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I like this guy but i do not know how to tell him he some times is a pest can you help me. I think you should break up with him and wait a few weeks before expecting him to get used to the idea of you dating his friend.
Hookers in Dorsey - Are you sure you want to delete this answer. Going on dates usually means that 2 people like each other or are trying to see if they like each other. Yes, the guy should pay for the 2 of them.
Then you can tell her that you like her, and see how she reacts.