The Dating Nerd is a shadowy figure whose whereabouts and identifying details remain unknown. What we do know is that he is really, really good at dating. Do you think that can lead to a good relationship? That is not my opinion. There are lots of cool people out there. And sometimes a friendship can provide a great basis for a really deep attachment. And I can do is tell you why that is, so you have a better chance of figuring out whether your situation might become one of those lovely outliers where you end up happily in twoo wuv.
A typical scenario goes like this: Go on Facebook and look up someone who expressed unreturned interest in you, say, four years ago. Are you more interested in her now? Maybe marginally — maybe she has a better fashion sense now; maybe a more impressive career. But your basic attitude probably hasn't radically transformed, right?
Of course, there are rare exceptions here. Occasionally, people can go up a few rungs on the attractiveness ladder. Maybe you do a Chris Pratt and radically change your physique. Or you do a Mark Zuckerberg and go from being a random nerd to a powerful rich person. Personality, which is such a huge factor in attraction, tends not to change drastically.
Shy people stay shy. Outgoing people stay outgoing. Tortured artists, power-hungry maniacs, sports bros — they tend not to become drastically different people. Very happy for you. But you still might be facing an uphill battle here.
Well, asking your friend out in an appropriate fashion is really really hard. What this means is that the best you can do is have a hideously awkward conversation. At which point, she either expresses joyful surprise, or cautious curiosity, or apologetic repulsion. And either your friendship gets taken to another level, or it gets killed off, or it somehow survives the awkwardness. This is what you have to keep in mind — that you might well be rejected.
That it is, in fact, pretty probable that your poetic advances will be totally unappreciated. If you still decide to go for it, in spite of all my cautionary ranting, I truly wish you luck. Think you could use some dating help, too?