Sister, it is your right to choose your own mate.
And it requires you to ask your questions.
You said: "how religious is he". That is the most important aspect that the husband and wife must be on the same page...other wise it would be chaotic, you should both be on the same page for your اخره as you are for your دنیا...
You have to choose your best mate for aiding in worshiping Allah. ( The Prophet asked Imam Ali, how do you see Fatima, he said: نعم العون علی طاعه الله meaning * what a good mate for worshiping Allah*.
In fact it's an amazing question, but you are asking it in a wrong way.
I mean everyone would usually say I am religious won't they? unless they are super-modern. Being religious to you means something different to me... You may be a very zealous person while I may not be.
You have to ask them what do you do for this and that...ask specific question then you would be able to gauge it.
Also if you think he would hesitate when speaking then why do you think he wouldn't also hesitate for writing!?!
You should both be honest...its a matter than could affect for an eternity so I just recommend that you set some principles for the discussion and then move on... writing on paper is far less effective than speaking...things get lost in translation or interpretation...and once the person starts speaking you would get a better sense on weather he is that mate for worshiping Allah or not.
Also I would recommend that you do several sessions of talk...not just 1 or 2...at least 3 so you would be sure and give a little time in between them. I don't know how old you are but the more younger you are the more likely you could become sensitive...so give it time and ask the advice of your peers...**but ultimately take it to your elders ( your father, mother,etc. **
As for the Hijab thingi... The idea is that you are allowed to have a softer Hijab...just so that the groom would see his bride better... but just for a short quick look not for an entire Fiance period... I mean it would be cheating if the person enjoys himself looking at a girl for 3-4 months and then saying hey I don't want you...I don't like you! Its just for the session so that the groom would know for sure that if he likes the girl or not... I mean imagine that if he didn't look at all until the moment that they are Mahram and then suddenly he would say: "OMG I don't like her at all" ( even if the girl is beautiful but that its just that he doesn't like her as a matter of personal taste)