A lot of others have made good comments about making this about how YOU feel, not how your mom feels, but I did want to point out that harping on T's childlessness is really just another distraction from your own feelings. If I had to guess, what's going is that you feel really guilty about feeling anything negative about your mom, and this is a way to transfer that onto your T. I don't want to dwell on this point because it's personally extremely triggering for me right now, but I do think you know deep down that it's not a terribly good excuse to brush aside your T's concern about negative feelings you may have had around your mom. The concern, as it should be, is about you -- not your mom, not your T, and not your T's nonexistent kids.

This has been hard for me, too, and it's taken a long time for me to see that there's a difference between acknowledging hurtful things my mom has done and saying that she did something wrong or was a bad mother. My mom did plenty of things wrong, and some of those really hurt. My mom also did plenty of things right, and some of those hurt too. The point of therapy is to talk about my experience, and how all of that stuff shaped me. My therapist is male and 20 years younger than my mom, and I don't think that makes him less capable of working through those issues with me.

I don't blame your mom for saying "I used to be so proud of you." Putting myself in her shoes, I don't know, it might have come out of my mouth too. But I will say that when I read it, I was identifying with you at the time, and it hurt to read. I probably frowned visibly. And if it were me, I'd have been very upset. That's kind of the point -- her disappointment in you was meant to be palpable. If she just made you feel good about everything, she wouldn't be doing her job.