The Wednesday Wellness threads are meant to encourage users to ask for and provide advice and motivation to improve their lives. It isn't intended as a 'containment thread' and any content which could go here could instead be posted in its own thread. You could post:
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Notes -
My first thought is, define "sorta friends". At least in my book, "friends" is people I already talk to and get together with regularly and would be perfectly normal to ask to get together with. This feels more like this is a person who you see once in a while at work or school or something but don't talk/message with 1 on 1 regularly and have never done anything together. That's more of a loose acquaintance in my book.
A bit of a long-winded way to say that it seems like you're trying to jump too big of a gap with this message. Going from basically no direct communications to an overly fawning and formal date request is 90% chance going to seriously weird her out. If you don't already have extremely flirtatious contact in some other medium, you need to start much more casually. Something along the lines of, hey [name], want to come get [a drink / lunch / dinner / a movie / whatever is your kind of thing], or invite her to some group event that you're going to. Or send a short joke or meme or something to get a conversation started, and if there's actually a fun and active interaction, do the previous. If you actually get together, things just kind of go or don't go based on how your interaction feels, the formality of calling it a date seems out of place, and like it's trying to force her into a some kind of framework where she'll be pushed or obligated to do something she doesn't want to do.
The turn-off of fawningness is pretty hard for guys to really get. Guys don't tend to understand that until they've become successful enough at some job or hobby or something to have people fawning over them. It feels pretty weird, and it doesn't make you respect the person doing it. At best, you see them as an assistant or apprentice or something of that level. It almost tempts you to take advantage of them and abuse them a little, even if you weren't inclined to do that sort of thing. All of this is basically the complete opposite of what women are actually attracted to.
On the explicit "not a big deal", see the Frank definitely doesn't diddle kids video. That's a way over-exaggerated version, but the basic idea holds - the more time and words you spend talking about how you aren't or don't want to do something that your context implies you're going to do, the more people will disbelieve you. I understand that you're saying that because you're earnest and over-thinking things and actually mean it, but that's not how most readers, especially women, will interpret it. You communicate that it's not a big deal by writing the first part like it actually isn't a big deal, not by explicitly saying it isn't a big deal. Both of your paragraphs actually communicate that it's a super big deal to you.
I've always tended to over-think things myself as well. I've found it a good rule of thumb to chop out 3/4 of everything I write. It's probably worth a try for you sometime - write a message how you normally would, then spend some more time chopping out 3/4 of it by taking out everything that you may reasonably assume your reader already knows or understands.
But all of that said, this is all pretty normal issues to have for young guys learning how to interact with women. You're not a bad person or anything, there's just a lot of stuff to learn that seems odd and counter-intuitive at first, and is probably the complete opposite of everything you've ever been told by whatever authority figures you've trusted. You probably didn't have much of a relationship with her in the first place, and it's a tall order to build that over text when you haven't already done so in person, so you haven't really lost much. Just forget about this message entirely and don't try too hard to talk to her if you happen to run into her again anytime soon.
I like how you broke this down because I don't think I've ever heard anybody explain it so straightforwardly. It makes sense.
At the same time, I am left facepalming at the eternal incongruence between male preference for directness and female preference for a million layers of build-up and plausible deniability. If it works out and a longer term relationship forms, the not-initially-called-a-date meeting will probably end up being retroactively referred to as a date.
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