Feel him out a bit first (tee-hee). Work out how much or little he wants you to help, and go from there. I'd appreciate you asking me if I wanted you to read the menu, but if he's legally blind, chances are he has some vision. He may even have enough to read print, either the "normal way" or through a magnifier of some kind. If you ask and he says no, accept it and don't ask again. If you ask and he seems annoyed, back off even further with similar questions. That's what I mean by feeling him out.

Same for vision questions. I'm happy to talk about my vision, but some people aren't. Also, on a date, I wouldn't want that to be the only topic of conversation, no matter how comfortable I am talking about it. Maybe ask him what he can see, since legally blind is a broad term. Based on his answer and whether he seems okay with the topic, maybe follow up a bit, or drop it after that one exchange. It'll depend on him.

Basically, you're going on a date with a guy. Treat his vision like any other subject which you find interesting and he may or may not--probe a bit, and base how much to go into it on how he reacts. Just don't let it be the only thing you talk about. Same for how much to help--he likely has strategies for most things, and how much help he needs will depend on his level of vision. He may have enough sight to follow you, or he may ask if he can take your elbow so you can guide him to wherever you two are walking. He may be able to read the menu, he may need help and not feel comfortable asking, or he may need help and will have no problem asking you to give him a hand. Just feel it out and go with what he seems comfortable with. Don't be afraid to ask at first, but gague his reaction and adjust your level of helpfulness accordingly.

I know this is vague, but it really depends on the individual. To summarize, treat this like any other social interaction, and read your date as best you can while you ask casually what he can see or if he needs help. Don't make a big deal of it, and don't be afraid to show interest if he seems open to discussing his visual impairment. For plenty of us blind people, blindness is just a thing in our lives, just as a job or where we live are things in our lives. We're open to talking about them, but it's not a big deal. We're also generally happy to educate people who are honestly curious, but that's not really the aim of a date. Also, I'm bad at brief summaries, it seems.

Have fun, and don't stress about this. Keep the vision and help questions casual, and adjust based on how he reacts to them. Ask questions if he's okay with it, but don't make that the focus of the date. If he uses a guide dog, don't interact with it at all unless he says you can. You'll be fine. Best of luck.

I feel like when I went out with ppl, vision hardly came up, especially at the beginning... what's tricky, is I'm just at the cusp of legally blind and pretty independent aside from driving...it's so dependent on how much vision someone has and what resources/ training someone has received. Some legally blind ppl can even drive. That's just all stuff you find out over time...I will say one thing that's tricky is societal expectations, especially of men, which is unfortunate, but can create challenges with accepting help, being vulnerable, and admitting insecurities. I feel like I also struggled to some extent with that stuff when I was that age. I would like, try to hide my vision issues more and not ask for the help I needed out of pride or whatever. This hopefully gets better over time, too :-)

Ask him how his vision is. There are 3 types of legal blindness. Visual acuity, peripheral vision, and central vision. Maybe a mix of three. Every blind person is different. It's not rude, just don't talk about vision all day or ask repeatedly. He'll tell you what he wants you to know when.
Don't keep asking if he needs help. He'll ask for it if he does. It sounds like you need to work on boundaries, most people do. Look for books by melody Beattie, and where to draw the line by Anne Katherine. That one specifically has a section on disability.

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So it's a blind date. Remember, it's not over there or over here. It's straight in front of you or to the left or right. There are steps going up or down. He can hold your elbow or he can hold your arm or you his but I guess you have to see how it goes. You can ask what he can see and if some type of lighting condition is better or worse for him so you know for next time. If he asks what is on the plate or where it is, closest to him is six o'clock, the top of the plate is twelve, you get it. If the waiter brings something let him know where they put it so he does not knock it over, sometimes they are quiet. He probably can't read your body language so there's that. Have s nice time.

Where did you meet?