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Hi Meg,
Your friend, how you describe her, is definitely showing signs of depression/low self esteem/mental health issues. She needs expert help to deal with this. It doesn’t sound as if she is going to take any advice from you. You could invite her out for coffee/lunch and see how that goes but ultimately you may have to call time on this friendship at least until she has dealt with some of her issues. (Depressed people frequently want to shut the outside world out so she may not be receptive to this.)
You may have to accept that your life has taken you in different directions, you are not 16 any more and you don’t have the same connection.
Peggy