You get what you pay for, and sometimes that means a gut, acid reflux, and a first-name basis with the elderly woman in charge of making sure people swipe their card that thinks you would get along great with her grandson. It's bad enough you got the proverbial wool pulled over your eyes and signed up for the excessive and, more importantly, expensive full meal plan, but having to go out and buy new sweaters that are big enough to be pulled over your stomach is the icing on the really dry cake you ate next to that homeless guy you gave one of your guest meals to before Sociology.
Losing your half-finished term paper, entire iTunes Library, and high score on Snood to a particularly hard to grasp Nalgene bottle of milk pilfered from the dining hall is bad. Losing that all because, despite ordering one six months ago, you still had not gotten around to backing up all of your files on an external hard drive is the absolute worst--at least as far as first-world problems go. If the whole meal plan thing wasn't such a ripoff, you'd probably think it was karma. Which, thanks to your clumsy hands, you'll have to finish reading about on your smart phone, or tablet, or roommate's laptop.
It's well documented that playing the guitar will do wonders for your social life. If you can strum the right notes, pluck the right strings, and brush the hair out of your eyes at just the right time, all of the girls will want you and all of the guys will want to be you. Learning how to play the guitar, however, will have a far less advantageous effect. All of the guys will want to beat you, and all of the girls will want you to move away from where they're catching rays out on the quad. Practice may make perfect, but it also makes roommates "forget" your pillowcase isn't a wastebasket.
The only statement you're making by wearing a newsboy cap around campus is that you have absolutely no idea what looks good on top of your head. That, and you noticed your hairline was receding EXTRA! EXTRA! fast. There isn't one person, who doesn't already own a newsboy cap themselves, that will take a gander at your new gear and say, "Now that is one dapper individual." And if they do, it's because they're either making fun of you or one trip to the vintage shop away from making the same mistake you did. Hats are for keeping heads warm and keeping a lid on the occasional bad hair day, not ruining social lives.