NOTE: The following post is intended as instructional and constructive advice. This is NOT intended to discourage boys and girls from asking out other boys and girls. This is just a friendly reminder to, as we say in the biz, check yourself before you wreck yourself.
What happens when you meet someone really fly and adorable through work, but you don’t want to make a wrong move? You have to tread lightly, right? You have to watch what you say lest you embarass yourself/your company.
Below are some actual emails to my roommate in which only the names have been changed. Read/judge for yourself. You know you want to. (Items in italics added by me.)
—–Original Message—–
From: Geronimo Snacks
Sent: Thursday, February 14, 2008 4:19 PM
To: Nellie Salty
Subject: Happy Thursday..
Hello Nellie..
Hmph. You should know that I am very rarely so bold, but perhaps as a result of particular date, I’m a bit more amorous than usual… (Smile.) Then again, I suppose the only real difference between what I’m doing now and what I would have done instead, is not waiting a few days before asking mundane thing to Your Company (perhaps to confirm the exact website address, or whether or whether or not you guys allow interns from Canada(!)). At some point, however, I’d have to ask my real question anyway..
I like how right away he evokes a grumbly old man. He’s thinking, hey, if Walter Mathieu can get Anne Bancroft then I TOTALLY have a shot with Nellie Salty. He is a very visual writer, alright. (Smile.) These dot dot dots! I’m so anxious to know what his real question is…
Of course you know virtually nothing about me, except where I work, and that soon we will have a German intern. Well, you also know that I’ve done a bit of traveling, and if possible would love to make a lifestyle out of it for a while. But for now, I’m rooted on by Long Beach and NYC.
So anyway, therefore I send my humble invitation for conversation including tea or coffee sometime. Surely you have a few stories and perspectives from living overseas for six years which I would very much love to hear about. Likewise, if you are interested in the nuances of solar power, or learning about first hand behavior of penguins in Antarctica (one of many sea stories), perhaps I can help. OK. I AM actually interested in both those things. But I’m not Nellie. But, seriously, don’t worry either way. If nothing else, it’s really just an invitation to say hello in a different context. (BTW, are you stuck in this evening - you are welcome to call?)
Be well Nellie. Welcome back to the US.
Yours,
Geronimo
Geronimo Dennis Snacks, PE
SomeCompany CES LLC, CTO
All in all, not a terrible way to broach a very awkward subject. Inappropriate, yes. I think maybe he took some Valentine’s poppers and his love butt hole was flapping open in the breeze and beyond his control.
—–Original Message—–
From: Nellie Salty
Sent: Thursday, February 14, 2008 5:37 PM
To: Geronimo Snacks
Subject: RE: Happy Thursday..
Hi Geronimo,
Thank you for the email- quite a surprise, actually! I do indeed have plans for the evening, but thank you for the invitation. I am sure that you have many fascinating stories to share and I am quite impressed with your field of work. M_ is lucky to have landed such an interesting internship.
If you really do want to know what our web address is, it’s: http://something.net/ and yes, we do accept interns from Canada through our Professional Development Program.
Best regards,
Nellie
And if someone responds in a totally professional way that’s a pretty sure fire sign that they’re, um, what’s the phrase? Just not that into you. Check.
—–Original Message—–
From: Geronimo Snacks
Sent: Monday, February 18, 2008 10:30 PM
To: Nellie Salty
Subject: RE: Happy Thursday..
Hello Nellie!
I smile. I kid, I kid. No worries. Oh yes, and thanks for the information (he). This part makes me sad. It probably wouldn’t have been like that in a giggle in real life, but the parentheses chuckle makes me feel anxious.
Please don’t be surprised. The fact is, there are not many smart, well traveled, adventurous, and incredibly beautiful & tall women out there..! I know, I’ve been looking for a at least - my lifetime; the opportunities to meet them are far and few in between. Oooh, how raw does that next line make you feel? I know Nellie, and she is totally all of those things. But that’s just not the way to do it!
Honestly, it was rather uncharacteristic of me, but it being Valentines Day and all, I figured I’d try. We come to: “It being Valentines Day and all…” That is going to be my excuse when I try to storm the White House on July 14th. Officer, it being Bastille Day and all, I figured I’d try. What’s the problem?
So anyway, I look forward to having M_ on the Some Company team for a while. If anything else comes up, for you or A_, please don’t hesitate to contact us.
Sincere Regards,
Geronimo
(Ps - And yes, the invitation still stands. :o)
OK, so that’s the end. I know that you probably think I’m a terrible person for posting this. But that’s what happens! Nellie wanted me to. She wanted all the Geronimos out there to know that this is NOT the way into a smart, well traveled, adventurous, incredibly beautiful and TALL woman’s heart!
Take note, people. Sometimes the meanest advice is the best advice.

You know what would be great? If Geronimo Dennis Snacks was really short. Like 24 inches. Like mini me.
Also, did you choose “Nellie” as the protective pseudonym of your rommate because her allowing you to post these emails parallels the villainous behavior of a young Nellie Oleson?
You guys are crazy. What could be more romantic than asking out a work-related acquaintance over e-mail and professing your physical attraction to her before you’ve been on one date? That takes guts.
p.s. - Yes, in case you were wondering (and I know you are), even though you’ve humiliated me in front of the whole blogosphere, my invitation still stands. :o)
hmm… how about being more casual. Seemed to business than personal. If its seems like your going to a business meeting than anything by the tone of your voice its not very appealing to start out with. Try going with a friend kind of tone. The whole letter seemed to me that it was more like business than personal…