Took many years to cry in therapy. I have been in therapy for 25 years on and off. It took me a lot of time to trust therapists. With my last therapist I was able to start getting to the core of issues and was able to start feeling. With my current therapist I cry when I need to. I remember the sessions where I always felt like I was crying though. It took me even longer to cry in group therapy. I had learned to turn off my feelings and to cry alone. I had to unlearn that and learn to trust.