How do I know if my ex-girlfriend deserves another chance? We broke up a few months ago and I didn’t speak to her for a while because I was angry but, as time passed, we have begun to chat again. She says she has realised that she did a lot of things she shouldn’t have and has apologised because she takes responsibility for the failure of our relationship. I am happy that she has done this but am also in pain because her actions made my life very difficult. I still love her but the memories of what occurred prevent me from agreeing to try this again. Should I listen to her?
You have to decide if your feelings override what you want from a relationship, and if her presence in your life matters. If it does, the best way to see if this can work is by taking it one step at a time and gauging her by her actions rather than by words alone. It’s important to talk about what went wrong, but it’s also important to acknowledge your own role and ask questions about what you could have done better. Blaming one person for the failure of a relationship isn’t a good way of trying to make it work a second time. Have more conversations about what you both want, be honest about your intentions, and don’t commit until you are both comfortable with the idea.

There is a 12-year difference between me and a guy I have been dating. I like him a lot, but this fact prevents me from telling him how I feel. How will I know if this has a chance of working out?
Any relationship can fail if both partners don’t commit to making it work. A difference in age shouldn’t matter if the important things like love, mutual respect, trust, and honest communication exist. Tell him how you feel and ask for his perspective. Also, remember that you have the option of ending this if it doesn’t work out.