Do insecurities fade with time?

I was introduced to Sari in 1998 when I had long hair. The first time we met she chopped off my locks and dyed what was left red. My parents weren''t too thrilled. She owns her own hair salon and she''s been cutting my hair for 12 years. Sari was a precursor to actual therapy. 
Dressed always in black. Blond hair one day, purple the next. Sari is that older person that younger people always think is cool: hip style, independent attitude, liberal thinking, easy going, happy, older but still young, and smart. On the weekends, she goes out dancing, grabs drinks with friends or sometimes she''s off for a quick trip to a far off destination to practice her Spanish. She''s in her mid 40''s and always has a sucking candy in her mouth. 
Six Months Ago - We talked about Madrid and what was going on in my life, relationship wise. The difference between Spanish men and American men, e.t.c.
Three Months Ago
- My mom went for a cut and told me Sari had started to see a guy. "Younger," mom said, "But I told her - hey, don''t think too much and go with it."
- I walk in to the salon. It''s a small space with only two pump up chairs. "Just give me one minute, Cyn." She yelled from where she stocks her hair coloring stuff. I sit down and pick up one of the girly magazines - why salons make me want to know about the gossip in the celeb world is truly beyond me. "Sorry, Cyn." She says, chewing then swallowing something. "So, what are you thinking?"
The first question always has to do with my hair. Then I sit, she moves pieces around with her hands, pins parts up to the side, and then rests both hands on each shoulder. "Let''s get you shampooed."
After the mini towel dry I move from one chair to the other. She stands behind me and I see a piece of candy bulging from her taught cheek. She brushes it over her teeth, and parks it on the other side.
"You okay?" I ask.
"He called and broke up with me over the phone." She starts to comb the knots out of my hair. "And you know it was the best four months of dating I''ve ever had. In my forty some odd years of going out - honestly, Cyn, so much fun. So flexible." She moves pieces of my hair to the side and grabs another chunk. "This is the guy I went to Berlin with. Did your mom tell you?"
"She just said you were seeing someone. But, you''re okay?" 
She drops my hair, steps back and looks at me in the mirror. "I''m sad. But, he has some issues he needs to work through." She moves back in and clips my hair up to work the underneath. "Suddenly this rule book came out: He wanted me in by 10 p.m., no more dancing, I was no longer allowed to hang out with my friends, and on it went. I of course told him that wasn''t going to happen. I mean, seriously, what is he talking about - he and I met after 10 p.m. at a club. And out of all the women in the world he could have picked to change and control - oh, no, no, no, honey, I''m too old for that game."
Her fingertips are at the crown of my head, "just look down for me a bit, a bit more. Great.  ... You know it''s like little things, like before he used to hold my hand anytime we were in public, then suddenly it was like he would jump out of the car and start walking before I had even gotten out of the car. And this is when we were on good terms. I was thinking of calling him on his cell phone to ask him if he still wanted to go to dinner." I chuckled. "Seriously, Cyn. I mean if I wanted to go eat alone I would. Then we get back to my apartment and he trips over shoes I''ve left in the hallway. He gets angry. Starts saying how irresponsible I am, inconsiderate, how I need to be a better person and on and on. You know what I said to him? I said, ''You come in and trip over shoes and think - you''re such a child. You can''t even put your shoes away and you get angry. Where as I come in and trip over my shoes and I''m just happy that they''re there, that I have shoes. That''s the difference." She moved to the side. "You know, I don''t want to be a human doing I want to be a human being. Can you lift your head up for me?"
"You know it''s also like the other day he did my laundry. I''m talking loads and loads of it. I had been out of town and I got home from work and he''s there and all my laundry is folded, neatly in stacks around the house. I said thank you, right, because that''s super sweet and then he says, ''well, now you have to put it away.'' Um, Cyn, if anyone knows me at all they know that the last thing I want to do after I come home from work is put laundry away, especially if I could be spending time with people. He told me that was irresponsible. I told him that if I die tomorrow I would rather have been with him tonight than folding friggen laundry. Last night my friends did an intervention." 
Here''s what''s interesting to me about the above scenario. I have yet to meet a woman who is at this stage in the cycle. This is the very beginning stage - where either you recognize what''s happening or you choose to ignore it. I wonder if age plays a role here? Do we understand our self worth more as we age? Sari is in her mid forties. She married when she was younger, and has a child. She is a super self confident woman - and strong enough to defend herself with her words.  
They are no longer together and after a huge telephone fight where she said things like, when did you suddenly switch teams; I''m not the one you should fight against; I should be your safe place - you should be my safe place; when the world is hurtful, we are each others safe place; I want to spend time appreciating and being with you, not fighting you. Sari''s convinced he hates her and never wants to speak to her again. I think him saying he wants nothing to do with her is just a ploy to draw her back in. 
She hands me the mirror and spins me so I can see the back of my head. "The thing is that he has this checklist, which is suddenly all of what I''m not." Sari takes the mirror into her hands. "But, you know, even if I did become all the things he wanted me to be - he would still find some fault. He would then want me to morph into something else."
"Just be careful," I said, taking the smock off. "Because sometimes in these kinds of situations your words and your actions aren''t in sync." 
"Well," she said. "If he went and got help to work through his issues, because they''re his and not ours, I''d wait. It was the most fun I''ve had in forty some years." 
What do people think. Does age help in identifying these kinds of manipulative situations? How many women have found themselves in a similar position - where they see what''s happening while they are inside the relationship and instead of turning a blind eye do something about it.