Sometimes all it takes is a simple starter to get some good, meaningful conversation going with your student. So, consider asking...
-How is your student enjoying his/her summer activities so far?  Encourage him/her to save a portion of summer job earnings if he/she is working this summer. Talk about how nice it will be to have that money during the fall!
-What did your student enjoy most about this past school year?
-What classes will your student be taking in the fall?
-How is your student thinking about arranging his/her living space on or off campus to make it more fun and effective?
-What activities did your student participate in this past year? What did he/she like the most?
-What goals does your student have for next semester? Talk about things like getting a campus job, academic goals, and applying for a leadership position.
-How can you both be more environmentally conscious?
-Is there a faculty or staff member who really helped or inspired your student this past year? What did he/she do and why?
-How are your student's friends spending the summer?
-What would your student suggest to family or friends going to college this fall?
-What places around campus and Columbia would your student like to explore next year?
-What is your student really looking forward to in the coming year?

These topics not only give you an opportunity to connect with your student, but they also help him or her reflect on experiences gained and goals for the coming semester.