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Law-abiding and tame, Larry's upper-crust upbringing tends to keep him timid in comparison to much of the series' violent, sexual, and other prison-related issues shown. He is also very sweet, despite his fiance's incarceration, and is deeply in love with Piper throughout the first season. He does suffer from insecurity and jealousy. This is shown when he discovers Piper's previous girlfriend Alex Vause is locked up with her.
As a journalist, it is clear that Larry desires recognition and fame, and he is shown to be very reliant on his parents for nearly everything, including money and advice. This coddling results in a high degree of gullibility in Larry, allowing him to live his life without Piper. Eventually, the writer manages to gain a bit of courage and confidence from his first big break: a story written about his own experience of having a criminal for a fiance. This does not distract him from the fact that "she's in there" and "he's out here" though, and provides a clear picture of the guilt and heartache he feels without her.
Surprisingly enough, Larry was committed to Piper to the extent of putting a ring on her finger and asking her hand in marriage. Yet, as revealed in a flashback, he was unsure of having a child with Piper, especially when she was about to be sent to prison. Thus, Larry may or may not be mature enough to handle a family.
- Ex-fiancé of: Piper Chapman
"Or I look single, 34 and single, which must mean there's something wrong with me. Like, I keep large reptiles in tanks, or I have a very special relationship with my mother."
"Well, I'm just gonna go jerk off then. For the 500th time today."