Kate gets encouragement on her singing career on This Is Us. "Number Two" is the ninth episode of the show's second season.

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NBC
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This Is Us
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This Is Us Season 2 Episode 9: "Number Two"
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Los Angeles, CA
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This Is Us Season 2 Episode 9 Quotes

Toby: I am a large and powerful man. And on most days my stature is only a compliment to my sharp, comedic wit. But today, I am a man with a fiancee who has had a terrible last twelve hours. Right now, she's somewhere in a red dress singing in the middle of the day because she can't face how awful she feels. And that breaks my heart. So I'm not feeling all that funny.
Carl: It's nothing personal... (voice trails away)
Toby: The hardest part, Carl, about seeing someone in pain, is not being able to do anything about it except try not to make it worse, which brings me here to intercept a package that if were to arrive on our doorstep would most certainly make it worse. I am a large and powerful man Carl and I don't know how much longer I can stay this calm.

Kate: I feel like I failed you.
Toby: You didn't. You never could.
Kate: I want to try again. Not yet. But maybe soon.
Toby: Yeah, me too. Whenever your ready.