each other. We didn’t voice our liking of each other very often so it wasn’t the focus of our friendship. Instead, we just focused on being friends and learning more about each other and having fun.

Okay, back to junior year…

That semester I participated in my university’s pageant. (More about that in this post.) I was crazy busy with that and an internship at a local high school. He was pretty busy with school too, but we still found times to hang out.

During the fall semester of that junior year, during all that craziness… I remember feeling peace about Caleb and I. It was as if I had finally learned how to truly view singleness as a blessing. I decided that maybe I needed that season of singleness– if for nothing else than to encourage people who were reading this blog.

However, even during the most hopeful of times, there was still that little seed of doubt that would pop up every now and then.

Which leads me to December 2016.

I remember Snap Chatting my best friend one night during Christmas break and lamenting to her that Caleb was never going to ask me out. She comforted me some and then said, “How about you write ‘Are you ever going to ask me out?’ on a clothespin and put it on his car?”

I thought that was perfect!

You see, clothespins are something Caleb and I have played “war” with since our freshman year of high school! We would pin one on the other and try not to be the one with the clothespin.

Clothespins are how Caleb asked me to both junior and senior prom. I asked him to go to Spanish Club’s salsa night with me during our freshman year of college with clothespins.

So my friend’s suggestion to ask if he was ever going to ask me out by using a clothespin seemed perfect.

Was I acting out of impatience? Yes.
Was I trusting God? No.

But I didn’t see that then.

After a big long adventure that is detailed in my journal but too long to write here- I pinned the clothespin to Caleb’s car.

And then I went home and waited.

Later that night he texted me about something else, and then said, “Oh, and the answer to your question is ‘Yes, I will’.”

Instead of giving me the peace I had been hoping for, his answer drove me to tears.

Sobbing that I would have to wait forever and not knowing if I had the strength to do that.

 See my problem? I had turned to Caleb and the hope of dating him for peace instead of turning to Jesus. At that moment, I forgot all of what God had been teaching me about singleness and trusting Him. I felt hopeless and utterly impatient.

At my mom’s suggestion, I finally replied to his text, “Caleb, I need a timeline.” This was the first time I had ever demanded to know when he would actually ask me out.

I fell asleep that night praying that I would be fine if he said he wouldn’t ask me out until after we graduated college.

The next day, I started my period and felt a bit better knowing the sobbing of the night before could be partially blamed on hormones.

Then I got the text containing Caleb’s reply to my question: “Within a month.”

My heart stopped.

I read it again and again, shocked.

I was not expecting that.

Dumbfounded, all I could reply with was “Cool, thanks.” which I still consider to be the lamest text I have ever sent.

Flash forward a month to January.

The “Within a month deadline” was drawing closer and closer. I remember stressing out about it to my roommate: “What do I do if the month ends and he still hasn’t asked me out??? Do I end our friendship? Give up again? ‘Break-up’ with him?? How do you break-up with someone if you were never dating?”

I remember repeating the words to Proverbs 3:5 over and over as I walked to my classes. “Trust in the Lord with all your heart and lean not on your own understanding.”

On January 22nd, my roommate and I were going to go get pretzels from the mall. When we got in her car, she told me she needed to run by my parent’s house to pick up something from my dad for her brother (my family lives 15 minutes away from my college).

I said sure, but that we should go to the mall first to get our pretzels since it was on the way.

She refused and said, “No, let’s go to your house first.”

I argued with her about it a bit, not understanding why she would waste gas like that. Finally, I said, “Whatever,” crossed my arms, and thought to myself, it’s her gas.

When we walked into my house, I was greeted by a trail of yarn with clothespins scattered along it.

The clothespins spelled out the following:

When I reached the end of the trail (which went all over my parents’ house), I ended up in the game room. Caleb walked out from behind the door, holding daisies in his hand. “Will you go on a date with me?”

“Yes,” I replied, “It’s about time!”

And, thankfully, he laughed at my blunt comment.

My roommate, who had been filming me the whole time, pointed her phone at me and asked, “Are you still mad at me for not taking your suggestions at how to get to the mall?”

It occurred to me that she must have been in on this all along. “A little bit,” I retorted.

Later that day I asked Caleb if we were just going on dates or if we were now boyfriend and girlfriend. He said boyfriend and girlfriend, and then we made it Facebook official that we were dating. (Is that even a thing still haha?) A week or so later, we went on our first ever date!

The morning after he asked me out, I woke up and thought the whole thing was a dream. I checked my phone and I had a ton of Facebook notifications. People were commenting on the post announcing that Caleb and I were dating! That meant it was real! Some people said nice things like “Congratulations.” Others said things like “Finally!” or echoed my thoughts that it was “about time.”

Those comments annoyed me, but I couldn’t think of why.

Finally, I realized its because most of the people commenting things like “Finally!” didn’t know Caleb and my story. They were just friends from high school that knew we liked each other back then and so we were “finally” dating in their minds. But those people didn’t walk through those two and a half years of singleness with me. They didn’t know how frustrated I got. They didn’t know that I was ready to give up- again!

A few months ago, Caleb confessed to me that he was worried I’d say “no” that day when he asked me out. “I was worried you’d say, ‘Nope, you made me wait too long. Not interested’.”

Personally?

I’m glad I waited. 

Caleb is a truly incredible guy. He is patient with me when I freak out about things. He offers me advice and tells me truths that I might not want to hear but need to hear. Caleb accepts me for my weirdness. He is totally weird and awkward himself, which I find adorable and attractive. He loves Jesus and is currently studying theology so he can become a youth pastor. And he makes me laugh. I cannot imagine my life without him nor do I ever want to experience life without him.

I chose not to date in high school, so I don’t really count that time as a “single season.” Really, I was only truly single for two and a half years. If Caleb and I get married (which I hope we do!), then that is the only period of true singleness I’ll have in my life.

I honestly feel kinda guilty about that.

There are girls I know who have been single way longer than I was. Their story is different than mine… and I feel like I no longer can reach out to single girls and be an encouragement to them because I’ve now been dating longer than I was single.

So, no, I might not be able to advise single ladies who are older than I and have been single longer than me.

But this I can say:

Each season has worth. Each season has value.

So don’t covet someone else’s season.

I look back on those years of singleness and wish I hadn’t stressed so much about whether or not Caleb and I would start dating. I wish I had enjoyed it more for what it was. And I wish I had trusted God more fully.

And now, as I hope for an eventual proposal, I’m reminding myself of these truths.

God is good, regardless of your relationship status. Because in the end, the most important relationship is the one you have with Him.

So, no matter if you’re single and waiting for a boyfriend or dating and waiting for a proposal- trust God with all your heart. He knows what He’s doing. ❤️

Posted by Kara Beth & filed under My Life. This post has one comment.