Uncomfortable Conversations


You’re listening to your friend describe the person he or she is dating and the thought bubble in your head is screaming, “You shouldn't be dating this person!” But you leave your friend’s company, having said nothing . . . and then spend the next few weeks having imaginary conversations about what you should have said. Or worse, you have conversations with other people instead of with your friend. How do you approach uncomfortable conversations? There isn’t a step-by-step guide, is there? But there are some things you can keep in mind before, during, and after.

Before the conversation . . .

Pray. Pray. Pray. Smother this situation in prayer—for wisdom, for humility, for timing, for the fullness of grace and truth. When you think you've prayed enough, pray a little more.

Identify your friend’s spiritual location. Where is he or she spiritually?  Would your friend say that he or she is a follower of Christ?  It’s absurd to expect someone who isn't living in the Kingdom to live by Kingdom values. They didn’t sign up for that (yet).

Understand the scripture “unequally yoked.” Read 2 Corinthians 6:14. This is the biblical go-to in challenging a believer who is dating a non-believer. Is this the situation with your friend or are you just not a fan of the person he or she is dating?

Examine your own heart. Ask yourself, “Do I want to be right more than I want God’s best for my friend?  Have I put in the time to build relational equity so my friend knows I'm on his or her side?  Is my heart broken for my friend or am I just angry?

During the conversation . . .

Think timing. Relationships aren't efficient. Adjust your expectation that you can waltz in, say a few lines, drop the mic, and walk out.  You might have the right stance, but is this the right time?  Also, big issues usually require more than one conversation.

Present God’s best. What does God want for us in terms of our dating relationships?  Focus on what Scripture says about dating wisely.  Avoid your own commentary or Christian cultural “deal-breakers” about how dating should look.

Ask questions. Ask questions. Ask questions. Asking questions allows you to lead your friend to the answers, rather than telling him or her the answer.  It helps identify the tension in being unequally yoked.  Telling someone what to do or think is condescending and patronizing. Questions to ask your friend to help identify the tension:

  • As you’ve talked about your faith with your significant other, what have you heard that’s encouraged you?
  • Have you identified your "non-negotiables"? These are values you won't compromise in a dating relationship.
  • Are there areas you’d like to see him or her grow in relationship with Christ?  Could you marry your significant other if nothing changed?
  •  What would you tell someone in your position?
  • If the most important thing in your life is something you can't share with your significant other, how will you build intimacy?

After the conversation . . .

Encourage courage. Most single people don't date non-believers because they “don’t know better.”  It’s not a lack of knowledge, but a lack of courage.  Pray and encourage your friend to have the courage to be obedient to God’s best for his or her life.

Walk with her or him. Regardless of what your friend decides, walk alongside her or him.  You can represent God’s truth even when you don’t approve of your friend's behavior. God did the same for you, didn’t he?

Did I mention this won’t be easy? I'll be back next week to delve into this topic a little more deeply. In the meantime, how have you navigated uncomfortable conversations?