"Can you make up a social calendar for me?"

"I want to know where all the cool stuff is happening...you know, like on the West Side and stuff."

OK. Not only do I do all of Bossman's errands for him, pay his bills, and make sure that his dog doesn't die from plaster inhalation*, but now, I have to tell him where to go have fun. There are a number of blazing obstacles in the way of successfully fulfilling this request. These obstacles led me to compare the social interactions of my boss and I.

1. Bossman's interpretation of "something cool/fun to do" is obviously slightly different than mine. I have friends that I go out with and have fun simply as a result of how cool we are collectively. One of my recent trips to Boston for example:

Doesn't this look like fun?

Bossman invites people over to eat sushi off of mostly naked girls. One of his recent parties for example:

note: The interview process for finding these girls was really very interesting

2. If I'm going to a cool event, would I really want to have Bossman there with me? Would you want your boss there? Keep in mind that he is only 5 years older than me and Providence is a small town so it's not such a stretch that we would see eachother out socially. However, the facts that he doesn't like to tell people that he has an assistant, never gives me credit for anything, and ignores me when I see him out and about, make me less inclined to make him in with my kind of in-crowd**

3. Most of the time when I go out, fun finds me. This isn't a conceited statement. One rarely makes specific plans to go out and do something that cool people do. It's a trial and error thing. You go out to a restaurant that someone has heard good things about and they turn out to have a really good bar scene. You go to an outdoor concert and stumble upon a goth marching band from Brooklyn. As I get older, I'm convinced that "cool" is a very organic thing. You go to a party and it just happens. My Christmas party for example:


Trying too hard leads you to a birthday party where everyone gets embarrassed by the bellydancer:

note: See how the only people watching are the waitress and the bellydancer's escort? Everyone else has their back turned. Weirdos.

What did I do in the end you ask? Well, I did my best to compile a combination of the invitations he had received, art gallery shows I thought he would like, and recurring events at local bars (e.g. the very cool salsa night that I have actually attended. See? I'm able to share). I sent it in a very organized spreadsheet and asked him to give me some sort of direction towards what types of events appeal to him. Obviously unimpressed, he's now sending me links to websites that may "be a good source for my social calendar."

This man is like Pandora's box. Every request leads to a thousand more questions about him. If he knows about these websites then why doesn't he come up with his own social calendar? Who is so busy that they can't figure out how they'd like to spend their free time? Certainly not someone who has a PA to do almost everything for them. Why won't he just admit that he's having trouble meeting girls instead of coming up with this cockamamie story about wanting to expand his social sphere and do "cool stuff?" Exasperation is my middle name.

*We had a shower valve crack and leak water into the kitchen. As a result, a large patch had to be put in the kitchen ceiling and it was determined that the dog either really wanted to help with the construction, or, had a hankering for white powder lying around (much like most of Providence's East Side).

**Not that I'm some sort of hipster. I wouldn't know what the in-crowd was if they poked me in the eye with an escargot fork.