<human>: So we met last year when I worked in retail. I worked there for a few months before he got back from being in another city for awhile. Then i worked under him for like seven months. When I worked there he was my assistant manager and we would only talk at work eventually we started talking about his lack of skill when it came to dating and I was assigned to help him navigate the dating world and became really good friends from it. 

We would joke that I was his Jiminy cricket because he would ask me for dating/girl advice since he was getting a divorce at the time. He had his relationships and I had mine. 

My friends thought it was weird that my assistant boss would text me at 3am about random encounters, but we were friends and i thought it was amusing. 

After I left to pursue my dream job, he became the store manager and we kept in touch. I haven't worked there in over a year now, and recently our conversations are different and we hang out more often. 

We're "talking" but nothing is official yet. I realized i liked him recently and, being a straightforward person, I told him I liked him. Since then we've been on a few dates, but it's just weird because I'm the aggressor in this situation. I need help in how this should be progressing and tips and such.

Condense the text into a few key points
<bot>: I'm "talking" to an ex assistant manager of mine and I don't know how to be the person pursuing someone else... Tips?