Question
If a Jew were to eat at a non-kosher restaurant, is it preferable that he not wear a kippah while doing so in order to not mislead others? The reason I am asking is because I personally know a couple like that. They wear the costumes of Orthodox Jews (the husband wears a kippah and the wife wears an orthodox style hair covering and long skirts). But they dine out at non-kosher vegan restaurants. They are not intentionally being rebellious. This is just the level they are at. The first time I met them, I saw them entering a non-kosher vegan restaurant in a shopping center I frequent. Seeing what appeared to be an orthodox couple entering this restaurant, I asked them if the restaurant was kosher because I wasn’t familiar with it being on the list of kosher restaurants in town. They explained to me that it has no supervision, but they are comfortable eating at almost any vegan restaurant. This encounter led to a friendship with this couple in which I learned they also drive to synagogue on Shabbos when the weather is not conducive to walking. When non-orthodox Jews enter non-kosher restaurants, we think of this as normal behavior on their part. But the very sight of a man in a kippah entering a non-kosher restaurant might confuse others into believing it is kosher. So wouldn’t it be better if a Jew who plans to eat there remove his kippah before doing so?

Question
I grew up keeping strictly Cholov Yisroel. My parents did and still do keep CY, and in their minds, any non-CY dairy or any kelim that have been in contact with non-CY are just as good as treif. They never ate or allowed me to eat at the homes of anyone who is not strictly CY. The local orthodox rabbi our family follows stands by all of this. At the same time, 90% of the orthodox community where I live does not follow CY, including most of my friends. I’m talking about strictly Orthodox Jews. I feel really constricted and like I am missing out on so much by this CY restriction. I’ve had enough of it and can’t take it anymore. I am a fully grown independent adult now with my own job, home, and social life. I want to give it up and eat Chalav Stam, but I know my parents would be angry at me and our rabbi would also disapprove. How terrible would it really be if, despite all this, I stopped following my family custom? Would it be a violation of Torah law? Would you, as a rabbi, apply the word ‘sin’ to the act of abandoning CY when most Orthodox Jews already don’t follow it, and when widely respected kashrus organizations like the OU approve lots of non-CY foods.

Question
I am interested in becoming more religious as a Jew. I like almost everything about Orthodox Judaism. But there is one thing I can’t get myself to do. I know that orthodox women wear skirts all the time. Supposedly it is about modesty. But I can’t see myself wearing skirts daily or even occasionally. The irony is I feel immodest to the point of feeling naked whenever I wear a skirt or dress. I feel paranoid that men might be looking under my skirt, no matter how long it is. I just feel so unsafe. I don’t have these worries when I wear pants. I want to become orthodox and be accepted by the orthodox community. But I fear this might be a barrier. Can I still be orthodox even if I wear pants if I do everything else orthodox women do? Can I go to an orthodox synagogue? Can I take part in gatherings in the orthodox community?