Let’s be honest: bringing up college with your teen can feel like walking through a minefield. One wrong step—too pushy, too soon, too often—and you’re met with a dramatic sigh, a sarcastic “I know,” or the dreaded eye roll.

But here’s the good news: with the right approach, you can talk to your teen about college in a way that invites conversation instead of shutting it down. And May is the perfect time to start. Summer’s around the corner, the school year is winding down, and your soon-to-be senior is just a few months away from application season.

Here are five strategies to help you have productive (and eye-roll-free) college conversations:

1. Pick the Right Moment

Timing matters. Your teen probably doesn’t want to talk about college right after a stressful math test or in the middle of their favorite Netflix show. Look for natural windows—like while driving, walking the dog, or grabbing coffee together—where conversation feels casual and less pressured.

2. Lead with Curiosity, Not Control

Instead of launching into a to-do list, ask open-ended questions that let your teen take the lead:

• “Have any schools caught your eye lately?”
• “What kind of place do you think you’d feel most comfortable—big or small, city or college town?”
• “What are you most excited or nervous about when it comes to college?”

When teens feel like they have a say in the process, they’re more likely to open up.

3. Be the Coach, Not the Quarterback

Remember: it’s their journey. Your job is to guide, encourage, and support—not to take over. Try offering your help with statements like:

• “Would it be helpful if I helped you make a summer plan?”
• “I found a resource that breaks down college costs—want me to send it to you or go over it together?”

When your teen feels like you’re collaborating, not controlling, they’re more likely to listen.

4. Don’t Make Every Conversation About College

It’s tempting to bring up college whenever your teen mentions school, grades, or the future—but constant reminders can turn into background noise. Set boundaries around when you’ll talk about applications or planning (e.g., “Let’s chat Sunday evenings for 30 minutes”), and give your teen space to breathe.

You want them to feel supported, not surrounded.

5. Acknowledge the Stress

College planning can feel overwhelming—even for the most motivated student. A little empathy goes a long way.

Try: “I know this stuff can feel like a lot. We’ll take it one step at a time.”

Even the most confident teen needs reassurance that they don’t have to figure it all out right now.

Final Thoughts

The college application process is a big deal, but it doesn’t have to be a constant battle. By approaching the topic with patience, respect, and a healthy dose of humor, you’ll not only get further—you’ll strengthen your relationship along the way.

Eye rolls may still happen. But they won’t be the only thing happening.

Want more tips like this? Download our free College Prep Checklist for Parents of Rising Seniors and stay ahead of the curve—without the drama.