I shot my shot

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Her brother is alright with the dating but seriously, any brother would smash the head of a dude that crosses a boundary with his sister - friend or not.

What boundaries?
The brotherhood of guys?

I don't see the problem.

While I was getting dinner, he came up to me to get my attention and said hi, and apologized for everything, started asking about my weekend and everything. And then when I gave him a chance to exit the conversation he followed me to get dinner, and kept talking to me. So we talked about plans and everything. Like setting something up.

I still did not get the sense that he realized my intention, but maybe I am just dense. There was a lot more laughter from him, it actually bordered on seeming nervous at times, but he seemed very interested in talking to me. Like I said, he sought me out and all that. Big friendly vibes at the very least. Like... if he knew I was interested and was not interested himself, I feel like he would have not been so eager to speak to me for like half an hour while we were getting dinner.

I did not get flirtatious vibes, but to be fair, we were in the middle of a public campus sidewalk in the freezing cold, with face masks on. So, I don't know what flirtatious vibes would have looked like in that context.

I remain confused but slightly more uplifted?

Lucky you lucky me.

Tragic, I know.

Yes. I think it would be a good idea for you to do this.
This also may get him to explain if there are any restrictions imposed on such a relationship due to religious reasons.

I was thinking about what you said about your meeting with him. You said that the opportunity for you both to speak freely was there due to one of his friends being sat close by.

Thinking about my experiences with a religious girl, some religions (especially those who forbid sex before marriage)
will force young ones to always have a chaperone present during any times that you both are together in order to prevent you two getting too close and having sex.

Not all religious people do this, but it would be worth you clarifying as to whether this is why his buddy was hanging about the first time you met up.

As obviously, if you had plans to have sex with him before marrying, or perhaps even having sex with him and then not getting married, this may be a problem if he or his religious leaders forbids such activities.

As previously mentioned in my first reply, this is how it is sometimes when it comes to getting involved with religious folk, so can be difficult from the start.

If he is serious about his religion, it may require you to convert in order to be together.
And if you do convert, it still may require you to get married before you can have sex.

Sorry to be so blunt, but this is how religious people can be, which I myself didn't understand when I got involved with my ex-wife. If i had known what was involved to simply go out with my ex-wife, i wouldn't have bother.
As I didn't believe in her religion so I was always an outsider and didn't like the life of being told what to do by some religious nerd, who more often than not didn't keep his own religions rules as well as I did, even though i didn't even believe in his Religion.

So. Yup. I would get him to clarify re chaperoning if i were you.

I sincerely hope for your welfare that it isn't the case, but it does all sound a little too familiar to me.

If it does go the religious way, you will have a lot of thinking to do, as it is a massive decision in your life.
Do you convert which means learning to live as a Jewish person, or do you not, and find someone somewhere else.

From my understanding, people who are highly religious don't generally do "dating" unless they aren't practising members of the religion. So this is something you will have to find out, before you get too deeply involved, and you get hurt or heart broken...

Sorry to be the bearer of bad news. Religious relationships are often complex, and not always understood by us non religious people. Not a life that i want to live.
Good luck.