Directness (advice needed pls)

Today I am nervous. Why? Because I am hoping the boy previously mentioned will ask me out soon. Preferably tonight. :D

Some background:

1. Last week we went out several times. And then we spent the weekend together. I had a great time. He asked me to be his girlfriend (aka, be monogamous, which I'm totally cool with b/c I don't date multiple guys at a time anyway... I just don't think I could handle the stress, so this was pretty much a given for me anyway). We text everyday, off-and-on, usually several hours apart, during our respective breaks at work, etc, usually for some interesting conversation. I do not initiate all of these texts, I do initiate quite a few, but he always makes sure to end them. In other words, I'm pretty sure he still likes me.
2. Right now we don't have any plans to see each other in the future. I'm a planner, I like knowing what I'm doing in the near future at least. I also don't typically leave stuff open for people, assuming that if they want to do something they'll ask me with enough time to book them a spot.
3. I'm a very direct person, I don't take hints very well. I expect to be asked a direct questions so I can answer it.
4. He doesn't strike me as a very direct person. A couple times I've had to repeat back what he said to me and ask if he was asking me on a date.   >.<

So since Sunday, no mention has been made of a future date. Last Wednesday I went with him to Karaoke night at a local bar. This is a weekly thing for him. He's mentioned that he's excited about today (this Wednesday), Karaoke night. I was kinda hoping to get a repeat date out of the deal and go to Karaoke night this week, there has been no direct question though. Just him mentioning it several times.

I should probably just assume he doesn't want me to come unless he asks right? I shouldn't hint that I'd like to go?

And if I ask him to do something or hang out Friday night is that being too aggressive? Should I wait until he asks me to do something??

I know these are the kind of stupid questions that get girls into trouble (because in all reality, he probably doesn't care one way or another), but I can't help it. I worry that because I like him so much, and because I miss a steady, stable relationship so much, that I'm going to turn clingy and scare him off. 

I am not good at this dating thing!! Advice/Reassurance would be very welcome!