I think I understand where you are coming from O.P. But please don't judge until you know this woman's background.
I was abused as a child. Later, my parents split up in my adolescent years. I had a mother who loved us, but only put food on the table and clothes in our wardrobes. We were never pushed, or given much aspiration. I failed everything in school due to PTSD.
I had no 'life plan' I had no idea of the possibilities in the world. I met a guy who showed me kindness and understanding for the first time in my life. We got together briefly. I got pregnant. I was 20. I chose to keep the baby. I worked for a few years earning about £50 more than if I had stayed on the dole.
At play groups, I met middle-class yummy mummies with attitudes like yours. They didn't see me, all they saw was a young un-married girl, with no money and no friends. They more or less shunned me. They believed I had 'chosen' to be poor and unmarried, which I guess I had, but in what way did I 'choose' it O.P.?
You see YOU CAN ONLY CHOOSE AMONG THE OPTIONS YOU MENTALLY BELIEVE ARE ATTAINABLE AND ACTUALLY AVAILABLE TO YOU. If you cannot see option C due to how you have been brought up etc., then you only choose between option A or B. IFYSWIM.
That was where my life was then. I had 0 confidence and truly believed I had 0 options.
I do think society is letting people down, particularly young women. I do agree it is sad that this woman hasn't aspired to more in her life. I do feel angry that we seem to accept this without question. However, I know what it feels like to be judged by people who are lucky enough to have started life further down the race track.
So be angry but try hard to see what's behind this woman's attitude. And yes, have some compassion. You don't know where she's coming from.