Dating is a journey, not a life sentence. Some connections sail for a season, others for a lifetime. But how do you know when it’s time to dock the boat and step off gracefully — whether after the first, fifth, or fiftieth date?
Here’s the good news: this doesn’t need to be a complex algorithm with charts, spreadsheets, or a full-blown nautical science team analyzing the radar. It can start with one simple question:
“Did I enjoy my time with this person enough to see them again?”
That’s it. Not: “Can I see our entire lives aligning forever and ever?” That’s way too big of a question for the early stages. Dating is discovery, not destiny on day one.
Of course, let’s be clear: if you see a red flag — addiction, anger issues, unresolved trauma they refuse to address, abuse of any kind — that’s a hard stop. No need to ask any further questions. Disembark immediately.
If there are yellow flags, proceed with caution. Keep the radar on. Keep asking questions. Keep inviting your trusted circle to help you discern. But in the early stages, the compass can stay simple: “Did I enjoy my time with this person enough to see them again?”
When Dating Becomes Exclusive
Once you and the other person have moved into a committed dating relationship (meaning you’re only seeing each other), the question naturally deepens. It may sound like this:
- “Am I growing closer to Jesus with this person?”
- “Do I feel more peaceful and more myself in their presence?”
- “Am I experiencing the kind of partnership that makes me excited to navigate both calm seas and storms together?”
- “Do we share rhythms, values, and vision that make life feel sustainable and joy-filled?”
- “Is this relationship helping me love God and others more fully?”
Notice that none of these questions demand perfection — they’re simply gauges on your ship’s dashboard. They help you see whether you’re sailing in the right direction.
What if the Answer is “No”?
So what if the answer to either question — in the early stages or in a committed relationship — is “No”?
Here’s what we don’t do:
Block them (unless there was violence, abuse, or manipulation).
Send a GIF asking them to delete our number.
Ghost them entirely, leaving them lost at sea.
Instead, we extend what I call The Kind Goodbye. Something like this:
“Thank you for your time and for the conversations we shared and experiences we had. Through reflection and prayer, I don’t feel we are headed toward the relationship I’m intentionally seeking. I pray we each find the person who will best love us as we love them.”
It’s respectful. It’s God-honoring. It follows the greatest commandment — to love God with all your heart, and to love your neighbor as yourself (Matthew 22:37–39).
You cannot control their reaction. You can only control your response.
Common Reaction Scenarios + Christian Responses
- They respond with gratitude.
“Thank you, I appreciate your honesty.”
→ Reply: “I’m grateful for the time we shared and wish you every blessing moving forward.” - They respond with hurt.
“I thought this was going somewhere, I’m really disappointed.”
→ Reply: “I understand this may be painful, and I truly wish you peace and healing as you move forward.” - They respond with anger.
“You led me on! You wasted my time!”
→ Reply: “I’m sorry you feel hurt. That was never my intention. I pray you find the relationship you’re seeking.” - They respond with silence.
→ Reply: None needed. Trust the Lord with the loose ends.
Setting Expectations Early
One way to help avoid confusion is to set expectations up front. Something as simple as:
- “I believe in honest conversations about how things are going. If either of us feels it isn’t the right fit, I’d prefer we say so kindly and clearly.”
- “I’d love to check in after a few dates to talk about what’s been enjoyable and what could be better.”
- “Honesty doesn’t scare me — it builds trust.”
These kinds of “glow and grow” conversations create a culture of openness, so a goodbye — if it comes — doesn’t feel like a shipwreck, but like a natural part of the voyage.
Why Kindness Matters
Because as Christians, our aim is always to leave people better than we found them. A kind goodbye is not weakness — it’s strength under control. It’s love in action. It’s the way of Jesus.
“So then let us pursue what makes for peace and for mutual upbuilding.” – Romans 14:19 (ESV)
When we end with grace, not guilt, we leave the harbor with sails full of peace, knowing we honored God, ourselves, and the person we released.
Breakwater Blessings 
Leave a comment