Hi Jenn1fer82 - it sounds as though your date is struggling to overcome some complicated feelings he still harbors towards his ex. It wasn't exactly an oppertune time to discuss the matter but perhaps he was trying, in an albeit direct way, to learn more about you and what you feel about the situation. I personally think he should have kept some of these thoughts to himself - as shezbut said, it makes him appear resentful and still very much involved with the past. You are not the person he should be working this through with and whilst im sure you will be there to support him to a degree i think its unfair of him to put so much emphasis on his ex whilst at the same time asking you to commit to a relationship with him. It could be argued that maybe he isn't quite over the whole situation and needs to take some time to work on himself before he enters another relationship. I would state outright to him that you're sorry for what happened between him and his previous girlfriend but that you've got all the details you need and instead want to focus on you and him. If that doesn't give him the hint its unlikely anything else will...