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

Hi Matt.

Was this double post a mistake? Or intentional?

If possible you should try for a more proactive lead character in the logline.
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"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.