I don't necessarily think he's crossed any boundaries, but he seems inexperienced. I do think you should think about whether you co tinue to see him based on how you feel and if you continue to feel confusion about the dynamics between the two of you. I agree that this awkawardness of what to/ what not to say is common for male/female pairings in therapy, especially if the therapist is new. I think Ts begin to develop their boundaries over time as they gain experience dealing with a variety of personalities. Your therapist hasnt had that yet, so he probably doesn't know how language and other seemingly benign things you'd say to a friend you wouldn't say to a patient. It could be good for him to learn from you, but only so long as the relationship is helpful to you. If his kindness is something you're not used to, it could be difficult for you to deal with without making more out of it. I had a similar dynamic when I first began seeing my psychiatrist a few years ago. He is handsome charming and all that. He had a lot of experience in research and hospital settings, but private practice was new to him. So he has changed a bit from when I first met him. Some of the things he'd say would leave me scratching my head, and I wondered if I liked going to him a little too much. But over time that faded and I've been able to be completely genuine with him. We are a lot alike and would get along well in a different setting, but that's not going to happen. So, I've learned to use my interactions with him to help me relate to men in different ways. Most notably that you can be friendly, get along, feel attracted, work together yet not worry about being judged or worry about sexualizing the relationship. Thats what Ive gotten out of it at least and its helped me deal with my fear of men.