Conversations with College Students During Winter Break
Winter break offers a meaningful chance to reconnect with your college student while giving them the space they need to rest and recharge. Many students come home tired, hungry, and ready for laundry service. They also return with a semester of growth and new experiences they may share at their own pace.
Parents are eager to hear everything, but students often arrive in recovery mode. The line between caring and interrogating can blur quickly. The goal is to create space for conversation without pressure. Think open curiosity rather than rapid questions, and choose moments that feel natural. Car rides, walks, cooking together, shared shows, or late-night snack raids often spark the most honest conversations.
Matt Mayhew recently wrote a great piece in Forbes comparing the college experience to a buffet rather than room service. It is a helpful analogy that can open the door to gentle, reflective questions:
What have you most enjoyed from the college buffet?
What are you planning to put on your plate next semester?
What have you tried that you may not return to for seconds?
My solid go-to question is: What surprised you? You can leave it open or give it more direction:
What surprised you about living in the dorms?
What surprised you about your hardest class?
What surprised you about getting to class?
Studies on college student development show that students communicate most effectively when they feel autonomy and trust in conversations with family.
Ask open-ended questions, listen more than you talk, and let them take the lead. A few thoughtful questions at the right time can help them share insights about their academic, social, and personal growth.
Connection Through Play
Winter break also creates pockets of relaxed time when conversations flow more easily. Introducing an activity that feels low pressure can help spark those moments. The Success Prints Crash Course board game is one way to do that.
The game invites players to explore realistic college scenarios and test strategies for time management, wellbeing, and academics. As students decide how to use their time blocks and see the consequences of their choices, they often talk about how similar decisions played out in real life. The focus stays on the game, which keeps the conversation relaxed rather than evaluative.
This works for both high school and first-year college students. High school players get a preview of how balance and planning shape the college experience. First-year students can reflect on what worked during the fall and what they might adjust in the spring.
While playing, you might ask:
• Does this feel familiar based on your semester?
• What surprised you in this scenario?
• How did you decide which task to prioritize?
• What strategy might you try next time?
The game becomes a shared experience that supports connection and gives insight into how your student thinks about independence, balance, and responsibility.
How to Ask Without Over-Asking
Lead with presence, not pressure. A simple “I have missed you” opens the door without overwhelming them.
Let them talk in spirals. Students jump between stories, classes, people, and places. Follow their thread rather than redirect.
Choose timing wisely. Avoid the moment they walk through the door or when they are exhausted from travel.
Ask questions that spark reflection, humor, or storytelling. Aim for curiosity, not evaluation.
Mix it up. Have a few thoughtful questions ready and a few that are simply fun.
Top 10 Questions to Ask
• What is something you learned about yourself this semester?
• What moment on campus made you laugh the hardest?
• What class surprised you the most and why?
• What part of campus feels most like your spot now?
• What is a small win you are proud of?
• Which class are you looking forward to next semester?
• What is one thing you want to do differently in the spring?
• What has become part of your daily routine that was not before?
• What is one thing you wish you could tell your August self?
• Who has had the biggest impact on you this semester?
Additional Questions
• What campus trend are you fully on board with?
• Which late-night snack saved your semester?
• What was the most chaotic thing that happened in your dorm?
• If your roommate were a season, which would they be and why?
• What is your most-used phrase on campus?
• Who on your floor is most likely to oversleep for an 8 a.m. class?
• What is the most unexpected thing you saw someone carrying across campus?
• If your semester were a movie, what would the title be?
• What is your most unexpected new hobby/activity?
• What is the funniest misunderstanding you have had with a professor, roommate, friend, etc.?
Parent Conversation Starters
• What conversations from class stayed with you this fall?
• How are you managing the balance between academic workload and downtime?
• Which relationships on campus feel most supportive?
• How are you feeling about your major or potential major right now?
• What are you proudest of academically this semester?
• What challenged you the most, and what helped you through it?
• What is one thing you want to try academically or socially next semester?
• What campus resource turned out to be helpful?
• How is your time management evolving?
• What are you looking forward to next semester?
P.S. Find out how Success Prints Crash Course games build college-readiness skills. Explore the game and follow us for more insights on learning through play. Order a copy of the Success Prints Crash Course board game or a license for the Success Prints Crash Course, college simulator, digital game today.