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Date and Fail Well

Couple standing in front of a lake at sunset.
A broken heart doesn't mean you guys did something wrong. Great pain comes from great risk— and so does great possibilities.

wrote a blog a few weeks ago that started a firestorm. In my post I explained the frustrations some of us Christian guys feel in dating. We assume “getting coffee is never just getting coffee.” Some of us fear that as soon as we ask a woman to coffee, and then especially if it goes well, she’ll start seriously evaluating us for marriage. And that’s a lot of pressure.

But then, being a good Christian man, I don’t want to hurt anyone; therefore, if I feel like there’s a potential reason I couldn’t marry this woman, I feel like I better end this now. Plus if I hurt her, it’ll affect our interactions around others and complicate my relationship with other women at church. So I have to know right now whether I’m likely to marry her, and if not, I better get out.

This is the pressure some of us guys feel as we try to lead a relationship, and under that sort of stress we tend to self-destruct. You can probably see how these situations reveal my own flaws and fears, but this is what I’ve felt.

Many of the comments in the blog were from girls who adamantly said, “No! Coffee can just be coffee! You are totally over-thinking it!” Over the years I’ve heard others argue that the best way to date is not to take things so seriously, take it day by day and see where things go. And sometimes that’s great because the comments on my previous blog also revealed everyone has different expectations.

Part of the solution may be communicating your expectations to each other as you start. In fact, I realized the reason I assumed girls were already thinking about marriage on the first date was because I was evaluating girls on the first date! Oh, the irony.

Coffee+ Dates

I’ve realized that sometimes, with some people, maybe coffee is just coffee. But something happened to me that validated my fear that “just getting coffee” really can end in pain.

My former girlfriend and I just ended a six-month relationship. Even though we shared pure intentions and our relationship had considerable potential, there were a couple things my marriage-bound mind identified as potential irreconcilable differences. But I tried to put those out of my head, and we decided to have coffee to see what would happen.

We tried to take it very lightly. We both liked each other, and I kept telling myself what I had heard: coffee was just coffee. But our coffees inched into serious dating, and within a couple months we started hitting against those differences I was afraid of. She could tell when I was concerned, and she gently coaxed out my concerns, which were huge disappointments for her and hurt her deeply. I started thinking, I wish I had never bought into the idea that a coffee is just coffee. This is too hard; I don’t want to keep hurting this poor girl. The relationship eventually ended. It was done with respect and kindness, and we’re still good friends, but I think we were both relieved.

The other day I was talking to a close friend of mine who was heartbroken over her own breakup that had happened a couple months prior. As she told me how much pain she was still in, I shook my head. I don’t ever want to hurt a girl like this, I thought. This could’ve been what I did to my ex-girlfriend. How could I ever consider “coffee is just coffee” if it leads to pain like this? How can I even try?

The pressures were welling up in me again. But then a thought hit me. I waited a moment, chose my words carefully and asked, “Does all the pain you feel make you wish you had never done it?”

She quickly said, “No, I’m still glad we tried.”

Heartbreak Doesn’t Mean We’ve Done Something Wrong

And that one statement shifted my whole perspective. I looked back and realized, despite the pain, I think both my former girlfriend and I would say we’re glad we tried too.

This applies to other areas of my life as well. If we try at something and people get hurt in the failed attempt, that doesn’t mean it wasn’t a valuable experience God can use in our lives. Without weighing in on God’s sovereignty versus free will or why He allows pain, I do believe if we try something that seems good and we fail, even if it hurts us or others, God still may have wanted us to try it (and He’s proud of His children for giving our best effort).

Even though I know coffee can be more than just coffee, it’s still worth trying. And if feelings get hurt, that doesn’t mean we’ve done something wrong. If you’ve always been the type to hold off because you’re afraid of the risk, remember great possibilities come with great risks.

If you see potential, consider stepping into it. If you feel the need, be transparent about your fears regarding relationships. Be ready to learn about yourself as much as you learn about someone else in this crazy dating process. Forgive (yourself and others) as much as you need to be forgiven. Attempt to always be humble. Seek counsel. Pray through it all.

Be ready for a roller-coaster because really good things can be really hard, and it’s often through the hardest times the deepest sanctification happens.

And there’s a good chance you’ll still be glad you tried.

Ross Boone is a writer/illustrator from Denver, now living in Atlanta. The desire to believe, despite living in this modern culture, is what compels him to search for creative answers. And he puts what he learns into words and pictures to share with others who might have similar questions. He is working on a Masters in Theology while he does freelance illustration and animation. His books and writings can be found at .

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