Looking for advice or complaining?

I swear yesterday walking up to my coworker crush a coworker from his diversion center said "here comes your flirty friend". Did he tell him I've been acting friendly? Or maybe the coworker who said it has noticed, he cracks dirty jokes at me a lot. One day I did hint to him that I might be interested in someone in the diversion center...
So if my crush told someone, was he complaining or asking for advice, I wonder...

After about two years being incarcerated on Wednesday he becomes free again. I know he doesn't have anybody close to him in the area, he has nobody to pick him up from the bus station when he's released. I've offered to help give him a ride at least to buy a phone so he can order uber. Is there some way I can invite a recently released felon to hang out without seeming weird? Like hey man I know you can't smoke you wanna grab some drinks? He might get moved to the opposite shift, I don't want that to be the last I see of him.