The season starts with Larry and Pete Harper, standing over a "guilt" pig-roasting box and they prepare Larry's fiancée's, Piper Chapman, last meal before heading off to prison. After the meal Piper and Larry are in bed and they deicide that they "gotta do it," once more. Before hand Piper needs to pee, as she gets up to go to the bathroom Larry says she looks beautiful. On her return she says he looks beautiful too and they have sex.
The next day Larry drives Piper out to the Litchfield Corrections Facility for her self surrender. The two sit in the car for a moment and she hands her engagement ring back, saying she can't take it with her. Larry tries to but the ring in his pocket, which upsets Piper, but the two reconcile quickly. As they wait for the CO's to take Piper back there's a flashback of Larry and Piper sitting in her parent's hosue telling her family about her crazy post-college adventures and that she was going to jail. Piper's father questions Larry on his knowledge and he tells him he didn't know before hand.
After Piper is taken back there's another flashback of Piper and Larry at the beach. They have a brief conversation about what she plans on doing in prison when Larry proposes. He gives her his Great-aunt Marcia's ring. After she says yes Larry revels that he filmed the whole proposal.
Later in the first episode, Larry and Piper are sat in their bedroom. Larry has just discovered Pipers past. Larry is clearly upset, but confronts Piper when she begins to cry. She tells him to break-up with her. He says he's not going to and that they will deal with it. Larry calls his dad, Howard Bloom, who is a lawyer, to represent Piper.
When she's able to, Piper calls Larry on her first day and tells him all about it. He tries to calm her and and tells her that she is strong and that she can do it. He reminds her that it's all temporary and that she loves adventure. He agrees to see her the coming Friday.
When Larry goes to visit it seems like the CO's are messing with him. He goes up to the counter and when he tells the officer behind the desk, Wanda Bell, that he should be on the list she says he isn't on the list, but then notices it's the list from the previous week. She's in no hurry to get the list and tells Larry to have a seat while she calls to get the list.
One day, Piper called Larry and asked him if Alex Vause, Piper's ex-girlfriend, had named her and was the reason for her arrest. His father,Howard Bloom, who is also Chapman's lawyer, searched his files and found out that Vause did, in fact, name Piper as a suspect. Larry was insisting on telling his fiancé, but after seeing her on the brink of going crazy, he decided to keep this knowledge a secret.Knowing that his wife's departure to jail would come soon, he spent his last few days with her having some really hot and heavy, straight sex. When the time came, he drove Chapman to the prison and, before getting out of the car, accepted her engagement ring and placed it in his wallet for safe-keeping. They waited for a few hours before they finally took Piper in, and promised to have her money ready in order for her to buy whatever she needed in prison. He called Piper and saw her as much as he could, although conjugal visits were prohibited.
With Piper gone, Larry took it upon himself to live his life the way he wanted. He began writing more and spent a lot of time masturbating, as he still felt faithful to Chapman. She would often confide in Larry about the drama going on in the prison, and he soon wrote an article about it titled, "One Sentence, Two Prisoners." Sam Healy, who became jealous of Chapman's new-found fame, called Larry and told him that Piper and Vause had had a lesbian affair. This left him heartbroken and confused about his feelings toward Piper. He later went on a radio talk show and spoke about the inmates, which caused more drama within the prison.
After Bloom and Chapman spoke on the phone, he revealed that Alex had named her as a suspect, and mutually decided to end their engagement.
After breaking up with Chapman, Larry became a lost dog looking for new love. Although reluctant at first, he found relief in Piper's best and long-time friend, Polly Harper. He had gone to see her and her baby, and found out that Pete Harper, Polly's husband, had gone on a month-long trip to the north. He stayed with Polly numerous times and were even mistaken by an older woman to be married themselves. Soon after, they ended up having sex in Bloom and Chapman's home. When Chapman was released for two days through furlough, she attempted to have sex with Larry, but instead, he ended up confiding about having sex with someone she knew. Later on, Polly and Larry decided to stay together and told Pete. Piper soon discovered that Polly was the one whom Larry was seeing. The two later visited her in prison to ask for her blessing.
Larry initially comes across as a very loving and devoted partner for Piper, proposing marriage to her before her sentence and promising to wait for her. As the series progresses, Larry's egotistically selfish character is revealed repeatedly as he does things without considering the backlash he causes; only considering what he can gain out of it. He also is seen to have a vengeful attitude at times.
Larry has close cropped dark brown hair, brown eyes, and pale skin. Some question his sexuality due to what he wears.
- "Why wouldn't I want a felonious former lesbian WASP-Shiksa about to go to prison to marry me?"
- — Larry Bloom ("I Wasn't Ready")
- "This is all just a big adventure with liver and Yoga Jones, and... and... and racism."
- — Larry Bloom ("I Wasn't Ready")
- "If only my nipples smelled like marzipan."
- — Larry Bloom
- "Freedom of press shouldn't only be a privilege of the free, right?"
- — Larry Bloom to Piper ("You Also Have a Pizza")
- His great-aunt Marcia had thyoid cancer and a series of schnauzers all named "Schnapps", as mentioned in "I Wasn't Ready".
- In Larry's youth, there were some embarrassing events he calls "the webcam horror" and the "penis shaving incident", in reference to Jason Biggs' character Jim Levenstein's experiences in the movie American Pie, as mentioned in "I Wasn't Ready".
- He has an aunt named Joanie who has a boyfriends who seems to be an eco-freak frequently talking about "deceased cows on dairy farms, horrors of genetic engineering, overuse of antibiotics in cattle" on family reunions--and he takes his coffee black, as mentioned by Howard in "Thirsty Bird".