Is washing both openings (Istinjaa`) a must before every ablution?
Washing the front and back openings (Istinjaa`) is a must in case they have an impurity, but if they do not, there is no need for that, and Istinjaa` is not a condition for the validity of ablution.
What should a person, who doubts the validity of his Wudu, or over performs it, do?
One who doubts the validity of his/her Wudu while performing it should redo it until he/she is certain of having attained purity. But, if doubt was after having performed Wudu, then he/she should not pay attention to that as doubt after the end of an act of worship does not count. This is of course in case doubt was within the reasonable limits since once it goes beyond that, it becomes a whispering of the Shaytaan (devil) which he/she should ignore as the Wudu is valid.
Is it permissible to fast on behalf of the dead who died owing missed fast to make up?
His relative should fast on his behalf, and it is permissible for the guardians to give permission to non-relatives of the dead to fast on his behalf as well. And Allah Knows Best.
Talking to one's fiancée in Ramadan with romantic talk may lead to arousal, and if pre-ejaculate fluid (Madhy) is discharged as a result, it does not break the fast. However, it is advised to avoid actions that provoke desire and lead to this outcome. If semen (Mani) is discharged as a result, it does break the fast.
The discharge of Madhy doesn't invalidate one's fasting but it invalidates the ablution and his clothes must be washed because they are impure in this case. As for Mani, it breaks one's fast and making up invalidataed is obligatory, beside; a Muslim suitor should abstain from these matters during Ramadan and not to degrade the holy month to this extent. And Allah Knows Best.