Played by: Lynn Clark
Appears in The Stake Out & The Stock Tip
Jerry meets Vanessa while attending a dinner party with Elaine. Jerry learns that she works at a Law Firm called ‘Simon, Bennett, Robbins, Oppenheim and Taft’, and decides to stake out her office to ask her out. After dating for a short time Jerry takes her to a bed and breakfast in Vermont but rainy weather keeps them inside and ruins the whole trip. Jerry should have listened to George, who advised against the weekend get-away calling it a ‘dating decathlon’.
Vanessa: How big a tip do you think it’d take to get him to stop?
Jerry: I’m in for five…
Vanessa: I’ll supply the hat.
Jerry: Uh-oh… What do we have here…
Vanessa: Why don’t you relax and take your jacket off?
Jerry: Oh, I can’t– I have a tendency to get chilly.
Vanessa: How masculine…
Jerry: Plus I’m wearing short sleeves, I don’t want to expose my tattoos.
Jerry: So, you’re a lawyer…
Vanessa: Sagman, Bennet, Robbins, Oppenheim and Taft.
Jerry: [To himself, quickly] Sagman, Bennet, Robbins, Oppenheim and Taft…Sagman, Bennet, Robbins, Oppenheim and Taft…
Jerry: [To Vanessa] Of course, they handled my tattoo removal lawsuit!
Vanessa: Oh, that was you!
Jerry: Imagine, spelling “Mom” with two O’s…
Vanessa: Very funny! What do you do?
Vanessa: Really… That explains it…
Jerry: Hey, hey… Pamela’s birthday party, didn’t I see you there…Jerry.
Vanessa: Sure! Hi!
Jerry: This is George. I’m sorry…
George: Nice to meet you.
Jerry: Ah, Sagman, Bennet, Robbins, Oppenheim and Taft.
Vanessa: That’s right! What’re you doing here?
Jerry: Oh, were meeting a friend of ours for lunch. He works here in the building.
George: Yeah, Art Vandelay.
Vanessa: Really? Which company?
Jerry: I don’t know. He’s an importer.
George: …And exporter.
Jerry: He’s an importer/exporter.
George: I’m, uh, I’m an architect.
Vanessa: Really. What do you design?
George: Uh, railroads, uh…
Vanessa: I thought engineers do that.
George: They can…
Jerry: Y’know I’m sorry you had to leave so early the other night.
Vanessa: Oh, me too. My cousin had to go back to Boston.
Jerry: Oh, that guy was your *cousin*!
Vanessa: Yeah, and that woman was your–
George: I’ll just, uh, get a paper…
Jerry: So, um, do you date immature men?
Vanessa: Almost exclusively…
Jerry: I have to say. Those people talking behind us really ruined that movie for me.
Vanessa: Why didn’t you do something?
Jerry: What do you want me to do? I have the guy the half-turn. Then I have him the full-turn with the eye roll! I mean, beyond that, I’m risking a punch in the mouth
Jerry: Have you thought any more about that trip?
Vanessa: Yeah, I’ve been thinking about it.
Jerry: You know, my friend told me about this great place in Vermont.
Vanessa: I don’t know. I just worry about trips like this.. It’s a lot of pressure.
Jerry: It’s great! It speeds up the intimacy level. It’s like putting the relationship in a time compressor. Where we would be six months from now we accomplish (snaps) three days.
Vanessa: Oh, so you want to move our relationship into Phase Two..?
Jerry: Exactly. I love Phase Two. Extra toothbrushes, increased call frequency, walking around naked.. You know, the presents get a lot better in Phase Two.
Vanessa: (Starting to like the idea) Really? Could we go fishing up there?
Jerry: Yeah. We can fish. What? Blues, carp, marlin?
Vanessa: They have marlin in Vermont?
Jerry: Oh, big fighting marlin.
Jerry: What kind of perfume is that you’re wearing?
Vanessa: Oh, you’ve never heard of it.
Jerry: No, what? What kind is it?
Vanessa: I can’t tell you.
Jerry: (To himself) Yeah, that’s normal.