I don't believe you've done a good job of handling the premise. There is a fair chunk of exposition where he explains his life story to whatshername... not to mention the story sounds real. If he's scamming her, it isn't wise to mention being a professional gambler. He should make himself out to be more of a mark... a lucky lottery winner for example.
Written fairly well. Verbose in parts and some exposition poorly delivered.
Watch out for things like 'sits down', you only need 'sits'.