Why I Would Never Marry My Boss

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.

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    • Patty

      Thanks for the spoiler there on Mad Men!

    • Foush

      Honestly, love the post, but could have done with a SPOILER ALERT. ARGH. I just almost threw my laptop across the room.

    • erin

      yeah! i’m only halfway through season 1. :)

    • Mel

      Did anyone else notice that Megan is holding a doll in this photo?

      • Lilit Marcus

        Yes! I think maybe they got this shot from a rehearsal or something, and they were using a doll as a stand-in for the baby. After all, there are restrictions about how many hours kids can work.

      • nolalola27

        The doll has a spit-up rag, too. That’s commitment to authenticity.

    • nolalola27

      To all the chicks worried about spoilers: It was 2 weeks ago. Don’t read an article which is clearly about Mad Men, after the finale, if you don’t want spoilers.

      Regarding his decision: Don’s mistresses are always the challenging, independent, brilliant women. He marries Betty & Megan. To be fair, though, Megan is a huge up-trade from the cruel, childish Betty. Also, he’s a work in progress. Also, he can’t stay close with anyone after they know the real Don Draper/Dick Whitman. Remember Anna (lived across the country and then the Big C)? Then he & Bets got the divorce after she found out, and so he had to call it splits w/Dr. Faye. So I get it. I’m just curious to see if she uses that information against him next season.

      • Amanda Chatel

        To quote Faye, when Don dumped her: “I hope she knows you only like the beginnings of things…” I’m no psychic, but I think that says a lot about the next season.