A seemingly well adjusted 29 year old film maker is forced to face his own insecurities when forced to produce a movie on teenage female self esteem

As the others have said and Richiev's suggested logline connects in a nice ironical way to the subject of the documentary.

If possible you should try for a more proactive lead character in the logline.
??
While making a documentary about teenage self esteem, a seemingly stable filmmaker is inspired to ask out his high school crush who he was too insecure to approach in High School.?
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Obviously your logline will be different, however I believe the lead; instead of ?forced to face his insecurities? should be ?inspired to act?? (Do this thing that once scared him)
Good luck, hope that helped.

I don't mind the 'seemingly well adjusted' bit; it tells us that his beliefs are about to be challenged. But I agree there should be a particular young woman who challenges his beliefs. And, yes, have him producing a film, not being forced to produce one. He thought he had solid views on the topic, but he in fact has something to learn.