ASK SASSY: Office Flirtation
Dear Sassy,
I’m in love with the girl in the next cubicle. I think she likes me too. We talked about Lost at the copier and she’s really pretty. I think she even knows my name. Should I pursue her?
From,
The Man with the Red Swingline
Dear Swingline,
Ah…my friend… you have chosen to fall in love with a young lady in an arena fraught with lawsuits and awkwardness. You’re going to need to tread softly before dipping your pen in the company ink, as it were. We have that whole sexual harassment thing to think of, and we must be very, very careful. Sassy is always down with some copy room necking, but she’s not about making innocent young ladies feel uncomfortable in their working environment.
Personally, I do not advocate asking your special lady friend out in the office. Do some reconnaissance. Does she enjoy martinis and mini cheeseburgers at Pacific Grill? Dancing on the bar and smashing Bud Light cans on her forehead at Cans? Find out where she goes to relax, bump into her there, and make your move.
Now, if you are a shy guy, you can try the soft start to the process. It’s called the Craigslist “Missed Connections” section. Sample ad:
YOU MAKE WORKING AT TOPIA TECH BEARABLE mfw 34 (Tacoma)
Susan,
We work together at Topia Technologies and I think you’re the bomb. When we discussed the subtleties of the Jack/Kate/Sawyer love triangle on LOST I couldn’t help but wonder if you would want to kiss in the rain after we narrowly escaped being killed by the polar bear. The season premier is coming up in a week, and I would love to watch it with you…
Sincerely,
Your Cubicle Castaway
Now some of our more critical readers might scoff at my recommending Missed Connections, but since this is the workplace and the judicial system could be called into play if it turns out you are a creep, I really recommend giving that a shot first.
Good luck my Swinglining friend, you will probably need it.
Love,
Sassy
Recommended Reading: The Game by Neil Strauss
FULL DISCLOSURE: Sassy thinks Neil Strauss is a tool.
Recommended Listening: Can’t Take My Eyes Off You by Frankie Valli
Got a question for Sassy? Send it to asksassy@exit133.com
6 comments
H holden January 24, 2008
a red swingline is a total turn-on . . . almost as exciting as a notary embosser
D Daniel Blue January 24, 2008
i think he should post a memo to the whole office proclaiming his intention to date, requesting the bosses (and maybe her father’s) permission.
i suggest a different show…however, lost is the kind of thing you can really loose yourself in.
M Mofo from the Hood January 24, 2008
Mr. Swingline:
Rule #1: Never ask a woman advice about another woman (see Sassy above).
You need to close this deal fast or you’re gonna end up in the friend bin.
Mofo’s Fastrack Program: aka Hit it. Hit it. Quit it.
Tomorrow at work tell your next target, I mean potential girlfriend, that you’re gonna grab a beer after work and that she should join you. Simple. I trust that you know what to do after that.
P.S.: Don’t stare at her like a goof who just saw his first rainbow.
C Certified Smarty Pants January 25, 2008
<GASP>!
Mofo, I cannot BELIEVE you are discrediting Sassy’s heaven-sent advice! As a lady myself, I think her advice shows the wisdom of the ages. And personally, I love being looked at like I am someone’s first rainbow.
Mr. Swingline, I urgently plead with you to disregard Mr. Mofo’s advice lest you desire a sexual harrassment suit and an office full of icy women who will be more than happy to make your life a living hell.
M Mofo from the Hood January 25, 2008
Ms. Smarty Pants:
I’m thinkin’ that you need a good swat in a very important place.
C Certified Smarty Pants January 25, 2008
Mr. Mofo,
Hey, I just calls ‘em as I see ‘em. Don’t hate the playa’, hate the game.