Katherine Parker: Ugh! What a slob.
Tess McGill: You were so smooth with him.
Katherine Parker: Never burn bridges. Today's junior prick, tomorrow's senior partner.
Alice Baxter: Maybe now would be a good time to go over what you expect of me.
Tess McGill: I expect you to call me Tess. I don't expect you to fetch me coffee unless you're getting some for yourself. And the rest we'll just make up as we go along.
Katharine Parker: The way I look at it, you are my link with the outside world. People's impression of me starts with you. You're accurate and punctual and you never make a promise you can't keep.
Cyn: Sometimes I sing and dance around the house in my underwear. Doesn't make me Madonna. Never will.
Katherine Parker: Never burn bridges. Today's junior prick, tomorrow's senior partner.
Tess McGill: What if he doesn't?.. pop the question?
Katherine Parker: I really don't think that's a variable. We're in the same city now, I've indicated that I'm receptive to an offer, I've cleared the month of June... and I am, after all, me.
Tess McGill: Oh god - and last night.
Cyn: Yeah, I shouldda checked the milligrams. Live and learn.
Cynthia: Whaddya need speech class for, ya talk fine.
Cynthia: Can I get ya anything? Coffee? Tea? Me?
Jack Trainer: Oren Trask? The man who said, "What if we sliced the bread before we sold it?"
Jack Trainer: You're the first woman I've seen at one of these things that dresses like a woman, not like a woman thinks a man would dress if he was a woman.
Tess McGill: Thank you I guess.
Tess McGill: I am not steak. You can't just order me.
Tess McGill: Bob, you're not seriously looking for a new assistant, are you?
Bob Speck: Well, not exactly at this moment, but I'm always on the lookout for new blood.
Tess McGill: I'm hungry, Bob, but I am not that hungry.
Katherine Parker: Dress shabbily, they notice the dress. Dress impeccably, they notice the woman - Coco Chanel.
Tess McGill: You know, maybe I just don't like you.
Jack Trainer: Me? Naaah.
Answer: It is also stated in the movie that Katherine just transferred down from Boston, and she is staying at her parents house. She also mentions in another scene that her and Jack are now in the same city. Plus Tess helps plan her welcome party to get to know others in her department indicating that she is new there. Maybe Jack had not got a chance to visit her office yet, which would explain why he would not have known.