everything depends on who he is and how he deals with stress. Maybe try to plan a small, low key, event that he and you will bond over, anything to get him away from the problem for a few hours. start small and ask if he'd like to walk you somewhere, some space is good but guys are not good with emotions, we feel them but we are terrible at communication and identification compared to you so he may not want to do anything but it's best to make sure he knows you want him to stay in your life and don't judge his failing or family issue.
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Well, with some guys it's just knowing that someone is there makes you feel better. I would say maybe next time you see him in person ask him how he is doing and ask him if there is anything you can do to help. If he says "there's nothing you can really do" then just say "ok I'll be here for you" or something akin to that
You already did as much as you could. You don't have to do anything more. If he is a decent person, he will appreciate that. You could try to contact him the next week or something
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Just send him simple encouraging notes. Things like, "you matter to me" "things will be ok in time" "keep on the sunny side" "smile, because you are awesome" or a gif of woody that says "you got a friend in me" this is about you showing him that you are there. Also, space can be good at times, but the harder down someone is the more you need to not let them retreat.
It's perfectly okay to text him again to let him know you're thinking of him and there for him. Just don't make the dreaded over texting mistake so many guys are guilty of with girls.
give him space. he will come to you when he needs you. looks like you like him.
just tell him your here for him and if he needs you he needs you if he doesn't he doesn't
Blow job would be cool
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