Is it permissible for a woman to speak with non-mahram men for the purpose of seeking academic assistance, and what is the ruling on her joking with them, and does the same ruling apply to a man?

The default rule for communication between genders via social media networks is prohibition, because it is a source of temptation, and the Prophet, peace and blessings be upon him, said: "I have not left behind me any temptation more harmful to men than women."

This communication is permissible if it adheres to Islamic guidelines, such as: assurance against temptation, absence of lust, avoidance of women's images, necessity such as education, adherence to the extent of necessity, avoidance of submissiveness and softness in speech, and commitment to modesty in discourse. What was mentioned in the question about the conversation sometimes touching on personal matters and joking necessitates the prohibition of this communication. What is said to a girl is also said to a man, so it is not permissible for him to mix with women in any way that would be a cause for suspicion.