How long after you break up with an ex can you date/be friends?

We broke up a year ago. He dropped out of school and pushed away most of his school friends. I know where he works. He's had drug problems and struggled with anxiety and depression in the past. I want to go by his work and say one of the following:
Hey, I'm sorry about everything that happened and I just want to let you know I miss being around you and if you ever want to hang out, let me know.
Vote A
Hey, I'm glad you're okay, I know we aren't close anymore but if you ever need to talk to someone or be with someone I'm here.
Vote B
Hey, sorry about everything. I'm glad you're doing good, let me know if you need anything.
Vote C
Other
Vote D
Select age and gender to cast your vote:
GirlGuy
How long after you break up with an ex can you date/be friends?
6
2
Add Opinion