Ask TSJ: Digging on My Lady Boss

LIFE IS HARD. It seems like every new day brings a new question that, try as you might, you’re just unable to find an answer for. The Smoking Jacket understands this, and we’re here to help. TSJ’s editor, Melissa Bull, and Headshots columnist, Mike Spry, set aside some time in their busy schedules to answer your questions in a feature we’ve cleverly named “Ask TSJ.”

This week’s incredible question comes from a TSJ reader in Arizona.

I’m the tech help at my office, I’ve been there a while, and it’s a good gig. Here’s the thing, though –  have the hots for my lady boss. She’s like a big exec, but we’re always joking about Game of Thrones and we get McDonald’s together sometimes. She’s super hot. Should I make some moves?

- Lester, from Tulsa, Arizona


Hey friend,

I’m not going to say smoking lady boss doesn’t dig you, because I’m sure you are a fine catch and all, but as someone who is, like your lady boss, also a girl, I’ve got to say that dudes often misconstrue friendliness for interest in that way. Like, everyone jokes about Game of Thrones, and McDonald’s ain’t no four star resto. AKA if you wonder whether the McD’s excursions are dates or not the answer is not. Nope. Nyet on the date excursion.

I’m not saying a work love blossoming is impossible. And until the litigation, and maybe even after, or during? things could get steamy, thaz fo sho. But the fact she’s your boss and the fact you’re reading a lot into your water cooler convos makes me think you need to hop on the Let’s Date bandwagon and meet girlies from your neck of the woods. Or maybe from the mail room? Ya man.



Hey Lester,

You know, at first glance I thought you wrote, “Should I make some movies?” and I was all, “Hells to the yeah Les! Get your digital camera running and play a round of naughty tech dude meets S&M leathered up hot exec lady.” I got a little randy thinking of it. Then, I reread your letter and noticed that your query was about making moves. So, my suggestion to you is: MAKE SOME MOVIES! That’s your move, dude. THAT. IS. YOUR. MOVE.

Given that you’re a tech guy, I’m guessing you’ve got some good equipment, and lady boss wants your equipment, and so the two of you should make some low budget features using all of the equipment.

Also, lay off the Mickey D’s. Seriously.

- Mike

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Ask TSJ: Doing the Barista
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Ask TSJ: I Want to Ask My Receptionist Out