TJ gave you a job, and a very important one.

Everybody knew how much Ian is important to TJ, the boss tries to keep him safe under any circumstances, even when he disappeared for a while, and obviously because of that, all his enemies tried to harm Ian too. Because Taejoon was almost impossible to reach, Ian no.

Ian chose a new life, but he can't run from his past forever and the time to face it has come, after Jason's death the whole mafia grounds in New York knew something will be changing soon. That's why you were supposed to watch every little step Ian does, to give any detail or off stuff, and you guessed Ian already knew about you considering that neither you or TJ wanted to hide the fact that Ian's being protected and watched, he'll be safe as long as the boss is alive. And you took this job seriously.

It was late and definitely cold, Ian was so crazy for leaving his apartment just go wonder around, and you had been dragged after him because that's your job.