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When a person (typically a guy) goes out to see a movie, or visits a theme park, or place [otherwise] mostly occupied by couples or friends,but does this alone. This can cause sympathy from other people that watch them as they purchase tickets or enter the area. This is different from when a person grabs a cup of coffee, or sits in a [coffee shop] alone for a few minutes, or rents a movie, or eats fast food. Masterdating involves often going to a restaurant alone, and sitting at the table alone, while some people look and either feel bad, or think that the person is a looser, or going to see a movie alone. It is often done by older men that may be widowed, or by people that can't get a [girlfriend], or are the "40 year old virgin" type
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