Can someone who begins a voluntary fast break it?
It is preferable for someone who begins an act of worship not to break it.
Allah the Exalted has said {what means}: "and let not your [good] deeds come to nought!" [Muhammad/33].
However, if a person starts a voluntary fast (nafl) and needs to break it, they are going against what is preferable, but there is no sin upon them.
If a person enters a mosque and finds the congregation in the final tashahhud, which is more virtuous — joining them or waiting for a second congregation to catch the opening takbīr (takbīrat al-iḥrām)?
All praise is due to Allah, and peace and blessings be upon our master the Messenger of Allah ﷺ.
If a worshipper finds a congregation that is about to finish its prayer, and he hopes to catch the entire prayer from the beginning with another congregation, it is more virtuous for him to pray with this first congregation and then repeat the prayer with the second one — provided he does not intend to confine himself to a single prayer. If, however, he intends to perform only one prayer, then it is more virtuous for him to wait for the second congregation rather than joining the first, so that he may attain the reward of congregational prayer for every single rakʿah.
Al-Khaṭīb al-Sharbīnī, may Allah have mercy upon him, states: "If members of a congregation enter the mosque while the imam is in the final tashahhud, al-Qāḍī Ḥusayn held that it is recommended for them to join him in prayer, and that they should not delay in order to form a second congregation. Al-Mutawallī, however, affirmed the opposite view, and al-Qāḍī's own statement elsewhere supports this latter position, which is the relied-upon view. In fact, it is more virtuous for a person who has missed part of the prayer with one congregation, and who hopes to catch another congregation with whom he can attain the entire prayer within its proper time, to delay so that he may catch it in full with them. This applies when he intends to confine himself to a single prayer; otherwise, it is more virtuous for him to pray with the first group and then repeat the prayer with the others." [Mughnī al-Muḥtāj,Vol. 3/P.186] And Allah the Almighty knows best.
What is the ruling on a suitor (khāṭib) going out alone with his fiancée before the marriage contract is concluded?
It is unlawful for a suitor, prior to the marriage contract , to do anything that would be unlawful for any non-maḥram man — including touching his fiancée, being secluded with her (khalwah), or seeing her without her complete sharī‘ah-compliant covering — even after the recitation of al-Fātiḥah (This is a cultural custom to seek Allah's blessing (barakah) and mark mutual consent) and the family's approval [of the engagement]. This is because the engagement, without the formal marriage contract, does not render unlawful matters permissible. And Allah, the Exalted, knows best.
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.