According to Theory of Mind, Individuals with Asperger's are poor at inferring what others are thinking and feeling. As a result, they may come across as rude or uncaring since they aren't tuning in to where a speaking partner is "coming from." Regardless of whether someone "has" AS or not, this is a helpful guiding principle and leads us to ways to help these folks "tune in" more effectively. One helpful hint is to have the AS/poor Theory of Mind type ask questions in conversations: "What are you trying to say?" "Can you tell me more about what you are thinking?" AS individuals need to learn to collect more information in an explicit way.
In terms of dating, the same method is helpful. The AS person needs to ask relevant questions of the person whom they are interested in: "Do you have a boyfriend?" "Would it be ok if I asked you out?" and so on.