Gusto

I am not a master of the conversation. With people I know, whatever, it's no problem. But with people I don't know, I somehow always end up saying the exact wrong thing. Take for example, last week when I was doing staff ID pictures-

Person says to me: "Okay, now, I want to look thin and pretty in my picture"
What I say to them: "Everyone keeps asking for that, that's a lot of pressure"
What I meant: God knows. It was the first thing that came to mind.
What it sounded like: "You're fat and ugly."

Person says to me: "Try to make me not look pregnant in my picture"
What I say to them: "But you are pregnant." (WHY, GOD! WHY?!)
What I meant: She was pregnant. What do you want from me?
What it sounded like: "You look fat."

Or today, for instance:

Person says to me: "I need to pick up a student"
What I say to them: "Are you her grandmother?"
"No, I'm her mother"
What it sounded like: "You look old."

The point of all this is, I tell you what, I had a few minutes of pure genius conversationality this evening talking to the guy behind the counter at the coffee shop. It was like I was so on. I didn't call anyone fat or ugly. Coffee shop guy thought I was so funny. For a few minutes tonight, I wanted to be my own friend.
Here's how the conversation would have gone, had I decided to be my own friend:
Cool me: "Hey can I have a chai?"
Regular me: "Do you want that with skim?"
Cool me: "Nah."
Regular me: "Are you sure, whole milk is really bad for you. Oh, and by the way, you're fat and ugly. Let's just get that out of the way, cause at some point during the conversation. I'm going to unintentionally hint at it."
Cool me: "Cool."

As a side note, a student went into labor in my office today.