I was wondering if it is okay to do tawassul to the same person every time if I feel more connected to that person. For example if I feel more connceted to Imam Ali (as) or Imam Hassan (as) is it okay for me to do tawassul to him everytime, or should I then also times do tawassul to others for example the Prophet, or Imam Mehdi even if I feel more connected to another one?

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It is ok, but it it’s recommended to seek the Shafa’a and Tawassul of other members of Ahlulbayt (a).