1. What is your relationship with this guy?
2. Do you truly tell him everything?
3. Do you want to be a person that he truly tells everything to?
4. Do you ever feel like he is holding back telling you certain things?
5. Does he ever quickly change the subject when you are talking about serious topics?
6. Are there certain topics that are off limits to talk about with him?
7. Has he shared things with you that he hasn’t shared with anyone else?
8. Does he seem emotionally guarded, or is he typically an open book?
9. How long have you known each other?
10. If he has to make a difficult decision or is conflicted, are you typically the person he turns to for advice and support?