EXTENDED SUMMARY:

Gandalf is in an awfully bad mood when he arrives at Bilbo Baggin's house, only to find that the once adventurous young Hobbit is now a respectful (read: boring) gentlehobbit. But what if their meeting didn't occur like that?

Gandalf tried to visit Bilbo earlier in the year, but Bilbo was not home. ("Gandalf came to the Shire to visit him in T.A. 2941 but [Bilbo] had disappeared again [on one of his walks] because of Elven new year" ( /wiki/Bilbo))

Holman Greenhand, Bilbo's current gardener, (pre-Hamfast Gamgee, see /wiki/Holman_Greenhand), tells Gandalf where Bilbo went on his walk instead of describing him. Thus, Gandalf meets with Bilbo on Yestarë, the Elven New Year, the first day of spring and the renewal of nature. Point being, their meeting is much more pleasant and much earlier. This changes things. (A lot of things.)

OR

An AU wherein their earlier meeting sets off a chain of events that changes the fate of Middle-Earth.

"While there's life there's hope."

—Bilbo, quoting Bungo, his father, when the company loses hope at the entrance to the Lonely Mountains.

Holman Greenhand was a master gardener, renowned throughout the Shire for his green thumb. He cared for not only his own garden, but also the gardens of several of the best-off hobbits in Hobbiton. Young though he was, Holman knew his craft well. He had been born and raised a gardener and had spent his whole childhood learning every secret of the plants he loved.

His very favorite garden was that of Mr. Bilbo Baggins, a gentlehobbit who lived in his family smial, Bag-End, on Bagshot Row. Mr. Bungo Baggins, his previous master, gave him free reign over the garden when he hired Holman as he was much more of a builder than a gardener.

When young Mr. Baggins grew up, it became clear that he loved to garden, but he kept Holman on as a gardener anyways. He was only two years older than Holman and thus the two became good friends. Often the two were seen together, drinking tea and chatting or elbow-deep in fresh soil. Together, the two cultivated the biggest tomatoes and the most beautiful roses in all of Hobbiton, and probably beyond besides.

Holman was 49 when he changed the fate of the known world, and in a very poor mood besides. The day was Yestarë, the Elven new year, and Mr. Baggins was off adventuring again on one of his walks. Mr. Baggins was what many in the Shire would call odd — he liked going on long walks, telling and hearing tales of adventures, and getting into all sorts of trouble.

As fauntlings, Mr. Baggins had been much worse. It was only after the death of his mother, Mrs. Belladonna Baggins, that he had begun to settle down and only, many gossiped, enough to take care of his new responsibilities as Master of Bag-End. He still walked long and far, visiting nearby groups of traveling Elves and Men or exploring the edge of the forests. Some even spoke of seeing him down by the riverbed walking, a place no respectable hobbit would be caught anywhere near for fear of drowning.

Of course, Holman knew Mr. Baggins had no such fears. Mrs. Belladonna had taught them both to swim years ago, despite the aggrieved protest of Holman that it was very unhobbit-like. Indeed, the river was exactly, Holman knew, where one could find Mr. Baggins that night.

He told Gandalf as much when he came by to visit. It would do Mr. Baggins good, Holman knew, to see his mother's old friend. Holman could see what the Shire's gossiping was doing to poor Mr. Baggins. It was killing his spirit, all the talk of "being respectable" was, and there was no mistake about it.

"Perhaps," he told Gandalf that night, "you can help him, for I see no way for me to do anything about it. Much more of this teasing, tormenting, pressuring — whatever you want to call it — and he will be ruined, just ruined, I'm telling you, for anything but sitting around and complaining."

Gandalf gave Holman a very strange look at this remark.

"Indeed?" he said, raising one of his Very Intimidating eyebrows, "And is that not what a respectable hobbit does? Do you not think he should be one?"

Holman flushed.

"An entirely respectable hobbit Mr. Baggins may not ever be, but I like him that way. He is my friend, and I know that if he becomes anything but odd he would not be himself, or the friend I've grown to love these past four decades. Please, Mr. Gandalf, you must do something!"

Gandalf nodded.

"I cannot promise you anything, Mr. Greenhand, beyond that I will try to help. However, try I will," and here Gandalf paused to crouch next to Holman. "In fact, I think I have the perfect adventure in mind to help our dear Bilbo regain his former self. Don't you worry; I'll see to it that Mr. Baggins never loses that adventurous side of his. This will be a great opportunity for self-discovery. Or," and by this point, he had stood up and was wandering down the path towards the river, mumbling to himself, "or is it rediscovery? Re-self-discovery? Oh confound it all..."

***A/N: I did quite a bit of research for this fic, online and from the original novels. I've also seen both Hobbit movies a few times. My head canon is a mix of the three sources, plus my own imagination. If you'd like to know which parts came from which source, just ask. Warning: This is a WIP. My goal is to keep to weekly updates. I may not succeed.