I’m going to admit that I was pretty disappointed with Don Draper’s actions in the season finale of Mad Men. To quote Christina Hendricks’ character Joan: “he thinks he’s the first person to marry his secretary.” Yeah, novel idea there, Draper. I try not to get emotionally attached to shows or characters, because as my mom has been telling me since I was a kid: “It’s just TV, Amanda, calm down,” but Mad Men has firmly secured itself in the forefront of my thought process. While all of us at The Gloss have our particular obsessions with shows, or in some cases, whole stations, (yes, I’m talking to you Lilit and Jennifer), I’m pretty much living a What Would Don Draper Do? lifestyle over here. In fact, I’m thinking about having bracelets made. Don Draper would apparently dump his educated, sophisticated, girlfriend who was there for him when shit fell apart for his 25-year-old secretary. Yeah, Megan is kind of hot, she can speak French, and I’d probably do her, but marry her? Come on.

So after I threw my remote control at the wall, yelled at the TV and stormed out of the room all mature-like, I started thinking. Literally, I looked up and voila! (see? I can speak French, too), there was a light bulb floating above my head and a realization was had: I would never marry my boss.

I have had three male bosses in my life. All were educated, successful men, who, I’m sure would be considered good-looking by someone’s standards. Actually, two of them are pretty easy on the eyes, the other one looks like a cross between a maniacal lizard and Howie Mandel. Having been an Office Manager (or rather a glorified secretary) and/or an Executive Assistant to these three men, an intimacy definitely developed. While the female bosses I had in my past were fairly self-sustaining and could function quite easily with little assistance, working for these men was like babysitting absent-minded children. Besides making sure they stuck to their schedules, I was also relied upon to get them coffee, order them lunch, pick out gifts for their kids’ birthdays, send flowers to their wives when they were in a fight, and make sure that girl he drunkenly gave his number to at that Yankees game is perpetually kept on hold. I walked away from these jobs with too much information: allergies, preferences in deli turkey, boxers vs. briefs, and for one, his drug dealer’s number on speed dial. And although I was happy to leave these jobs and bosses behind (I’m “friends” with one on Facebook), a part of me ached to lose them.

All of sudden I didn’t have someone that needed me, someone to take care of nine hours a day… my hands were empty. I was back to ordering coffee for just myself, but of course, not before stumbling and railing off a former boss’ complicated order first by accident – I guess we could classify that as withdrawals. That being said, I understand the bond that can form between a male boss and a female underling.  One boss in particular was so cruel, then so nice, that I couldn’t figure out if I was in love with him, or if given the chance, would have put a hit out on his life. It was confusing. I wanted him to succeed and fail all at once, I wanted him to stop making me crying every other day, then making up for it by buying me expensive lunches I couldn’t afford otherwise.

It took me awhile to realize the difference between comfort and love, the fine line between need and want, and how to shake that maternal feeling that develops when the majority of your day revolves around the needs of another. The lines can get fuzzy, the rules can get blurry, but the point is to stay on your side of the office and separate professional and personal – even if he hugs you too long sometimes after he’s made you cry again.

Some women will say it’s how attractive power can be that perpetuates that desire to date your boss, but power has never been a turn-on for me. I want to be an equal, and I’ve never cared for pedestals. While I’ll never give up my fantasy of having sex on my desk after hours with some hot coworker, if it does happen, it will be just that: a coworker, not my boss. There’s nothing less attractive than going to bed with someone you’ve been mothering all day, someone who treats you like you’re beneath them, and scolds you relentlessly just because you didn’t realize that it really was [insert fancy celebrity name here] on the phone and not your kid brother making a joke again. So yes, if given the chance, I wouldn’t marry my boss – even if he did look like Don Draper.