Debra Jo Rupp guest starred on Friends as the much older girlfriend of Phoebe's half-brother, Frank Jr. (Giovanni Ribisi).

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Friends
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Friends Season 3 Episode 18: "The One with the Hypnosis Tape"
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Friends Season 3 Episode 18 Quotes

Phoebe: So, how was your day?
Frank: Oh, well just probably the worst one since I've been alive.
Phoebe: What, mm, what happened?
Frank: Um, Alice, ah, she, ah, called it off.
Phoebe: Oh no. Did, um, did she say why?
Frank: Uh, no, not really, just that I was too young, you know. But I don't see how I could all of the sudden be too young, 'cause I'm older than I was when we first got together.

Rachel: (About Pete's tip) Oh, my God. I can't believe this is a real $20,000 check. Oh, this is just so exciting.
Monica: Or incredibly offensive.
Rachel: Oh yeah, sure, that too.