Interestingly enough, my most memorable dates did not involve me as the "Dater" or Datee", but yet simply the facilitator.
This was about 12 years ago. My roomate and best friend had the hots for a certain Palestinian girl whom he met whilst working at a certain retail shop.
Now, problem is, my friend was about as romantic as a wet sock, so be begged me for help to win her over.
Being the guy that I am, I readily agreed to help, and both of us set out to win her hand for him like a Military campaign.
The first item was to separate the dates into a "series of dates" in which each would have a theme, to show the various sides of him.
These theme dates were separated into:
The Poet
Curly the stooge
The Warrior
The intellectual
"The Poet Date" consisted of choosing a natural hilltop on the outskirts of L.A. primarily for it's great sunset view.
In advance, I had prepared a picnic basket, guitar music, wine and cheeses, etc, and of course, a book of poetry. I choose a mixed author. The trick was of course, to set this up in a short time without someone walking by and stealing/messing up the setting, but also not to be seen, in order to provide my friend with 100% credit for the act.
I chose to wait on an adjacent mountain at a prescribed time, and after setting up the picnic, await their arrival up the mountain and then, since there was only one path down, "Pose" as a jogger, completing my disguise with set of headphones, sweatbands, and shorts. It went off without a hitch, and she was none the wiser.
Dress: Linen Dress Shirt, Khaki Shorts, for that "Hemmingway" look.
The Curly Date: This date revolved around one object and one object only. To be as silly as possible, and to make her laugh until she puked.
The date started off at a local Sundae Shoppe, and my friend ordered the largest one they had (The kind you get a prize for if you eat it all.) We had planned in advance, a lot of funny, (if not corny) jokes to be told, confetti to be thrown, and it was mandatory that he wear most of the Sundae rather than eat it. We also planned several magic tricks, and one of them involving the "old magically appearing coin" trick,
but the twist was, we used an old Greek coin, and had her name inscribed upon it beforehand.
The second phase was to take her mini golfing, and my friend was to purposefully manage wild swings, funny comments about the other players, and of course, an "accidental slip" into the course water hazard. The result was that reportedly she peed her pants from laughing so hard.
DRESS: A T-shirt with "Curly", purple pants, and a Goofy Cat in the Hat Party Hat.
The Warrior Date:
This one is, as it states, to show the "Warrior Side" of my friend. At the time, I had introduced my friend to the Dojo I was training at, and although he was only a white belt, since I was the Senpai for the evening, I made certain that the class she was chosen to "Observe" was most hardcore, and that in our sparring sessions, I let my friend get the best of me.
The evening was followed by a trip to a local Biker bar, (Though this one was frequented by weekend warrior bikers, who were mostly CPAs, Lawyers and Doctors, so the danger factor was quite minimal.)
DRESS: Leather Jacket, T-shirt, Biker boots, Chain Wallet.
The intellectual Date:
This one was the most simple of all.
Museum Row, followed by a Restaurant which allows Wine Tasting, and the an evening at the Observatory.
DRESS: Tie and Jacket.
Good Stuff.
I was the best man of my friend and his wife at their wedding 6 months later, (This was 10 years ago.) and they currently are still married, and have twin sons.
There's a bit of Metablade in all of us.
