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Jeb Friedman knew the reporter Lois Lane since she was young[1] and claimed to be the first person to ever develop feelings for her.[2] He also acted an informant who provided Lois with information concerning Intergang. During these meetings, Jeb developed a fondness for Lois, even though she was already engaged to marry fellow reporter Clark Kent. Despite his oblivious intentions, Lois and Jeb became friends, although it made Clark more than a little jealous.

After Clark's death, Jeb tried to cheer her up and took her away to coffee and later dinner so she took care of herself. The two kissed and Lois regretted it since she did it out of grief and was lonely, but she wanted Clark even though she knew Jeb genuinely cared for her. She then decided to get away from Jeb and focus on preserving Superman's legacy[3], coming to know he was alive only a day later. Jeb thought his chances were ruined now that Superman was back.

Jeb saw Lois and Clark again while organizing Babe Tanaka's metal concert, with the profit going to the underprivileged in the aftermath of M Clark argued that it wasn't right as Metropolis was a disaster zone. Jeb called him a coward for thinking that but Lois broke them up before things got out of hand. He was later attacked by mutants of Earth-31, who took Metropolis' destruction heralded its judgment day and didn't want him rebuilding the city. He was however rescued by the Batman of Earth-31. After the concert, he told Lois that he was puzzled by what she saw in Kent, joking about giving him a try since she can't decide between Clark and Superman. Lois stated that she'll stick with what's she has and kissed him goodbye. Jeb joked that she should tell Kent that he saw her first and joked that she should marry him quick or he'll come back for her. He then went to Paris where he bought a scarf for her as a gift.[2][4]

After a series of troubling incidents, Lois ended her engagement with Clark. Lois contacted Jeb about the mob's connection with the fisherman union and Clark became jealous when he found he was going to buy her lunch. After joking about Lois using him to make Clark jealous, Jeb cautioned her for contacting him about the mob and stated that she was trying to take her mind off her breakup by doing this dangeorus job. Lois confronted him about the mob but he expressed ignorance. He was later confronted by them over Lois snooping around and told to make sure she didn't expose them. Lois after witnessing this, forced him to help her with her investigation involving the mob activity. He agreed but told her not to expose them now.[4][5]

Lois was troubled about having to hide the truth about the mob who had even bribed the mayor or making Jeb a target. She hatched a plan with the police commissioner to get abducted and be rescued by the cops in order to expose them herself. Jeb left a folder for her detailing the mob's contacts and a message for her regarding it, in which he told her to get Superman and Clark's help while also telling her that he loved her. The mob had however used her to get to Jeb, who was unaware of Lois' plan and he died trying to save her. Superman, who had come to know about her investigation through Jeb's message, saved her but was unable to recover his corpse alone. She greatly regretted her death and told Clark that she knew Jeb always loved her. He then asked Lori Lemaris to help and was able to retrieve it.[4][5]

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