Relationship Challenges? 8 Questions to Consider


photo: Thomas Yang


When I first got engaged, I often got asked how I knew my eternal boo was, “the one.” Now, this is a big question – and I have to say there wasn’t one exact moment, but many little moments that culminated in the feeling that me and homeboy could rock out forever and grow into a duo of super ultimate old people.

In my observation, typically when someone is asked a question of this nature the answer goes something like, “well, he’s just so sweet and he makes me laugh and he has such a big heart and we ride off into the sunset on unicorns together every night after he makes me fresh baked cupcakes which he spices with a single tear from his eye after reading me the haiku he wrote me while chopping wood and lifting super heavy things because he equal parts sensitive and manly.” All of which is totally true for me (except for one part- that’s right, the cupcakes are actually store bought. Can’t have it all, I guess).   

The reality is as as wonderful as those things are,  one of the big things that made me sure I’d picked the right dude was what happened when the sunsets gave way to cloudier skies…

Early on in our courtship, we went through some pretty big challenges, ones that required us to be intentional about where we were headed as a couple. Many times in our dating/relationship culture we are told to focus on the challenges that arise. We focus on the fact that there is a problem and we let that be the indicator as to whether or not the relationship is viable. To some degree, that’s valuable. If you’ve got 99 problems and your significant other is all of ’em plus one – well that’s an issue. However, I find it useful not to focus on the fact that there is a problem but, rather, focus on the response to the problem.


I figure there will always be problems. They will pop up when we least expect them. You will be the problem sometimes. He will be the problem sometimes. Crap happens. Such is life. Focusing on the mere fact that there is a problem is actually quite unhelpful.

When we faced this first particular challenge I was interested in what his response would be (and I’m sure he was interested in the same for me). I payed attention to things like the following:


Does he/she seek to understand or just seek to be right?    

What are the steps he/she takes to bring about change?

Can we be honest with each other?

Does humility play a role in assessing the issue & remedy?

Is he/she still thoughtful and respectful in words and actions even though things are tense?

Can he/she articulate what’s going on with him/her or do you have to guess?

Can we resolve conflict in a healthy way?

Am I giving those same things in return?


These things were really important for me as I’d been in unhealthy relationship situations before. Conflict terrified me because it had always been harmful & hurtful – blame game. This, however, was radically different. We were both as self aware as we could be as two imperfect people working to find a solution that was healthy for the both of us. He still listened to me. He still cared for me. He still made me feel like I was safe to share my thoughts and feelings. That showed me more about weather or not this was a relationship with potential than any perfect sunset or cupcake ever could. This can really apply to any relationship, be it romantical or friendshipy – both of which are real words.

I’m not naive enough to think that every roadblock we hit will result in a completely kumbaya type resolution – but I know that we have the tools to encounter trouble and make it through. A mark of a good relationship is not that you never run into pools of crap – but, rather, when you do you’re both willing to put your waders on, hold hands, jump in, and get to the other side together. So cheers to the challenges, friends. They tell us more than any cupcake ever could. 

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