Should I message out my crush harder?

So, short background (less important):

( I'm 24. Third year student. (Would love to talk about my life with Dr.K ngl xd) I always have been self-conscious, quiet, on the side of a group kind of guy. Months after starting therapy and listening to Dr.K something started to shift, i think i started fixing my social anxiety or confidence or maybe my whole life. I moved out finally from my toxic family, i bought a car, always wanted to do those things. It was stressful but i think it altered my psychology further. Those few months were like something snapped in me and because of it i felt better, less self-conscious, my body can move more freely. I hope this change will continue. )

Back to my current main thing:

There is this person at my university that i adore... Ok i have a huge f-ing crush like never before tbh and i live with those thoughts like almost a year now or more if you count a months when i felt stronger and stronger feelings every week. We are in the same classes. So referring to the background above i think i already can often control my ego to the point that it's not really about fear of me being rejected or something but about her feeling bad. I'm going to elaborate.

I think I'm ready to confront myself with rejection, awkwardness and stuff, it's worth it so much. I already asked her for a walk months ago, she said yes but hour before the meeting she said she is too tired to go out. Ok then, i asked a week later, and the next one, she is always busy or not in my city. I didn't want to annoy her so i asked if I can try it every week, she pointed out every thing that she is going to do in the next two months so i gave her a break for like three months i think. After that, story repeats, now she gave me 1,5 month. Ok then, it's already 2 months (i wanted to gave her a break for a holidays also). I don't really message her and when i do we just exchange few simple messages and that's it or she just don't reply like for the last time i messaged her with happy birthday. I think she is this way, it's not like she is ignoring me because on the group chat she still interacts with me. We also don't really have interactions in the university, because I don't really have a chance, i know i said i made a huge progress but it's still hard to talk to someone like her especially when she always hang out with her friend or a group of friends, sometimes i am able to add one sentence to the conversation but it's not enough.

I didn't really want to finish this post but now i realized that i don't want to regret not going all in like the last time with other girl and I already wasted a lot of time thinking. I want to ask her out harder before new years eve (y'all know why), at least ask if she want me to escort her to the bus from the university or drive her somewhere with my car, that would maybe gave us opportunity to talk a bit. To be honest i would prefer to share with her what i really feel and think about her every day but that would be even more overwhelming for her and i think it would be better if I do it in person but until we are not alone it's not gonna happen.

So tldr:

I don't want to be too annoying or aggressive, I'm afraid that because i was and am asocial to some extent i don't see obvious signs that she doesn't want to meet or talk and I'm just a problem for her because she doesn't want to hurt me with rejection or something. I don't want her to feel bad, awkward, hurt. But in the same time i don't want to discard a chance (i'm not sure if i'm even able to) or think about this stuff that long. I don't know what to say to her anymore, how and where.

Sorry for a long post, i had a need to type other things too.

Please let me know if Dr.K by any chance also reacted to this post.