The Co-Worker Dilemma

[just_a_fish]

I'm well aware of the old adage "don't %$%# where you eat." But in this case, I think there are some circumstances that can allow that rule to be relaxed somewhat.

 

First (and most importantly), it isn't prohibited by our company bylaws. Only a supervisory relationship or a situation that creates a clear "conflict of interest" is prohibited. Neither exist.

 

Some quick background: I worked with her for 2 1/2 years before she got another job within the company that required her to move to another building. But due to the nature of our work, we still exchange occasional calls and e-mails, although nowhere near as often as before. They've always been professional in nature.

 

Last week, she called the office to get some needed information from me. She said that she would be in town the next day and wanted to get the old office gang together for lunch. Unfortunately, I had to turn it down due to having a client appointment.

 

We're roughly the same age and she's a very attractive (and single) young lady that gets along with 98% of us. I've been considering asking her on a date for about a month now - although I certainly have no guarantee of being taken up on the offer.

 

My challenge boils down to 2 different areas - finding a place to ask her AND going for casual lunch and/or the all-out dinner. I'm more inclined to throw the "Hail Mary" and try dinner since my face-to-face interactions with her are so infrequent now.

 

Although I have more than my fair share of nerves, e-mail and Facebook are weak and are obviously out. The phone isn't much better. There aren't any more opportunities to spend time with her that could be spun as a "group project lunch." More or less, I have to stumble into a way to cross paths with her outside of a work environment and roll the dice there.

 

If I fail, it will be "one and done." The matter won't be pushed and I'm fairly confident we can continue to treat each other as colleagues.

 

Am I crazy? Any thoughts that could improve this plan?

[welikeincrowds]

The phone isn't much better.

 

Why not?

 

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[just_a_fish]

Simply because I don't have her cell phone number, and a call to home (which I also don't have) can place her on the defensive from the very beginning. It's far easier to shoot somedown down over the phone than in a face-to-face conversation.

 

Also, I'd rather not call her office in the heat of the workday and trigger a possible, immediate post-mortem reaction for everyone to see. Conversations are clearly audible and whether positive or negative, the results can spread quickly.

 

An outside "buffer" environment is absolutely necessary in this situation. At worst, she gets a night to sleep it off and the option to keep the result private and out of the office.

 

While the argument can be made that "if she likes you, she won't care how you initiate the contact," she's still a co-worker and I have to make sure ALL my bases are covered at the end of the day.