If you're gonna go for it with your crush- choose some non conventional first dates. If you go about it the same way that you did for others, and it didn't work out, you may enter this thing with one foot out the door and feel like its failed before its started.
but as a side note, boredom in relationships often comes from boredom in your own life, or if you enter a relationship looking for something specific. Sorry if that sounds super rude or If I'm way off base haha- but I just mean that having a good time with your friends, and being happy to spend time alone, will bode better for when you get into a relationship, because then you're not constantly looking to do something, or feel like you've always have to talk to fill silence or force chemistry.
Also- less serious- but you should have a lot of fun. i can't even count how many times my first date with someone has been 'get drinks at the pub'. establish what you want to do but also be receptive. Ive had some really good times doing non date-y things, and even though it didn't go anywhere, I feel like it helped me with the same problem you're having.