Learn English – the noun form of “disturb”

to ponder

means to, over a period of time, think about the consequences of two or more choices in a decision. If there is only one thing you are pondering, you are pondering whether or not to do that thing.

to mull over

is the same as ponder - but you can mull over collective nouns, meaning you are trying to decide which one of the group. "I mulled over the candy, and found a good piece."

to contemplate

means to think about the consequences of something carefully, thoroughly, and for a long time. Typically when you contemplate something, you are deciding whether or not to do it, not picking among an array of choices. It has a serious connotation, likely due to the common phrase contemplate suicide.

to cogitate

I don't hear this word a lot. According to Google, it can be used intransitively, so you don't have to be cogitating about anything in particular. The other words here generally require a "target" to make sense.

to deliberate [on]

means the same as contemplate. When I hear this word, I think of court proceedings or meetings ("the jury will deliberate... etc.").

to ruminate

I don't hear this in speech very much. In my opinion it's a "less serious" version of contemplate.

to dwell on

means to think about something over and over. It could be the consequences of a decision not yet made, a decision that just has been made, or it could be going over past events in your mind. Dwell on can have a negative connotation, possibly that what you are dwelling on is bothering you or haunting you.

So, I would answer like this:

("depth 10k worths" doesn't make sense to me, so the second is a guess)

I have been dwelling on my son (all day) since he left home for college.

I have been mulling over my depth 10k worths because I will have to pay it by next week but I don't have enough money. So I have to find a way.

I have been dwelling on my new school project. I don't know where to start.

The government deliberated how to stop protest on raising student fees.

Well, usually when a man loves a woman and follows her around he actually tails after her.

I'm not sure if they are common but here are some of the phrases I heard:

1. to tail after - to follow someone or something
2. to follow someone around/about - to follow someone wherever they go (I would stick to this expression in your context)
3. to hound someone = to follow someone in a determined way in order to get something from them

Here's is what I suggest:

1. She asked him, "Why don't you ask me out? You're following me around like a puppy all the time."
2. She asked him, "Why don't you ask me out? You're tailing after me like a duckling all the time."