Would this be a stupid prank?

Elaborate, and the timing would be tricky. It would be very hard to pull off.

But I think it’s a great idea and could be a lot of fun. Go for it.

Ultra creepy.
“I will follow you at night and cut you into pieces in a dark back alley” kind of creepy.

I would find it creepy.

I guess I’m not sure of the significance of the ‘prank’ aspect. Why not just do it for free the normal way, with sittings, so she can look and feel her best?

To me, a better prank would be to do the sittings and create a ‘prank’ version as your presentation to her, in private, that is ugly or comical, or looks like you have no talent, then present the ‘real’ one afterward.

Also, worst-case scenario, if you are a man, you could actually be prosecuted as a stalker if you did it wrong, and at her place of business without her consent. I’d be upset and confront you about it personally, if you were a stranger to me.

Creepy. Just do it for free as a lovely gesture?

Too damned creepy.

If you do it from a photo, I guess she would look different than at work.
Maybe you could have that one ready, but sketch her while she works, only, make it to where she looks more tired and unkempt in each progression.
Then, the finished project would be a relief, and she could keep the sketch for the joke of it.

Ok my instinct was right, it’s definitely creepy. Although to be fair there are many pranks on YouTube that are weirder than this, but people still find funny.

By the way, the prank is actually meant to come across like I’m a stalker. But then my friend comes out and says that it’s a joke and that I’m giving her the portrait for free.

@rockfan It’s not funny to feel you have a stalker, even for an hour. Just. Not. Funny.

Ok I’m glad I asked this question first.

I wouldn’t consider this a prank. The creep factor can be reduced. The filming of the event would be the part that troubles me most. IF you were able to clandestinely pull it off, you should give the girl full control over what happens to the recording, retaining copies only with her permission. I think you might actually be able to get away with it if you can actually confine the event to an hour.

What @janbb said. Confining the time, control of film, all of that not worth the hour of extreme distress to her. What if she sick management on you or calls the cops?
Sorry, @stanleybmanly, even with all the strictures in place, unless @rockfan fully discloses at the beginning of watching and sketching, the creep factor is not reduced.
A young woman waiting tables at Chili’s is the target of so much inappropriate attention that more, even as a “prank”, is just mean.

The words unnecessarily creepy comes to mind. It has NO resemblance of a prank to me!!!

Your friend who works there with her could tell her that she knows someone who would do her portrait. That way she has a choice, without all the other questionable aspects you were planning.

Try to do it when she’s not at work! She might be real busy and her boss might get pissed!
A good prank is one that does no harm in any way!!

There are so many things that can go wrong here so I would suggest not to execute it.

I don’t think I explained it very well. I’m simply going to be drawing at the table, minding my own business. It’s not like I’m setting up an easel, grabbing attention to myself.

If she’s your server, she’ll see it. If you haven’t asked her if it’s OK to draw her, it’s creepy. That simple.

Drawing might be fine if she doesn’t notice but recording would too much creepy..!! I don’t think anyone can ignore it.