Apart from having a job and family, what else would you like to have in common with your T? If it was easy for you to get a job, relationships, etc., then you might not be seeing T in the first place. So, what is it? Hobbies? Favorite books? I don't mean to sound dismissive or judgmental; forgive me if that's the way I am coming across. But, even if you had hobbies in common, you wouldn't be doing those hobbies together, because she is still your T. It's not like you could go shopping together for hobby supplies, you know? Based on my own experience, and this is only my opinion, I think you are looking for ways to connect more to your T, because when you are feeling depressed, you would like a feeling of a stronger connection/attachment to your T. If you had a job and family, as T does, you might still be wanting that stronger connection. Sure, it could be some envy or jealousy of something T appears to have that you don't, but it could be that T wishes (sometimes) she was single, so she could do whatever she wanted, whenever she wanted, without so much responsibility placed on her. I'm sorry that your first session after your break was so hard. Even though it hurts, I encourage you to tell T exactly how you felt (about her, about yourself) during the break. And let those tears fall. They aren't doing you any good staying in your head.