Would plastic surgery have helped me meet girls in the past?

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No, sorry. I prefer to be discreet on WP. But I know for a fact that many girls---in real life, not just online---said "He's so gross!" when I was in my early 20's. And I know "gross" referred to my looks, and not my hygiene, because I took good care of my hair, clothes, etc.

Either way, no one referred to me as "gross" in over 5 years. And I like it that way. But I can't help but wonder how my life would have been different, if I got plastic surgery at age 21, to eliminate my gross looks once and for all, rather than wait until aging did it for me.

I've found that taking care of yourself and a good personality and confidence (or fake confidence) can go a long way to compensate for looks. Also playing a guitar or riding a motorcycle does it for some girls, really. You might have had more luck with them because you would have had more confidence in yourself and you would have acted differently. I know when I started taking care of myself and thinking I looked so much better I acted differently and that went a long way toward getting me dates. Also looking better did too, but I didn't change any features, just hair and makeup and clothing. I was never very pretty except for maybe a few years in my early 20's but I'm no dog either. I'm average but not somebody most would pick first from the neck up, and only from the neck down if they like the tall thin type with small boobs and no butt which is what I'm stuck with. Although my body has aged a lot better than some of the curvy girls that's for sure. I can still wear a two piece and look damn good in it but it makes me feel weird being a GILF. I think a MILF is pushing it, and a GILF is just over the line lol.

So, your confidence might have done more than the surgery would, although becoming beautiful is always better, but usually not an option for most of us.

That song by Janice Ian "At 17" really applied to me, but at 14 because taht is when I did something about myself.

To answer the OP's question, yes it would have increased your chances as long as the surgeon did a decent job. You said you were a 3.7 on hotornot, so the surgery should have at least brought you up to a 5 correct? Here's the thing, height is the #1 trait women find attractive. So how tall are you? If you're 5'10" or taller you're all set. So with a good face, height, and a little confidence and it would be pretty easy to get girls.

I'm short for a male (5'5"), and my face is a 5 (of 10). My confidence is low with women because I am really short. So even if I were to get plastic surgery to improve my face, my height would still be the limiting factor. Most women are taller than me so it sucks for me.

No way. I am slightly taller than that. There are plenty of shorter guys who do have some success at dating, which means they have infinitely many times as much as I do.

I'm 5'9". My alpha male friend was 5'8". So I'm closer to 5'10". Our body types were quite similar; I know 'cause I went swimming with him at the gym. But he got girls to take off their clothes within hours of meeting him, and had four friends with benefits. I was still a virgin at age 22.

Looks like height is not everything. Some years ago, there was a product on the market, called HeightMax, which was supposed to increase height. It was later proved to be a fraud.

If you didn't do it, you didn't do it. Stop with this BS, it doesn't do you any good.
Don't make yourself feel bad by thinking what-if...

Let's talk about what actually happened.
Nice that you grew out of it and great choice, those dancing classes!
It makes a woman feel sexy when a man dances with her who knows what he's doing.

That's how my uncle met his wife btw. They are still very happy.