I hear you and have had the same experience in relation to rejecting great guys by pulling no shows or cancelling. All this does is make them feel rejected and made me feel angry at myself and even more rejected by them for not chasing. Its hard but can you try to take this a little slower? If it's a first date remember, so love isn't even a part of it yet. You are just meeting for coffee or drinks. Try staying in the moment and keeping your focus. Everyone has relationships that didn't work out on the past with various people, including their Ts, no one is immune to that. It sounds like you do have the upper hand here since it sounds like he likes you a lot. This is a date so it's not even in the same ballpark as your relationship with your T. I know you are aware of this but maybe if you can think about it in terms of male/female dating dynamics rather than female/female therapy/friendship dynamics it will help you keep some perspective. The two are very, very different. If you push him away it will hurt his feelings and your chances at a good experience. Try not to let your ex T have that kind of power over you and your life.