Could you rephrase this so it makes sense? I’ve been pondering it for several minutes and getting nowhere.
15 years ago, I was the creep in a similar situation. I was a senior in high school and so was she, so no creepy age difference. We had a class together and I decided one day to summon the courage to ask her out, which I had never done before with any girl. Okay, so it took more than one day to summon the courage, but I finally managed (I was nervous because it mattered, but I was a geek anyhow, so I couldn’t pull off “confident”). I was so nervous that I came across like a fool. (I’ve been told before that some women find this “cute,” she didn’t). She said she was “trying to get involved” with another guy. So I backed off, kind of sad and disappointed that she didn’t want to bother get to know me. Months later, I hear her in class talking about how she was grounded because she went on a date with a 21 year old (she was 17). I assumed this was that guy, and that the relationship was over, so I decided to go for it again after another month or so. By this time, basketball season had started and I had tried out for the team (I sucked), and I later became the team cameraman. She was the team manager. I think she took that as me stalking her. That, and any time I did interact with or around her, I was nervous. I was a nerd, so cut me some slack. Right after the final game of the season, I approached her again (nervously) and said, “I wanted to talk about something we talked about a long time ago…” She cut me off and said “NO! I’ve told you before, NO! I’m not trying to hurt you, but I’m not interested…” And on and on. It hurt like hell, and I’d be lying if I said I didn’t tear up a little bit, ironically when she said “I’m not trying to hurt you.” After she finished her rant, I just said “Hmm. Okay,” and turned and walked away. My friend was standing nearby and saw the whole thing. I popped open the door and just said “I am really pissed off.” I saw that she was following us on the way to the parking lot. I was a breath away from turning around and saying “I just wanted to get to know you, no need to talk to me like I’m some kind of psycho stalker!” but I didn’t. And here’s why…I’m nice. I “suffer” from the same problem you with the face has. That is, I not only want to try not to hurt someone, I don’t want to inadvertantly hurt someone. By the way, I was really offended that someone implied that I was the creepy guy!
How interesting the OP is for me to read, because it gives me a chance to see a similar scenario from the other side. I had also caught a glimpse of this perspective in college when I finally did get a girlfriend who was quite attractive. Every now and then, I would see a creepy guy staring at her. Sometimes the guy was old, sometimes just weird, sometimes just uncanny for some reason. I spotted a guy at a restaurant staring at her one time and I stood in a spot to block his view. She spotted him and grabbed me and pulled herself close to completely block his view. It was disturbing, that look on his face (he was old, too) and she was genuinely spooked.
I always envied women, especially attractive ones, because they can have men worshipping the ground they walk on. Men rarely have this luxury, as women are more level-headed. However, I would not want to be looked at by creepy old dudes like that.
You could say, “I just can’t. You remind me too much of my father/uncle/father’s-fishing-buddy who passed away, and it’s just too hard. Sorry.” Tearing up would really help.
This way, he would finally see it as a favor to you to leave you alone. In his mind, he gets to be the hero, and you get to be left alone. Everybody wins.
YWTF, please, do not try to put yourself down for this situation. It is not your fault. This scummy guy is an asshole, and I am sorry that things have gotten this far. You need to be confident when you drop the hammer on him. You need to think of how much better your days at work will be when you don’t have to deal with him. Everyone has social challenges that they must face, and this is yours. No, it won’t be fun, it will be awkward, but it will be worth the effort in the long run.
Please, do not let this jerk bring you down anymore. You are a better person then he is, and you do not deserve to be treated that way. You have been very polite with your responses thus far, and he has not returned that courtesy.
I hope that you can muster up the courage to give this guy the blunt “No, I am not interested” soon. And when you do, be sure to update us all. We may all be complete strangers, but we will support you in any way we can. Forget about being a “wimp” and not having a “spine,” I know that deep down, you have enough courage to deal with this.
And then he would try to hug me. And then I would scream like Homer Simpson.
I understand better where you all are coming from.
Apologies ywtf, for sounding dickish.
I realise that YWTF is trying to be polite, but could this be the guy’s point of view?
He asks out an younger attractive female. She doesn’t say no, but gives a reason why not today.
So now every day he looks forward to asking his new friend out. Because she’s never said no, she just might be available today…
If I’m right, he’s got mildly addicted to this behaviour and therefore sadly it will continue until you explain things firmly to him.
Although rare (and much more likely in situations with alcohol) some guys will get hostile at even non-aggressive rejections. I love to go dancing and most of the time I want to dance by myself or with my female friends in a non-sexual manner. I don’t even dance with guys I like often due to the type of music I like the dance to. There are certain clubs where guys can get very hostile if you refuse to dance with them. Some of the time they will just come up and grind against you and then get annoyed when you remove yourself from their presence. I have a friend who looks like Cameron Diaz and she often gets guys following her from room to room. I try to be polite because hostile actions tend to increase the chance that there will be a hostile reaction. I’ve been called all sorts of names simply for expressing the desire to dance alone. Because of this, I always take a male buddy dancing unless I am at a gay club or another type of club where guys are more respectful of personal space.
You should go out to a dance club with me. I will sit at a table and drink beer, and won’t get hung up about who you dance with - I won’t even notice! You have a great night, I have a great night. Easy. 
I don’t do dancing.
You know, things DID occur in life for those of us older than our 20s and 30s. 
Back when dinosaurs roamed the earth, we women did have to put up with stuff like that. And no, we didn’t have much recourse. I’m lucky, I live in a state where there were always better, or other jobs to be had. Not every woman was that lucky.
A lot of stalkers kept just within the law, enough so that they couldn’t be charged with harassment. Many of them were quite well versed in what was and wasn’t legal, so they were able to avoid getting in trouble.