1. Do you think that person regrets letting you go the first time?
2. Do you see tangible changes in their behavior in general?
3. Do you see tangible changes in their behavior with you?
4. What are their friends saying about them now?
5. Do you think you can start over without looking back?
6. Are you willing to put the past behind and act like you’re just getting to know that person?
7. Did you get closure the first time or do you still need one?
8. What’s the worst that can happen if you give them a second chance?
9. Do you feel like your life is better or worse without that person?
10. Do you think this person can add value or meaning to your life?
11. Do you think you will be able to let go if things don’t work out again?
12. Do you have certain expectations you don’t think this person can meet?
13. What’s the main reason that’s stopping you from trying?
14. Are you willing to trust this person again like you used to?
15. Are you willing to do your part in making it work or do you expect the other person to do all the work?
16. How will this person fit into your new lifestyle?
17. Is the person aware of how much you’ve changed as well?
18. Are you seeing changes in actions or just in words?
19. Do you think they have a tendency to take you for granted again?
20. Do you feel that they’re sorry even if they don’t say it out loud?
21. Do you know why they suddenly changed?
22. Was their approach genuine or manipulative?
23. What are your friends telling you?
24. What is your gut telling you?
25. Did fate play a part in reconnecting you with this person?
26. Has this person given you a second chance before?
27. If the tables were turned, how do you think this person would react?
28. Do you think you will regret not giving this person a second chance?
29. Do you think you could afford to lose them again?
30. Would you rather live with them or without them?