Ok a month ago I asked the question "would you date a co-worker"? The majority of the people said it depends, about a quarter said yes and just under 20% said I better find a new job.
Normally I don't post my private life but since the date was going to be a 3 day long trip to a large city 300 miles away, I wanted a little feedback. The trip went very well but here are some tips from my experience.
Tip 1:
No matter how much you prepare, after 72 hours together you will run out of things to talk about. Plan ahead but learn to deal with silence.
Tip 2:
Have a plan and a back up plan for every hour of every day. If something doesn't work out, you get lost, if you run late, she will end up staring at you wanting you to figure out what to do next. If you have nothing, you will look like a loser for dragging her 300 miles and have nothing planned. Driving in cirles, after a 300 mile drive is NOT acceptable.
Tip 3:
Even though you have never been to the location, you better know the directions and locations to every place you have a plan and a backup plan for. Trying to go out for a relaxing night at a local club when you can't and then you can't find the club, will blow everything. Luckily that didn't happen to me, I couldn't find the original club but I did find another one.
Tip 4:
DO NOT have your parents show up if at all possible! If they will also be there, plan with them when you will see them before the trip. That way you can plan "activities" around when your parents will show up and want to spend time with you.
Tip 5:
If this is your first date and it will last 3 days and you don't know the girl very well, do not be shocked if you find out she has major issues that go beyond the comprehension all people. I mean issues that go way, way past the average issue and start to resemble something you might find in a deep dark corner of the internet.
Tip 6:
Finally, have as much wild, crazy, taboo sex on the trip that you can. Then unless you two are a 100% match for each other, on the way home convince her that it would be best to end it now instead of dragging it out and risk having it get ugly at work. It's just better and easier that way.
With that said, the trip went very well. I still have my job and we still talk but nothing beyond that now. For those that want to know, YES I would do it again in a heart beat.