Weddingbee Blog

…he was really scared.

Just kidding. He was only mostly scared—not all the way scared. There’s a distinct difference between mostly and all-the-way, right college freshmen?

I met Bossyboots a very, verrrrrry long time ago, back when we were chumps at a local (yet national!) theater here in Chicago. I was the fresh out of college Stage Management intern; he was the seasoned lighting tech. He showed me around the theater, swooped me off my feet, and we lived happily ever after.

OK that’s a lie, too.

Bossyboots tells me that he spent our summer together with a raging crush on me. However, he neglected to clue me in to this fact. Consequently, there was a distinct lack of smooching. He says he even took me out on a date… a fact he neglected to explain. We went to a free show (as friends, I thought!), hung out on the free pier, and went to our respective homes sans romantic interlude. I don’t think I am the only woman out there that assumes that if the guy offers to pay for you, that means it’s a date—if he doesn’t = not a date. Of course, the reality that our evening consisted of completely free activities requiring zero dollars has no bearing on this assumption. Nor the fact that I am generally clueless about these sorts of things. I was raised in a conservative home—I didn’t go on a date ’til I was 18. Boys scared me; what can I say?

Anyway, the end of summer 2001 arrived. Bossyboots and I both moved on to greener career pastures.

Then, in 2008, I was walking the halls of my current employer to grab coffee from the dadgum [it’s broken again] coffeemaker, and who should I spy? A tall, blonde drink of water, that’s who. Out of all the companies in Chicago, Bossyboots decided to move on into mine!

We were both dating other people [while I was writing for a little site called (cough) Weddingbee], so nothing inappropriate was going to happen. Polite hellos were exchanged, but that’s about it. However, the moment my Facebook status went “single” after I called off my wedding… that man was hitting me up on Facebook every week. Nothing too forward, but he was definitely making his presence known. He says that his heart dropped when he saw that I was engaged, so he “wasn’t dropping the ball again,” now that we had a second chance.

I wasn’t ready to date right away, obviously, but when July hit, I let Bossyboots know it would be okay if he—you know—wanted to go out for a milkshake. Which he did. And we subsequently stayed out until 4:30AM.

Date #2 - Out until 4a

Date #3 - Out until 6:30a

Date #4 - Out until midnight (a girl’s gotta get SOME sleep - I’m not 22 anymore)

For the record, these were all PG-rated dates. P to the G, Mother!

At that point, we were both smitten, and the rest is the beginning of a great story. I still find him ultra-smoochable, and we still stay out until the wee hours, on occasion. Lack of sleep keeps you young…I read that in a book somewhere.