Bossybooty WIN
Sunday, January 2, 2011 at 6:50PM I realized that I don't think I've ever written about how Bossyboots and I became a "thing". It actually started way back in summer 2001 - that's 9.5 years ago, if you're counting.
I graduated from The Theatre School at Chicago's DePaul University in May 2001, with a BFA in Production Management. Immediately after graduation, I started work as a Second Assistant Stage Manager at Chicago Shakespeare Theater:
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I was fresh out of college, and I was excited to work full-time - life was a new adventure after four years of academia. I was assigned to a production of The Wizard of Oz, complete with creepy Munchkin puppets and all.
The way theatre works is that you rehearse for several weeks with the cast in a rehearsal space, then you move into the performance space a couple weeks before opening. In the theatre world - the show team becomes a tiny little faux family for those months that you're together. We eat together, dress together, go out together - nobody that works in theater is modest or shy (or at least not for long).
Anyway. When our show moved into the performance space, I met a very blonde guy named Bossyboots. He worked stage crew; I worked on the stage manager team - our whole crew were buds. Our team went out for beers, threw parties, hung out on Chicago's Navy Pier - all while running a show that performed eight times a week.
Unbeknownst to me, the entire time we were hanging out, Bossyboots thought I was cute and had "intentions." One night, we both had the night off, and he invited me to see another show that was playing at CST. Apparently, this was supposed to be a ROMANTIC DATE where Bossyboots told me what was up. However, these Bossybooty intentions were not relayed to me, so I thought we were buds hanging out, just like every other night of the week! We attended the show, and then went to our respective homes. Date FAIL!
After a couple months of Bossybooty FAIL, I threw a small party at my apartment after Friday performances. Everybody came over. Music was played. Drinks were had. This was supposed to be the BIG night where Bossyboots made "the move", but I had a few drinks too many, bailed on my own party, told Bossyboots and our other show-friend to spoon on the couch, and promptly passed out in my own room, as is proper for a young lady. Bossyboots says there was even a door slam (but that is NOT true!)
Bossybooty FAIL #2.
Just a week or so after Bossybooty FAIL #2, I scored a promising job offer at a different theater, soooooo I quit Chicago Shakespeare. No more Bossyboots; new theatre friends.
MANY years later, in 2008, I was walking the halls at my current employer, and what do I see? A new employee who was very tall, with very blonde head of hair. Who was this guy? He gave me a funny look, too. Clearly we knew each other - but from where? A few days later, I saw Blondie again, and this time he walked up to me... "Penny? Do you remember me from Chicago Shakes? I'm Bossyboots!"
Well, knock me over with a spoon.
In any case, he had a girlfriend; I had a boyfriend. No Bossybooty was going to happen, so we just said hello in the hallway now and then.
Fast forward to 2009 - he and his girlfriend had broken up; and Bossyboots and I were Facebook friends. He saw my relationship status change from "in a relationship" to "engaged" to "single".
Promptly one week after I went "single", that boy was hitting me up on Facebook... "So what are you doing?" "Want to get drinks?" "What's going on?" Clearly the shy Bossyboots of yesteryear was no more! Meanwhile I was busy recuperating from the single worst relationship of my life - an abusive, addicted ex-fiance. The online flirtfest with Bossyboots was one of the few fun things I had going on back then, in the midst of a broken heart.
Bossyboots' and my mutual employer sent our entire company on a great group vacation in summer 2009. Up until this vacation, Bossyboots and I had kept our contact strictly electronic and technically platonic. Once we were on vacation though, Bossyboots and I started hanging out, and as soon as we returned to Chicago, he asked me out on a real, live date. FULL DISCLOSURE: He HAD smooched me (PG-style smooching!) on the vacation after 24/7 hanging out, and it WAS the best kiss of my life, but.... you know how those things go - was it vacation fun or was there something real here?
We went on our first legit date on a Friday night. I hadn't been on a date with a new guy in 4.5 years, so there was champagne pre-gaming going on. (I was NERVOUS!) He picked me up at 7p... and we parted ways at 4:30a. After three successive dates that all ended after sunrise... it was pretty clear that we both had some crushing going on. (And I will SWEAR in a court of law that all smooching was PG! PG PG PG PG)*
A year and a half later... Bossyboots has been the best thing that has happened to me. He is kind and loving. He has a multitude of opinions and is a great match for my bulldozer personality. I respect and admire him so much, and he puts on a Bossyboots Comedy Show for me every day. He is so passionate about many things. He shows me every day how much he loves me, and he lets me do the same for him. He encourages me to be my best self and to go after my dreams. I am so thankful that The Universe gave us a second chance to find each other again.
He's also pretty dang cute.
And so, this past New Year's Eve, when Bossyboots asked me to marry him - I said yes. We be getting hitched!
I love this guy a whole lot. <3
Don't judge our bedraggled appearance! This photo was taken at 3a after a series of tears, champagne, and mucho family phone calls. We're cute in real life, I promise. ;)
*PG!
Bossyboots, Life, Love and Relationships
Reader Comments (73)
Yay! What a great story and I'm so glad you guys found each other again-- it's funny how life works, right? I'm so excited for what the future holds for you two :) Congratulations!!!
Yay!!! What a fabulous story and I'm so happy for you both!! Congratulations!
Oh my gosh, I have the biggest lump in my throat! It's amazing how things work out for the best in the end. You both are wonderful people, and both deserve every happiness. Congratulations!!!
That last paragraph has transformed me into a certified blubbering mess. It just goes to show that everything works together for good and that love never fails! I'm SO happy for you + Bossyboots... Congratulations!
Eeeee! Congrats! I was about to comment about how cool it is to see places I go to all the time (DePaul, CST) in a blog post, but your last paragraph was much more exciting. So happy for you!
Fate I tell you. It's an amazing story to tell your future kids (if you want some) I am so happy for the both of yous. Congratulations once again. eeeeeee!!!
Congrats! I am so, so, SO happy for the two of you!
Yay! Yay! Yay! Yay! Yay! Yay! Yay! Yay! Yay! Yay! Yay! Yay! Yay! Yay! Yay! Yay! Yay! Yay! Yay! Yay! Yay! Yay!
I'm so so so thrilled for you both! Congratulations!
Ahhhh! So excited for you guys!! :)
Congratulations!!! What a wonderful beginning (albiet long begining :) ) of a life full of love.
Woohoo! Yay for Penny and Bossyboots! Bout time a good girl and a good guy find each other again and live happily ever after. I've been rooting for you. :)
YAY!!!! Hooray for Penny and Bossyboots! I loved reading this :)
Congratulations again to you both!!! I am so happy for you and it's wonderful to read the whole story. We must see the ring! :)
So I'm reading the story, holding my breath and hoping. I love when I guess the ending correctly! CONGRATULATIONS!!! What exciting news for the new year!!
Congratulations! How exciting - great New Years for you both.
CONGRATS!!! I was planning my wedding and following you on Weddingbee when all that horrible-ness happened. I was devastated for you and was so happy when you started blogging about Bossyboots over here. You deserve the best! Soooo happy for you both!
So happy for you guys! That is a wonderful story. You deserve the best! Congrats!
Sigh. This made my week.
Ok, when I read the title of your post I seriously hoped it was going to end that way!! CONGRATULATIONS!! SO happy for you!