Lucy is like the mom of my best friend when I was a little kid. She's nice, but when you start getting to be too much she'll just straight call you a dingbat or something.
Five stars out of five, I love it. Except I rarely use "dingbat", maybe I will when I've got a little kid with little kid friends.
You, you confuse me. I think I've seen pictures of you in your radio situation, and you talk about that all the time, so I definitely imagine you in your radio situation. Except "bigfoot"? WTH, that does not follow. What must follow is that you're a pretty regular-looking guy appearance-wise, but you've got this nighttime radio show that you use the power of teh intartubez to broadcast globally, about cryptozoology and maybe your own little UFO fetish. It's a dear, dear fetish, not since you were fourteen years old have you ever been aroused without some sort of extraterrestrial "enhancement". Perhaps that's why you dipped your toes in the mafia room, to see if maybe the baked beans rumor could translate somehow... I've probably said too much, haven't I? You wear striped shirts either all the time or almost never. You wear hats when it's cold out, or raining, but you always take them off when you go inside. I'm pretty sure about the UFO fetish though.
im only 21 and i would never let someone else mow my lawn for pete's sake
You would if you had an Italian wife!
LucyDuke: The first thing that comes to mind is heavy Southern heritage that she tries to hide, accent and sweet tea tooth and all that. She flirted with a less exaggerated Socratic dialogue method as a young woman, but now she just out and out says when she thinks someone is an idiot. Probably prone to world play and innuendo. Shoulder length very light brown hair, green eyes, somewhat skinny build. Probably has some sort of martial arts training, probably not formal though, just in case. She probably abuses that training in a playful manner.
Underlined is spot-on. The rest... not even a little bit.

Born and raised in Rhode Island, baby, and I carry a knife "just in case".
I'm not sure about you.
I'm going to guess that you're a nineteen-year-old guy on his way to being an unjustly successful Wall Street type, for ten or twenty years, before you realize the futility of it and return to academia for something less degrading. You're generally pretty straight-laced, except you like to keep your hair long and usually don't cut it until your mother's nagging gets unbearable. You only wear hats when it's really, really, really cold out, and even then you hate to do it. Your assignments are never late, and one of your greatest frustrations in life is missing your transit connection (bus, subway, plane). You loved building model airplanes when you were a kid, and flying kites, but only when you were done with your homework. Your mother makes unbelievably good apple pie.
lucy_duke:
the kind of girl/woman who feels more comfortable in a group of men than with other females. being fairly attractive she definitely likes the fact that she's constantly being given the feeling of being desired within such a group, as well as the control from the background she has over this constellation.
maybe parents divorced.
knows what she wants from life and has a plan how to get it.

Some good stuff, there. Not all on the spot, but enough.
And I have no underscore thank you very much.
You're a thirty-seven year old unmarried skinny man with hair almost magnetically concentrated on the very
top of your head. Blame your avatar, I suppose. You have no body hair after an accident during a botched hazing for the fraternity you wanted to join - it was the fraternity of the guys with unusual yet unidentifiable ethnicities. You got in, but you left the school after your sophomore year to join the circus. After ten or so years traveling the country, you found a job as a middle school janitor, and proposed marriage to a local waffle waitress. She initially accepted and moved in with you for a few months, but tragically left you for a balloon-twisting-virtuoso clown named Frank when your very own circus came through town. Now you clean up after ungrateful "tweens", and you collect their secret notes in your dedicated shed to someday publish as a book, with your own "embellishments", to humiliate them.