Bilbo put a letter on the spoons to Angelica so they were for her
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He lost his reputation because he was no longer a normal hobbit; now he was adventurous.
Bilbo Baggins' Diary Entry Dear diary, Today, after having thirteen unexpected guests over at my house I was taken on an adventure. I was only just starting to realize how far this journey would be and how much respect I would lose from my community when we were faced with three nasty trolls. Their names were Bert, Tom and William. They were complete morons. They were also very hungry and thought the dwarves would be perfect for dinner. Thankfully, they had no interest in eating me. Just as the first of the dwarves was about to be cooked, Gandalf made his move. Like me he had noticed that the trolls were not very smart. So when they were not looking he sneaked into the bushes behind them. Then he started teasing them but did it in a way that made the trolls think it was them. Once they were confused and had started fighting with each other, I slipped on my invisibility ring and set the dwarves free. After that Gandalf turned the trolls into stone and we had a lovely dinner. Although it was delicious, it was not a good start to our quest.
As the dwarves and Bilbo were traveling through Mirkwood, they began to lose hope. It was dark, damp, and nearly pitchblack. There was no sunlight, no breeze, and the air was clammy and moist. They didn't have any decent food left, nor water, and they used up their arrows most foolishly. It was miserable. I don't blame them for getting so upset.
After Gandolf has left and they think they will be lost in Mirk wood forever
They are both hobbits, or at least Gollum was closely related. They were both used by the ring. They both lose a bit of their souls to the ring. And the ring gives them both unusual longevity. Gollum and Bilbo also appear to speak a similar dialect, or at least know the same language enough to communicate.
Bilbo uses his magic ring and his wits. He follows Gollum with the ring on and is able to leap over him to get to the back door. There he squeezes through, though he lose his buttons doing so.