How to Ask Out My Childhood Friend?

i’ve struggled with social anxiety my whole life. anytime it comes to discussing anything personal for myself or whoever i’m talking to, it’s as if my voice box goes on mute and i can barely force any words out. anyways, i’ve had a crush on my childhood friend forever. he acts like a tough guy, but he’s always the first one to be there whenever someone is upset or hurt. he’s very goofy and and playful like a kid, but i’m like that too so we always bug the younger kids together to get off their phones. he has such a big heart. he dated this one girl for a year and a half. she was mentally and physically abusive towards him and he finally broke up with her a couple months ago. so i want to try and see if he wants to do something together now. i can tell he likes me too. he’s laid his head on my lap while playing on his phone, he’ll grab my hand and compliment my nail polish and my rings and then hold it for awhile, he’ll constantly poke me and come up behind me and swing his arm around my shoulder. and i catch him staring at me all the time and he’ll look away with a soft smile. i want to ask him if he’d wanna go bowling or mini golfing or something. but we’ve NEVER hung out one on one before over the many years we’ve known each other and it makes me have a lot of anxiety. usually when we’re together it’s me, him, his sis (who i usually am hanging out with) and my cousins (who usually hang out around him). so i’ve never been really alone with him. and we rarely ever text but i’ve been texting him every few days sometimes to just start a conversation and slowly get more comfortable. i’m afraid i’ll mess something up. but ik if i don’t do anything then i’ll never get the answer i want. he’s a really good guy. sometimes he’ll go quiet and not answer for awhile cause he usually keeps to himself and his parents get really mad over little things he or his sis does wrong. i just don’t really know how to go about this. i’ve never liked someone so much so i’m constantly overthinking everything i could possibly do wrong. i’m so afraid of messing up.