Istikhara can not be repeated if it comes against what we mant. The only situation in which another Istikhara can be repeated is when the total situation changes and it becomes another matter.
Istikhara is not obligatory in every marriage. It is helpful if you are unable to decide whether the proposal is good or not.
The Istikhara which you did is for your intention, while the Istikhara which the boy did was for his intention. You need to wait till any change in the circumstances takes place, then if you remain unable to decide and you still need an Istikhara, then both should go for one joint Istikhara.
Thank you for your question. It is not obligatory to do an istikhara for marriage and if it comes out negative there is no obligation to act in accordance with it. A person should not take an istikhara unless they are unsure and do not have a preference for a certain outcome.
However, the spirit of istikhara is to seek the best from Allah, so if all of its conditions have been fulfilled the answer a person has been seeking is within the istikhara.
Istekhara in one matter is just once and there is no point in repeating the Istekhara on the same matter, unless the situation of the matter has changed.
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