Online Pimp... a true story.

(DISCLAIMER: This was when I was young, stupid and it was BEFORE Maddilicious was part of Team Chaney. )

If you asked me five years what my new job was, I would’ve simply mumbled, “administrative assistant” and changed the subject. Because no one knew that the only assisting I was doing was assisting my boss, *Scott, meet chicks online.

I was an online pimp and this is my story.

I met Scott when I interviewed for this alleged “administrative assistant” position. The good news, I got the job right away. The bad news, he wasn’t really looking for an assistant. He actually wanted to take a crack at dating online. Scott had tried himself a few times, but these “stinkin’ high maintenance women” actually wanted to "GET TO KNOW EACH OTHER" before meeting in person! Scott didn’t have the attention span to sit at his computer for more than ten minutes. This is where I come into his master plan. I accepted the job because I had just recently been laid off and needed to work right away plus he told me I could work from home (working in pajamas? SCHWEET!). I accepted his offer, not fully realizing what I was getting into.
On paper, Scott didn’t seem like a bad catch. He was a successful businessman, made tons of money, owned two homes and wasn’t completely horrible to look at. Sure, his hair looked as if he just rolled out of bed thirty years ago and never bothered to comb it since and his suit always seemed lopsided somehow, but put it all together with his goofy grin and naturally slurred speech (think Anna Nicole) he was kind of endearing, like a three legged puppy. Armed with his personal information, his photos and criteria for what type of women he was looking for (mid twenties, early thirties, blonde and breathing.) I was prepped and ready to go. I signed him up on fifteen online dating services and started searching for potential dates (unsuspecting “Johns”) for Scott (my bitch). I was to pose as Scott online and keep a correspondence with these women until they were willing to meet him in person. Easy enough right? Not quite.
I immediately started getting responses from women who were interested. It was scary how easy it was to pick up women online and even scarier still how willing they were to invite some STRANGER (in this case, unbeknownst to them, a married woman!) over for dinner at their place! I collected phone numbers, saved chats online and kept a record of each woman’s personal bio and pictures. It was organized in such a way that when Scott had to talk to them on the phone, he picked up where I left off…. Or at least, that was the plan.
Unfortunately, poor Scott really didn’t pick up where I left off. While the ladies loved talking to the Scott online (me)… they were baffled when they finally spoke to Scott on the phone. I got a glimpse of his social handicap when Scott put me on three-way call when he contacted one of the ladies I had been chatting with. He decided to call a potential date that wanted to meet him as well as bake him cookies. It was disastrous... ..and he only spoke with her answering machine! He began the message simply enough,

“Hi *Jennifer, this is Scott from the Internet?”

Then the message took a sharp left turn into Wierdsville.
“Umm, I look forward to your chocolate chip cookies … I love cookies. (Jennifer had made a mention online about baking him cookies so this was his "witty" attempt to work it into the message) Especially when they are hot right out of the oven, huh.. huh.. huh..!"

The term "right out of the oven" took on a perverty old man quality because of his inane, almost crazy, giggling. It wouldn’t have been so bad I guess, but it was VERY obvious he was reading it right off an online chat I had with her that he printed out. I could even HEAR him shuffling the papers! I was mortified. I had hoped he would wrap it up and just say good-bye but, like the Energizer bunny, he kept going and going and going ...

“I love cookies. Oh, I think I said that, huh huh! I look forward to meeting you. I will call you back. Umm this is Scott, if I hadn’t mentioned that already.” I’m so sorry you’re not home."

It started to sound like a bad Dick & Jane book. But Casanova kept at it.

“My phone number is 555-5555. I really want to get together sometime. Umm … take care … have a great day … talk to you later … bye, bye.”

After he hung up, I was ready to console him, to tell him it wasn’t “that bad” and that he’d do a better job at talking to her one on one. Except, I didn’t need to console him because he thought he did a damn great job, especially that “oh so clever” line about the cookies! This date was in the bag for sure!
He was giddy.
I was speechless.
Getting him a date was going to be harder than I thought. Scott didn’t seem to understand the simple give and take process that takes place in a conversation between two adult people. He was so busy “trying” to have a conversation and figuring out what to say next, that he didn’t have time to pay attention to what the other person was saying. This resulted in pointless conversational banter that was usually a one-man show. (Starring SCOTT!!) I even tried to set him up with my single friend who had a soft spot for oddballs like him. Even she was taken aback by their conversation. He called her on his cell phone while driving around with his buddy. During this conversation, he was also giving directions to his buddy with absolutely no change of tone in his voice. As a result, she didn’t know whether he was talking to her or his friend.

“Hi Desi, how are you? Turn left. I’m glad to finally get to talk to you after all our online conversations. Sharp right here, see that church over there? Yeah right there. So are you there? Left again over here. Desi? Do you want to go out to dinner sometime? okay, pull into the parking lot.”

Desi was speechless.

She never called back. In fact, none of the girls he called ever called back. I started getting rejection emails from them right after they spoke to him on the phone. I had to change my tactics. I decided to bypass the phone number and go straight for the jugular and ask them to meet for coffee. Maybe, just maybe, Scott would fare better in person. Hopefully the “poor but lovable, three-legged puppy vibe” he exuded would win over some girls. I invited every girl I had been chatting/emailing online to go out and surprisingly, I had a few takers! Scott on the other hand, was a different story. For a guy who wanted to go on dates, he sure went out of his way to avoid going! The first date was to take place at a coffee shop and he knew three days in advance that this date was scheduled. I got a call from him two hours before the date, informing me that he couldn’t make it because he was at Disneyland (mind you, he lived in San Diego which was roughly about two hours away from Disneyland!) He didn’t plan on going to Disneyland but YET, there he was! To this day, I didn’t understand his explanation on how he got to Disneyland; but he appeared to be as surprised as I was that he was there, as if he was bagged and gagged by Mickey himself. Scott wanted me to call him back with his date’s phone number so he could break off the date. Upon calling him back, he REFUSED to answer his phone! I didn’t want this poor woman to be stood up at the coffee shop, so I posed as his personal secretary and called off the date myself. I was infuriated!
I began to wonder exactly what his intentions were when he cancelled date after date with lame excuses like “unexpected work” or “car problems”. I’m surprised he didn’t throw in “cramps” or “bad hair day” as an excuse too. It went downhill from there. I got snippy with him on the phone when he blamed ME for his lack of dates. I kept asking him what he wanted but in the end, he was as lost as I was.
His last ditch attempt to email EVERY GIRL on each website to see who answers, was the last straw for me. I couldn’t, in good conscience, set up normal women looking for love with Scott. I got to know him in those few weeks and in my humble opinion, he didn’t need an online dating pimp, he really needed some good ol’ fashioned therapy. Throw in a few classes on socializing with HUMAN BEINGS and he’d be golden! But alas! I am not a therapist and I didn’t have enough patience or the superpowers to teach Scott how to be a smooth.
So after a month and a half, I hung up my hat and said goodbye to my shady pimping past.

Sometimes, when I see The Anna Nicole show or a bad hairpiece, I think of Scott and wonder if he ever found love. Despite his odd ways, I believe he was a nice guy who just didn’t have a clue. I wish him the best, wherever he is, and I really hope he’s found someone like himself to have long pointless conversations and who’s up for spontaneous trips to Disneyland.