I think that chronological order is the smartest way to go about this, so let's start with boyfriend #1. The first.
The saxophone player: We had know each other since we were 11. We dated for 2-ish months when we were 15. He was my first kiss, and taught me that no matter what, always offer the boy the gum. And find a way to make him take it. It's important.
My other high school boyfriend was a co-worker. We worked at the pool together. We dated for 3 months until he tried to undress me in his car in my parent's driveway. Awkward.
The Ice Dancer: He taught me that hockey is an AWESOME sport, and that Ice Dancers are not all batting for the other team. Some are just coerced into the sport by Ice moms and crazy sisters.
In college, I dated lots of boys. Too many probably. The one that really takes the cake is the guy I dated the last few months of my senior year of college.
The Van Wilder: I met the VW through a friend when we were shopping at Wal-Mart for work, he was buying Count Chocula cereal. He taught me that it's okay to not have a plan for graduation, so long as your parents think you graduated from college 3 years ago. I also learned that pizza delivery guys should always shower right after work, and that some people make the choice to live out of their cars. I also learned that casually dating the same guy for 5 months is really hard -- eventually one person develops feelings (hint: it wasn't me).
After college, I thought I found the one, and only 7 months after graduating. The best part? His mom and my mom were best friends, AND we'd known each other since I was 14.
The mama drama: If a 30 year old man is telling his mom about your relationship, it's probably not going to work. Also, this will ruin your moms' friendship. But, I did learn how to throw back Jager like a champ during this relationship (silver lining? Probably not). Way to go. Side note, most 30 year olds who are interested in a 22 year old may have a maturity issue. Not that I learned this lesson yet, because right after Mama drama came...
Cabin in the woods guy: The first time I went up to this guy's house, I was positive he was going to murder me. He lived in an isolated spot in the Mountains. It was super-gorgeous, but also a little creepy. He taught me that southern boys are excellent cooks, there are more than 2 political parties in this country, that bluegrass and jam-bands are incredible, and started my passion for hippie dresses. Fun times, cabin in the woods dude. Fun times. Too bad you were 31 and so not ready to be settling down with anyone, much less a 23 year old.
The cyclist: Up to that point, the cyclist was my longest term relationship, at a whopping 6 months. He was an elite level cyclist, finishing up his degree at CU. As a cyclist myself, I thought it was great, at first. We could ride together! Hmmmm, nope, elite level anythings don't have the time, energy, or desire to do a "fun" ride with their girlfriends, who can't even keep up with an "easy" pace. However, I learned about the magic of the ManBerry margarita. I also learned that when he asks you to go pick up his butt paste from the cycling shop, you a) will probably get the wrong kind b) feel more awkward than a 14 year old in the "family planning" aisle.
Only one guy stood between the cyclist and "the one" (well, 2, but that's getting way too technical). He was during my phase where I decided to sow any wild oats I had. Get all of the cray-cray out. And my oh my, did I ever.
The Beer Ponger: This guy never left college behind. He had a good job, but was $45,000 in debt, with a $650 a month lease on a sweet car. His rental house was like any good college party house... lots of roommates, alcohol galore, kegerator, and parties 3-4 nights a week. We went out on the nights we weren't partying. He taught me that karaoke is a great excuse to party, that "Arrested Development" and "The Office" are two of the greatest sitcoms of all time, and to always lock your bedroom door if you're throwing a rager... you never know when someone is going to pee in your closet.
I hope you enjoyed my own personal walk of shame down memory lane. I hope you found it entertaining and informative. If you will excuse me, I'm going to go count my lucky stars that I have a wonderful man who puts all those other guys to shame.