Me, Natalie (1969)

James Farentino plays artist David Harris

Me, Natalie on IMDB

'From childhood, Brooklyn teenager Natalie Miller, with upper front teeth that are slightly bucked and a nose too large for her face, has considered herself homely, and she never has subscribed to her mother's determined belief that she will grow up to be pretty. Her father, a druggist who doesn't share his wife's optimistic outlook, bribes myopic optometrist Morris to marry her, hoping his nearsightedness will prevent him from seeing she's no beauty.

After she discovers her father's plan, Natalie leaves home and moves to Greenwich Village, where she rents an apartment from eccentric Miss Dennison and sets out to enjoy a Bohemian lifestyle. She finds employment as a cocktail waitress at the Topless Bottom Club and befriends drug-addicted go-go dancer Shirley Norton. Although she contemplates suicide after discovering her aspiring artist lover David Harris is married, he finally convinces her she's a worthwhile human being and not the ugly duckling she imagines herself to be.'
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