Is it permissible to repeat the Istikhara (seeking guidance) prayer, and is it a condition that one should sleep after offering it?
All perfect praise be to Allah,The Lord of The Worlds Istikhara is offered once, but it is permissible to repeat it, and sleeping after offering it is not a condition for its validity. And Allah Knows Best.
Is it permissible for the woman who is observing Iddah after her husband`s death to sit with her daughter`s suitor, although their marriage contract hasn`t been concluded yet?
All perfect praise be to Allah the Lord of The Worlds. May His blessings and peace be upon our Prophet Mohammad and upon all his family and companions.
A suitor who hasn`t concluded the marriage contract isn`t a Mahram*, so he must be treated as such. And Allah The Almighty Knows Best.
* The period a woman must observe after the death of her husband or after a divorce, during which she may not marry another man.
* In Islam, a mahram is a member of one's family with whom marriage would be considered haram, concealment purdah, or concealment of the body with hijab, is not obligatory; and with whom, if he is an adult male, she may be escorted during a journey, although an escort may not be obligatory.
Is it permissible for a Muslim woman to leave her house adorned and without wearing her proper Islamic attire?
A Muslim woman isn't permitted to leave her house adorned and without wearing proper Islamic attire. And Allah Knows Best.
What is the ruling on the chatting between a young man and his girlfriend?
Private chatting between the two sexes entails religious violations, and leads to prohibited attachment.