Initially:
* Skeptical: Gandalf initially sees Bilbo as a "comfortable hobbit" with little adventure in him. He views Bilbo as a surprising choice for the quest, but also sees potential in him.
* Intrigued: Gandalf is intrigued by Bilbo's adventurous spirit and his ability to surprise, shown by his bravery in the Troll Cave and his unexpected skills in "burglary."
* Respectful: Gandalf recognizes Bilbo's courage and resourcefulness, even when he doubts himself. He acknowledges Bilbo's strengths and his contribution to the company's success.
As the story progresses:
* Appreciative: Gandalf becomes increasingly appreciative of Bilbo's character. He sees him as a key player in the success of the quest, a valuable member of the company, and a true friend.
* Proud: Gandalf is proud of Bilbo's growth and development as a hobbit. He admires his courage, his resourcefulness, and his willingness to step outside of his comfort zone.
* Concerned: Gandalf also expresses concern for Bilbo's well-being, especially during moments of danger and hardship. He is aware of the toll the journey takes on him, both physically and emotionally.
Ultimately:
* Affectionate: By the end of The Lord of the Rings, Gandalf has grown fond of Bilbo. He sees him as a dear friend and respects him greatly for his contributions to the greater good. He also understands the burden of the Ring on Bilbo and is sympathetic to his struggles.
In summary, Gandalf's feelings toward Bilbo evolve from initial skepticism to deep respect, appreciation, and affection. He sees Bilbo's potential, celebrates his successes, and is genuinely concerned for his well-being throughout their adventures.