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Synopsis: Eighteen year old orphan Judy is given the chance of a life-time. Intrigued by her smart-alecky essay poking fun at the orphanage’s ‘blue Monday’ trustees visits, an anonymous trustee decides to give her the chance at a college education for free. Well, with one stipulation: she must write him a letter once a month informing him of her progress in studies during all 4 years of studying, while he remains hidden behind the anonymity of his lawyer. And thus begins the strange relationship between young Judy and her anonymous benefactor.

     I have been thinking about you a great deal this summer; having somebody take an interest in me after all these years, makes me feel as though I had found a sort of family. It seems as though I belonged to somebody now, and it’s a very comfortable sensation. I must say, however, that when I think about you, my imagination has very little to work upon. There are just three things that I know:
     I. You are tall.
     II. You are rich.
     III. You hate girls.
     I suppose I might call you dear Mr. Girl-Hater. Only that’s sort of insulting to me. Or Dear Mr. Rich-Man, but that’s insulting to you, as though money were the only important thing about you. Besides, being rich is such an external quality. Maybe you won’t stay rich all your life; lots of very clever men get smashed up in Wall Street. But at the least you will stay tall all your life! So I’ve decided to call you Dear Daddy-Long-Legs. I hope you won’t mind. It’s just a private pet name – we won’t tell Mrs. Lippett… 

I love Judy’s voice and personality, her quirky sense of humor and plucky spirit. And her voice as a writer: it shines through all four years of college and letters to her ‘Daddy-Long-Legs.” It’s a book that makes me smile every time I re-read it because it’s just such a happy-cheery-adorable little book. The letter-story-telling is pulled off by Jean Webster with delightful ease, inspiring me to put even more thought into my letter-writing, as limited as it might be these days. And the illustrations, absolutely adorable, hilarious and the perfect touch for a book written in such a style.

And one last quote, from our heroine:

I think I might copy that for a reminder on my refrigerator. Time to meet the petty hazards of life with a smile!