Talking About the Hard Stuff in Dating (Without Making It Awkward)

Dating is fun… until it’s not. Let’s face it, some conversations are just plain awkward. Whether it’s talking about boundaries, figuring out where things are going, or bringing up something that’s been bugging you, these moments can feel like walking on eggshells. But here’s the thing: talking about the hard stuff doesn't have to be so terrible. With a little thought (and a lot of honesty), you can tackle tough topics without things going sideways.

Pray First (It Really Helps)

Before you dive into a tricky topic, take a second to pray. Ask God to help you stay calm, choose your words wisely, and listen with an open heart. James 1:5 says, “If any of you lacks wisdom, you should ask God, who gives generously to all without finding fault, and it will be given to you.” Even a quick, “God, please be with me during this conversation,” can make a difference.

Pick the Right Moment

Timing is everything. Don’t drop a heavy topic in the middle of a fun date or when one of you is stressed out. Instead, find a time when you’re both relaxed. A simple, “Hey, can we talk about something when you’re free?” gives them a heads-up without making it sound like a big deal.

Be Honest, But Don’t Be Harsh

Honesty is important, but how you say things matters. Instead of pointing fingers, talk about how you feel using “I statements.” For example:

• Instead of: “You’re always late, and it’s so annoying.”

• Try: “I feel unimportant when I’m waiting around for you. Can we figure out a way to fix that?”

This keeps the conversation from turning into a blame game.

Actually Listen

It’s easy to get caught up in what you want to say, but don’t forget to hear them out. Proverbs 18:13 says, “To answer before listening—that is folly and shame.” Let them share their side, even if it’s not what you were hoping to hear.

Keep It Relaxed

Not every serious conversation has to feel like a big deal. Smile, crack a joke if it feels right, and remind them that you care about them. A little humor can make things feel less intense and more like a team effort.

End with a Plan

Before you wrap things up, make sure you’re both clear on what’s next. Whether it’s setting a boundary, making a change, or just agreeing to keep talking, clarity is key.

Awkward conversations don’t have to ruin the mood. In fact, they can bring you closer when you handle them with honesty and care. So take a deep breath, say a quick prayer, and remember to speak the truth in love.