Hasn't happened to me yet because I keep it all fairly low-key in this Digital Age. Although, I had a tonne of assignments to do in the last five weeks or so and opted to use the typewriter for a couple of them because I was just getting sick of staring at computer screens and found my vision blurring a little, as well as having to use eye drops a little more often throughout the day.
I don't know what my lecturers will make of it, since I haven't gotten any of these assignments back yet. I'd like to think that, since most of them are in their mid-50s or older, they may experience a slight nostalgia at seeing these documents typewritten.

I used my circa '46 Royal Quiet De Luxe for one assignment and my '66 Olympia SM9 for the other.

Actually, I have had fellow students say that to me in the past. Wow, that font looks like typewriter! They didn't believe me then that it was at typewriter...at least I dont' think. 

I went to Harbor Freight looking for some cleaning supplies for the old typewriter I'm working on.  I had a list that I had scribbled on a typing test scrap.  The guy who was helping me looked at my list and said, "wow, is that the actual typing?  It really works!" 

When I took two typewriters up to my son's class for a museum day (what got me started on this) the kids were amazed that it, "prints out right as you write it!!!"

Being a student in high school with a bunch of people who have never seen a typewriter before, I still get some remarks to this day even though I've been using it since October. Some kids ask to see my typed documents, and either say "Oh that's so cool!" or "Why don't you use a computer?" or something like that. My teachers either say nothing, or are mildly pleased with it. Especially the ones who have been there for awhile. But all think there's something wrong with me. But I don't care. When ever I hand in a typed document, I feel a certain sense of pride, like I'm helping continue an ancient art that has disappeared in my town for centuries. So I guess I always get a surprised reaction from people. But like I said, I feel pride in that reaction.

I mainly use mine to send notes to people -- thank you notes, or notes accompanying a newspaper article or the like.  They get a kick out of an old-school typewritten piece of correspondence.  I realize the rules of etiquette dictate a handwritten note if it's a note of thanks, but actually something typewritten strikes me as even more meaningful: Generally I say more in a typewritten note than in a handwritten one, since the text is smaller!