ok i started up doing JV football we have wieght liftin yadayada so i go there ppl waitin outside talkin and stuff (casual talk) they're bout 2 or 3 years older then me maybe 1. i wana know how to go in and get in their conversation then get to know them then be friends its bout 7 people there and conversations over the phone is hard too it gets boring after u say hello then i get into thinkin and stuff on wat to say. should i go try striking up a conversation with a shy person i dont know (it was bout 2 shy ppl there) and i was bout to strike one up ask him how old is he n wat school he go to then get started up in one but i want to know how to strike up conversations and getting in conversations with ppl u dont know and is kinda older than u and get comfortable doing it

....honestly man, walk up to them, say "hey, what are you guys talking about?" just talk about w/e they are saying....

Wouldnt walking up to strangers and butting into their conversation seem rude?

One thing to try is listening in on their convo. Not to spy or anything, but to see if they're talking about anything you can relate to. If they start talkin about, say, baseball, and you're a baseball guru, then get your butt over there! Just be like, "Hey, are you guys talking about so-and-so baseball player?" and just sneak right into their circle.

lol we they were talkin bout sum dude that deck'd this other dudes face in swollen his mouth, I was listenin but i couldnt come up n say nothing also those not the type of ppl u can say "hey wat u guys talkin bout" or would talk bout baseball its all good tho