Bachelorette Pt. 2 - Date Planning

Part 1

Of course I said yes to this without an actual date idea.  First dates are always tricky.   You know very little about the person so it's hard to personalize the date.  I generally like to plan a first date where we will have a good time even if either of us realize fairly soon in there isn't going to be another date.

My plan was to treat this as best I could as a real first date.  Ignore all the odd surrounding circumstances and move forward.  My goals going in were to do something representative of what I would do on a date, but not necessarily as a first date, get some honest feedback for future use, and have fun in the process.

So what did I know about Sarah at this point that I could use for a date idea.  Not much really.  We both mentioned that in online dating you really need some form of intelligence test before someone can message you.  I knew she loved comedy, especially ComedySportz.  When she told me about being an audience volunteer in a CSz show her eyes lit up like my nephew's does when he tells me what Santa brought him.   Then a stroke of genius hit me.  Ok, one of my improv buddies had the idea.  Her idea “Shoot, you should make use of the experiment for your own blog. You could play a few games like Pavlovian Response – every time she says the word ‘blog’ cluck like a chicken.”  So the idea was to take a few of my favorite games to perform and turn them into a long form improv date. 

The basic premise was to have an improv themed “scavenger hunt” date, throw some first date questions into a hat to keep the conversation going, and do something total goofy along the way.   Note:  This is where you really have to calibrate and cater to the specific person you are going out with.  I know several of my female friends if someone asked them to do anything (or specific subsets) you are about to read they would be absolutely horrified.  From the little interaction I had with Sarah up until this point I was pretty confident she would love it unless the execution went horribly wrong.  I should also note this was the first time I have ever tried something like this.  I’ve thought about the general scavenger hunt idea before, but never dated anyone I thought would enjoy it. I sent the following Evite for the date to Sarah.  Now I actually had to figure out the places we would go.

I designed the scavenger hunt for dinner and improv show.   Each place would have a clue (and hint) as to the next location.  The dinner would be at a BYOB restaurant so we would have to stop by and pick up some wine.  The logistics were tough.  The show started at 7:30.  With dinner and a couple stops along the way, we would have to start the date fairly early.  The other hard part in planning was the end.  The show would end between 9 and 9:30.  I’m pretty sure not many women on their kid free weekend want to be sitting at home on a Saturday night at ten o’clock, no matter how great a time they had earlier.  Originally, I had added a dessert stop for after the show but cut it out for fear of feeling the date was too long.  I figured it was better to err on the side of her wishing we had spent more time together, than wishing the date would hurry up and be over.  Also, I could always suggest doing something afterwards if we were having fun.

My blind lines were normal first/second date questions.  Knowing my improv friends would have some funny/outrageous suggestions I asked for their input and took the following to add into my 25 or so lines.

•  So I know where to aim, which part of your body is the most ticklish?
• I secretly use to be ______
• Ribet, ribet, ribet is the sound I make when ____
•  I'll be off probation soon, I can’t believe they caught me doing ______
•  I was dumpster diving the other day and I can’t believe I found ________
•  Do you put out

I'm sure you can only imagine the ones I rejected.

My Pavlovian response was that I would cluck like a chicken anytime she mentioned her blog.  I honestly figured she'd mention it within the first minutes of the date as we would both be writing about the date.  I had my friend Jamie send Sarah a couple suggestions for hers knowing she would keep them first date appropriate.  Sorry guys I know the kind of things ya’ll would have suggested.  



Part 3
Part 4