Ughhh... remember when I dated Bobby?!¹

I was chatting with my mentor recently about a guy I used to date—you know, one of those “What was I thinking?!” relationships—and half-jokingly asked, “So why did you let me date him for that long?”

Little did I know, this was about to be a full-on Mentorship 101 moment. *Cue the heavenly spotlight and faint harp music.*

She calmly replied, "I knew he wasn't the one, but that was for you to discover—not for me to tell you. That's part of learning God's still, small voice." I'm pretty sure I internally eye-rolled. I mean, aren't mentors supposed to tell us what to do to protect us from ourselves?! (Spoileralert: the answer is no. Keep reading...)

At first, I felt a little frustrated. I was like, "Scuse' me ma'am but I was struggling. A little red flag flair would’ve been appreciated." Why didn’t she just save me the time, drama, and heartache by telling me the truth outright? But then I had to ask—would I even have listened? Or would I have stayed stuck in a mediocre relationship simply to avoid the discomfort of letting go and trusting God's best for me?

Looking back, I realize she never pressured me. She didn’t bash him or give me a checklist of red flags. Instead, she listened, asked thoughtful questions, and stayed curious. If I asked directly, she would be honest—but always in a gentle, prayer-centered way. For example:

Me: "So...what do you think of him!?"

Mentor: "Well, he's a kind guy. He loves Jesus. He treats you well. I am a little concerned you don't sound more excited about him, though. What do you feel like God is telling you? What is your gut saying?"

Never once did she say, "You need to break things off. He's not right for you and God's already made that clear to me—and you know it too!"

Because the truth is, deep down—I did know. And I’m pretty sure God was waving red flags like he was landing a plane—but I still needed to arrive at the gate myself. I had to come to that realization on my own. I needed to wrestle with the tension between my emotions and God’s voice. I needed to recognize when my feelings were out of alignment with His will.

Meanwhile, my mentor had to trust God with me as her mentee. “I prayed for you constantly," she said. "I asked God to speak to your heart, to give you wisdom and clarity, and to make the next step obvious—when the time was right.”

By the way, this lesson isn't just for dating. It could apply to a toxic friendship, a job you’re scared to leave, or a loan you shouldn’t take out. Sometimes we don’t move because we don’t have clarity. Sometimes it’s fear. And sometimes… it’s just laziness. Thank God He sees our hearts and is always teaching His children (of all ages) to carry His yoke, for His yoke is easy and His burden is light (Matthew 11:30).

This is one of the most valuable parts of a mentoring relationship:

• For mentees – learning how to pause, pray, and invite the Holy Spirit into our decisions rather than relying on impulse or emotion.
• For mentors – learning to release control, resist the urge to “fix,” and believe in the power of prayer and godly counsel.

“The purposes of a person’s heart are deep waters, but one who has insight draws them out.” Proverbs 20:5 (NIV)

“When the Spirit of truth comes, he will guide you into all the truth...” John 16:13 (ESV)

This is why we mentor.

¹Name changed for privacy. I doubt "Bobby" is on my email list, but hey, you never know.

My More Precious Than Pearls curriculum is all about helping young women grow in wisdom, discernment, and godly decision-making—just like the story I shared.

📘Check it out: www.prayherforward.com