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After the narrator describes the various pilgrims who have assembled to make the pilgrimage to Canterbury, he describes the Host and what a jolly, well-natured individual he is. He seems to be the perfect host, encouraging all of his guests to eat and drink well, and is able to encourage them all to join in the general merriment. Note what he says to the group of pilgrims who are with him:
You are all welcome here, and heartily:
For by my truth, and telling you no lie,
I have not seen, this year, a company
Here in this inn, fitter for sport than now.
Fain would I make you happy, knew I how.
And of a game have I this moment thought
To give you joy, and it shall cost you naught.
The Host is therefore able to gain the trust of the pilgrims through first and foremost his generosity and his pleasant nature. Note how in the quotation he flatters the pilgrims, telling them that they are better than the other pilgrims he has seen in previous years, as they are "fitter for sport" than they were previously. He also has the desire to make them happy, and has constructed a game in order for this to occur. The Host wins the confidence of the pilgrims therefore through his actions and his speech. He is clearly a very good host, as his name suggests, and what he is able to do is to unite a very disparate group of pilgrims around a common purpose: the storytelling competition.
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