Here's a random list of questions that I've found useful to kick-start conversations:
- What's new?
- How is life?
- How are you and (insert significant other) doing?
- Is anything new with the relationship? Where is it going?
- What are you reading in your Bible?
- What books are you reading?
- What are you doing to make disciples?
- What is God doing in your life?
Lastly, I would just encourage you to be someone who asks genuine questions in an attempt to care for others. Twice this fall I received messages from friends telling me I had been a huge spiritual help and encouragement to them. I think a big part of why they thought that was that I am consistently asking genuine and specific questions of people.
Blessings as you catch-up and encourage friends, both old and new.