(Author's Note)
In the episode, "Season 5, Episode 9 : Emily says 'Hello'". Emily calls Lorelai in a panic after saying hello to Simon McClan at the club. Here's the chapter about how all of that might have gone down.
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(No one's POV)
Emily is driving to hers and Richard's country club, determined to get out in public again, which she was hesitate about doing after that police report about her and Richard in the police blotter - which would mean that pretty much all of Hartford society would know that Richard and Emily separated after that Floyd and Jason fiasco.
Emily finally got to the club, and walked up to the first single man that she saw and said hello to him.
"Hi", she said.
"I'm Simon", he said, forwardly.
"I'm Emily Gilmore". She said. She figured of he was going to be forward with her then of was alright for her to be forward with him.
"Simon McClan", He said, introducing himself. "Emily Gilmore", he said to himself, "Oh she might be Richard's wife". He had always had the eyes for her for a while, but he was Richard's business associate and friend, so he hadn't done anything about it. Since he found out about Emily's and Richard's separation, he thought he would go ahead to ask her out, when he had a chance.
"So, this might be a little forward, and it's okay if the answer is no, but would it be okay if I was, to ask you out to dinner one night, say tonight" Simon said, nervously.
Emily was so surprised that she had taken Lorelai's advice about how to met another man, and if had worked. Since she was taking a while being so shocked, she jumped a little when Simon interrupted her thoughts.
"Emily, you okay", he said, interrupting her contemplation.
"Yes, I am, yes tonight would be great", she said.
"Okay, great, will pick you up in about 4 hours"?
"Sounds great, oh, I am in a run though", Emily said and walked away from Simon. When she got out of earshot, she hightailed it to her car and rushed home.
When she got home, she rushed upstairs, ran into Richard's and her room, up to her closet and threw it open. She then tore through her closet looking for something to wear.
"Maybe I should call Lorelai" She thought. "After all, it was her idea that I say hello to Simon, and then I will guilt trip her into coming here to help me", she thought and then she threw all of her clothes on her room and got the phone.
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~Author's Note~
Now, I don't know what Emily's thought process is, but I could imagine that is what she was thinking.
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