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The first time young miss Belladonna Took tried to follow Gandalf out of the Shire for an adventure, she got as far as Bywater before being taken back to Tuckborough.
She figured what she did wrong was that she should have remembered her manners and asked politely to go with the wizard, instead of stowing away and following him in secret. So the second time, she showed up and asked, polite as you please, if she could pretty please go on an adventure and meet elves and dwarves and men. She had heard such stories of adventure that she decided she would go on one, too.
Gandalf, of course, told her she was much too young to go on adventures, and that she should at least wait until she came of age. This obviously did not suit miss Belladonna Took at all. She was 24! Surely that was old enough for an adventure. The race of men went on some when they were younger than that, after all.
So she waited until Gandalf was a bit of a ways down the road, and, being a few minutes older than she had been last time, followed after him. This time, though, she had to be extra sneaky. If she wasn't caught until far enough out of the Shire, Gandalf would have no choice but to finish out the adventure with her before taking her home. So she set off, sneakily, slightly off the road with some food in a pack, and a pan to cook it with, and a trusty kitchen knife, just in case.
This time Belladonna got even further. She followed Gandalf past the edge of the Shire along the Great East Road and toward Bree. Night soon fell as she followed behind Gandalf, but he just kept going. Weren't you supposed to have a campfire? That's how it always happened in the stories. They would all stop and sit around the campfire and reveal things about themselves and their quest to each other. And how closely they slept was always a direct correlation for how close they were emotionally. But Gandalf didn't stop. Belladonna figured it must be because he didn't know how real adventures were supposed to go, but she couldn't reveal herself just to complain that he's not following the rules of adventure, so she kept following him until they finally got to Bree.
Gandalf went in through the gate, and she tried to slink in before it shut, but she was only half way through when the gate shut on her leg. She couldn't help but make a noise of pain as it slammed into her. That would leave a nasty bruise later. Gandalf and the gatekeeper looked down and finally saw her.
"Well, if it isn't miss Belladonna Took?" Gandalf said and smiled. "To what do I owe the pleasure?"
Belladonna pulled her leg from the now lax gate, straightened out her skirt and said "I have decided I am old enough for an adventure and am taking one with or without you." She then winced a bit. "Though I would prefer to go with you, as I would so love to meet an elf, and you know a great many elves. That is, if you'll have me." She looked up at him with wide eyes.
He looked back down at her and said "You can come. If only because you'll just make more trouble for yourself alone." He turned to look into the town. "Now, you wanted to meet an elf?"