You call your freshman and ask:

“How’s everything going?”

“Good.”

“How are your classes?”

“Fine.”

“Are you making friends?”

“Yeah.”

And that’s about all you’re getting.

A month into college, many parents are starting to relax. Their freshman survived move-in, found their classes, figured out the dining hall and seems to be settling in.

But here’s the thing:

“Fine” doesn’t always tell you very much.

Your freshman may genuinely be doing great.

Or they may be struggling with a class, feeling lonely, spending too much money, staying up until 3 a.m. or wondering why everyone else seems to be adjusting better than they are.

The goal isn’t to interrogate them or search for problems that aren’t there.

It’s to create opportunities for a real conversation.

Instead of repeatedly asking, “How’s college?”, try asking better questions.

Here are 7 questions parents should ask after the first month.

1. “Which class feels the hardest right now?”

This is much more useful than asking, “How are your classes?”

By now, your freshman has probably had quizzes, assignments and possibly their first exam.

They should be starting to understand which classes will require more work.

If they mention a difficult class, resist immediately telling them what to do.

Instead ask:

“What do you think would help?”

Maybe it’s office hours.

Maybe it’s tutoring.

Maybe it’s forming a study group.

Maybe it’s simply starting assignments earlier.

College students need to learn that asking for academic help before they’re failing is a strength, not a weakness.

2. “Who have you been spending time with?”

Notice the question isn’t:

“Have you made friends yet?”

That can make a lonely freshman feel as though they’re already behind.

Friendships take time.

Instead, ask who they’ve been eating with, studying with, sitting next to in class or hanging out with on weekends.

Your freshman doesn’t need a huge friend group after one month.

You’re looking for signs that they’re beginning to make connections.

Maybe they haven’t found their best friends yet—and that’s completely normal.

3. “What does a normal weekday look like for you?”

This question can tell you a lot without asking 10 separate questions.

What time are they waking up?

Are they actually going to class?

When are they studying?

Are they eating regular meals?

Are they exercising?

Are they staying up until 3 a.m. every night?

College gives students an enormous amount of freedom—and very little supervision.

One of the biggest challenges freshman year is learning how to create structure when nobody else is creating it for you.

You don’t need to manage their schedule.

But you do want to know whether they’re beginning to manage it themselves.

4. “How’s your money lasting?”

A month into college is the perfect time for a financial reality check.

Those little expenses add up quickly:

Coffee.

Food delivery.

Uber.

Target runs.

Going out.

Online shopping.

Late-night food.

Your freshman may suddenly realize the spending money that was supposed to last until Thanksgiving isn’t going to make it through September.

Don’t wait until the account hits zero.

Talk about it now.

If they’ve overspent, resist immediately replenishing the account without a conversation.

Ask:

“What do you think you need to change?”

Learning to budget is another part of learning to live independently.

5. “What’s been the hardest part of college so far?”

This may be the most important question on the list.

And then?

Listen.

Don’t immediately fix it.

Don’t minimize it.

Don’t compare their experience to yours.

And don’t panic if the answer isn’t what you hoped to hear.

Maybe they’re homesick.

Maybe their roommate is driving them crazy.

Maybe they haven’t found their group.

Maybe they’re overwhelmed academically.

Maybe they’re surprised by how much they miss home.

You don’t have to solve every uncomfortable feeling.

Sometimes your freshman simply needs a safe place to say:

“This is harder than I thought it would be.”

6. “What’s been better than you expected?”

Don’t make every conversation about potential problems.

Ask about the good stuff, too.

Maybe they love one professor.

Maybe they discovered a club.

Maybe they finally found someone they really connect with.

Maybe they love having more independence.

Maybe there’s a class that’s completely different from anything they took in high school.

This question helps your freshman—and you—notice the progress that’s easy to overlook.

College adjustment isn’t necessarily:

“I hated it, and now I love it.”

Often it’s:

“Yesterday was hard, but today was actually pretty good.”

Those good moments matter.

7. “What are you looking forward to?”

This is one of my favorite questions because it shifts the conversation toward what’s ahead.

Maybe they’re excited about:

A football game.

Parents Weekend.

A club event.

A concert.

Going out with new friends.

A trip home.

A class project.

Their birthday.

Even something small counts.

Having something to look forward to can be a sign that your freshman is beginning to build a life on campus.

And if they can’t think of anything?

That doesn’t automatically mean something is wrong—but it may be worth continuing the conversation.

Parents: Don’t Ask All 7 Questions at Once

Please don’t call your freshman tonight and say:

“I have seven questions for you.” 😂

This isn’t an interview.

Spread them out.

Ask one while you’re driving.

Bring another up during FaceTime.

Let the conversation happen naturally.

And remember that your freshman may talk more when you’re not trying so hard to make them talk.

Sometimes the best conversations start with one good question followed by enough silence for them to actually answer it.

What Should Parents Be Listening For?

Don’t judge your freshman’s adjustment based on whether everything is perfect.

It won’t be.

Instead, look at the overall picture.

Are they:

Going to class?

Eating and sleeping reasonably well?

Beginning to make connections?

Handling their responsibilities?

Learning from mistakes?

Having at least some good moments?

Starting to solve problems without immediately calling you?

If the answer is mostly yes, they’re probably doing exactly what freshmen are supposed to be doing:

Figuring it out.

But if you’re hearing about persistent isolation, frequently missing class, significant changes in eating or sleeping, heavy substance use, overwhelming anxiety, hopelessness or an inability to function day-to-day, don’t dismiss it as normal freshman adjustment.

Encourage your student to connect with campus counseling, student health services, an RA, academic advisor or another trusted adult on campus.

And any talk about self-harm, suicide or not wanting to be alive should always be taken seriously and addressed immediately.

The College Ready Bottom Line

After the first month, parents naturally want reassurance that their freshman is okay.

But you’re probably not going to get the whole story by asking:

“How’s college?”

Ask questions that open doors.

Then listen.

Your job isn’t to monitor every grade, friendship, meal or decision.

And it isn’t to make sure your freshman never struggles.

Your job is gradually changing from manager to sounding board.

You’re still there.

You’re still their parent.

You’re still one of the people they trust most.

But now you’re helping them develop the confidence to say:

“This is hard—but I think I know what to do next.”

And that may be one of the most important signs that your freshman really is doing fine.

College Ready

Helping parents guide their students through the transition to college—and helping students learn to navigate it on their own.