Should i feel this way... Or can i still walk around people i know with my head held high?

Not at all, I think you've had a bad run of luck with guys, but only cause your hanging out with these idiots! Alot of guys are immature around this age, also know who you wanna date, and make sure they are 'good' people, because clearly the guys you have selected sounds like down right loosers. Chin up. you'll look back at this and think what idiots they were and what they missed out on!