wikiHow Conversation Starters for Difficult Conversations Here are 20 conversation starters for a difficult conversation: 1. "I need to talk to you about something important." 2. "Can we set aside some time to have a discussion?" 3. "I have some concerns I'd like to discuss with you." 4. "I'm feeling frustrated/disappointed/concerned and I need to address it." 5. "I think it's important that we have an open and honest conversation." 6. "I need to bring up a sensitive subject." 7. "Can we discuss something that has been bothering me?" 8. "I think we need to have a conversation about our relationship/friendship." 9. "I need to talk to you about your behavior." 10. "I think we need to address some issues in our communication." 11. "I need to discuss something that affects both of us." 12. "I think it's important for us to have a clear understanding of each other's expectations." 13. "Can we talk about what's not working in our relationship/friendship?" 14. "I need to express my feelings about a specific situation." 15. "I think it's important that we have a discussion about our goals and priorities." 16. "I need to talk to you about a decision I've made." 17. "I think it's time for us to have a difficult but necessary conversation." 18. "I need to address a problem that has been affecting our relationship/friendship." 19. "I think it's important that we work through this issue together." 20. "Can we talk about what we can do to improve our relationship/friendship?" Page