The time I took a [m]uch older coworker [f]rom 0 to 100 on another coworker’s couch [older man, younger woman] [coworkers]

This story happened several years ago, but each time the anniversary passes I fall prey to a new flood of daydreams. Since I’ve been so turned on by all of your contributions, I though it was time I share mine. Throwaway account for obvious reasons.

I was 22; a young, female, wide-eyed copywriter. I was new at it, but a really hard worker—and I began to rise in the ranks of our mid-size company about six months in. At first, I felt like I had to make up for my youth by being more buttoned-up, formal, and perhaps overly respectful to my senior colleagues…but time made me comfortable. As I grew as a writer there, I got closer to my coworkers, letting my guard down and letting my “outside of work” personality shine through.

Even so, I worked with a variety of people across my portfolio of clients, and some were more interesting than others. The last person I expected to have a personal bond with was Oscar, a creative director on the most boring of all accounts. (Seriously, I wrote copy for infomercials selling knockoffs of the NutriBullet blender.) We worked together on a couple of random projects, and although he had kind of a reputation in our company, I never even saw a glimpse.