Dain update 2

3/12- I have started recieving texts from Dain again. The time is 3:40pm.

Dain said: "TIMMY!!!"
I said: "What?!? Lol".
Dain: "Wtf are u doing?"
I said: "working hard as always of course!"
Dain said: "Lmao right."
I said: "so...whats up?"
Dain said: "N2m just out lookin 4 job"
I said: "What happened to your city job?"
Dain said: "I fuckd it off"
I said "thats smart, so now what?"
Dain said: "IDK yet lol"
I said: "good time to start a construction job."
...
It's now 8:13 Dain said: "can you take a joke?"
I said: "yes"
Dain said:"k..roberto says hi"
Dain said:"I applied at Tico"
I said:"Thats smart"
Dain said:"wat?"
I said:"Thats smart, they pay min wage"
Dain said:"U work there"
I said:"yes parttime 2nd job, lol"
Dain said:"yaya"
I said:"Lol I guess its still a job"
Dain said:"Yup"
I said:"Karen's a pain in the ass sometimes"
Dain said:"What's new?"
...

So now I'm wondering WTF? Should I ask him why he didn't talk to me for a month, and why he is talking to me now? Should I tell him that if he gets hired at Tico that it will only be for the summer and then they are demo-ing the building and re-building, meaning we will be out of work for like 2 or 3 months? Am I letting him walk all over me like a rug? Do I seem desperate for attention or has he come to terms with himself? I'm so lost. Apparently, I did the right thing and let him make first contact. But I really need something more to go on. Should I just ask him what he wants from me, i.e. friendship or more? Or should I just let it alone and see what happens? I really don't want him to play with me emotions, I have a hard enough time without that. And I'm still not sure about the joke question. Does he mean that applying at Tico was a joke or is there deeper meaning behind it, something about the last month? I feel like this boy is toying with me and I can't figure out the rules of the game.