What Does 20+ Years of Mentorship Look Like?

Meet Ben & Kyle

Some mentoring stories unfold over a school year. Some last through a season of life. And once in a while, a mentoring relationship becomes something even bigger that stretches across decades.

In 2001, Ben and Kyle were matched through King Street Center’s mentoring program. At the time, neither of them could have predicted what their relationship would become, or how meaningful it would remain more than twenty years later.

But that’s the thing about mentorship — sometimes the smallest consistent moments become the ones a young person carries with them the longest.

How It Started

Like many mentoring matches, Ben and Kyle began by spending time together regularly, meeting weekly for a few years getting ice cream, exploring the waterfront, sharing meals, visiting the library, and working on school projects. They built a foundation rooted in a safe presence, genuine attention, and someone who shows up — what all young people deserve.

There wasn’t a script. There didn’t need to be. It wasn’t about having all the answers. It was just about getting together and doing simple things while Ben listened, encouraged, and made room for Kyle to grow. While Kyle was facing insurmountable obstacles at home, Ben was a steady, positive adult in his life, offering laughter, connection, and helping him just be a kid.

How It Lasted

Life changes. Seasons shift. People move. Schedules fill. And yet, Ben and Kyle stayed connected.

Over the years, their relationship became more intermittent as Kyle came closer to graduation and went off to school while Ben started his family. However, they continued to check-in during major milestones and everyday moments alike. Sometimes it was a big celebration. Sometimes, a quick message for some advice. Mostly, it was simply knowing that the other person is still there.

Their story is a powerful reminder that mentorship doesn’t always look like a straight line. It evolves and continues in different forms.

And in many cases, that steady thread of connection can be exactly what helps a young person feel grounded as they enter and navigate adulthood.

Why This Matters (Especially Right Now)

In a world that moves quickly, where young people are navigating so much pressure, uncertainty, and change, mentorship remains one of the most impactful protective factors we can offer.

A mentor doesn’t have to do something extraordinary to make an extraordinary difference. They just have to show up.

Mentoring can look like:

  • taking a walk and talking about life

  • grabbing hot cocoa

  • playing a game of basketball

  • exploring a new place in the community

  • listening without judgment

  • reminding a young person that they matter

Over time, those moments become more than activities. They become belonging, a confidence builder, a reminder of possibilities.

A Relationship Worth Celebrating

As we celebrate National Mentoring Month, we’re honoring relationships like Ben and Kyle’s, not because they’re rare or “perfect”, but because they reflect what’s possible when a young person experiences consistent care.

Their story is about time, yes. But it’s also about trust and the quiet power of staying connected.

We are deeply grateful to Ben and Kyle for sharing their story, and for reminding our whole community what mentorship can become.

If you’ve been through it, you can be there for it.

Want to be part of this work? King Street Center is always looking for dedicated, caring adults who are ready to invest in a young person’s life.

If you’ve ever wondered whether you have what it takes to be a mentor, here’s the truth: You don’t need to be perfect. You just need to be present.

Learn more and join our mentoring community:

Explore Becoming a Mentor
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A Voice For Vermont Youth