Is it permissible for a person who has to make up for missed fasts to fast six days of Shawwal (the month directly after Ramadan) before making up for the missed fasts?
Yes, it is permissible for him/her to do so, but it is better that they make up for missed fasts first. 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.
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 for a woman to wear underwear while performing Umrah?
Yes, it is permissible for a woman to wear underwear while performing Umrah. This is because she should keep her regular clothes that cover all her body while being in a state of Ihram (ritual consecration) for Hajj, or Umrah. However, she should uncover her face and hands, but it is permissible for her to let her head-covering garment drape from her head down over her face when non-Mahram (i.e., marriageable) men pass by her. And Allah Knows Best.