Istikhara in the Shi'i tradition answers the question of "what should I do?", not "what will happen?" It is useful if you have a clear choice in front of you ("should/shouldn't I do this?") and the ability to act on that choice.
From your question, it sounds like you currently do not have the choice to marry or not-marry him. That is, the matter is not in your hands. Therefore, if the question was just, "Should I marry him?", that is not a valid question.
However, if the question was something like "should I encourage my mother to reconsider the marriage?" and the answer was yes, I doubt there is any harm in doing that.
(I don't get the sense that he is asking you to marry him without your family's permission and you are trying to decide whether or not to do it. If that is your situation, feel free to submit another question.)
the purpose of istikharah is not to tell what will happen in the future but to indicate the best course of actions to be undertaken by the believer who put his trust in Allah.
One of the underlying notions in the Du'a Istikharah of Imam Zayn al-'Abidin, peace be upon him, is that the servant should be pleased with what Allah has decreed for him. In it there is a huge wisdom that the servant may realize later on, or even after his lifetime.
It is important however to consider istikharah as a du'a and a request to Allah, not a prediction of future events.
The Istikhara binds or guides the person who did it not others. It can be possible that the parents want guidance on the future of a proposed marriage through Istikhara, but that is for them.
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