What does it feel like? Psychologically. Physically. Etc.
When have you been lonely?
Difference between loneliness and being alone. (You can be alone and content or in a crowd and lonely.)
What are some things you do to avoid being lonely?
How do you enjoy spending time alone?
How does being single affect your happiness? Is it a positive? Negative? Back and forth?
Do you feel pressure to find a relationship? Where does that come from?
What is your philosophy for “the hunt”?
Online vs offline
Having a “type” or checklist or list of deal-breakers
“Friend zone” vs romantic possibility
Experiences with moving from friends to romantic and the other way around
What are some of our expectations during dates? Getting to X-base by the Yth date, good night kiss, etc. Are these expectations assumed based on the context of the date (for example, lunch date is casual, doesn’t mean anything… evening date means you should at least kiss, etc)
Balancing one-on-one with a sig other vs time alone or with other friends
Having feelings but having to separate for other reasons - employment, move, etc.
Why do we marry? Why do you think less people are getting married now-a-days?
What are your thoughts on living together before marriage?
Love over time - How do we grow/adapt together?
Falling out of love?
What are your thoughts about divorce? Personal experiences?