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Luigi Mangione became an unexpected heartthrob after he was arrested in connection with the assassination of UnitedHealthcare CEO Brian Thompson. Instead of outrage over Thompson's killing, women swooned over accused Mangione who was painted by some as a vigilante as opposed to a murder suspect. But the man whose mugshot was deemed one of the 'hottest' of all time never once had a girlfriend despite being flirtatious and close to several women, it has emerged. Mangione, 27, was 'alienated' and often talked of loneliness, author and former journalist John H Richardson revealed in his new book Luigi: The Making and The Meaning. Richardson spoke with Mangione's friends and acquaintances, all of whom painted a picture of a nice, good looking guy who was looking for intimacy yet puzzlingly lived a perpetually single life. A female former University of Pennsylvania classmate who befriended Mangione while they were both staying in co-living housing in Hawaii shared how they would go on mile-long beach walks and engage in deep conversations but never shared a kiss. Another woman he met on the island revealed they went on getaways together which Mangione planned, although Richardson said there was no explicit mention of romance. However a journal entry penned in jail contained a tantalizing hint in at a possible change in his relationship status, according to the book. In May, ahead of his 27th birthday, Mangione wrote a gratitude list featuring 27 things that he was grateful for. The list started with his friends, family and 'for [REDACTED - my personal life is none of your business!]' Could the remark be just another snarky comment about his perpetual singleness or is it a hint that Mangione has possibly found love from behind bars? As a child, Mangione attended Catholic school until sixth grade when he transferred to Baltimore's elite Gilman School for boys. The so-called 'brainiac science geek' seemingly excelled at the preparatory academy. Teachers said he volunteered as a writing coach, praised his classmate's accomplishments and demonstrated 'humility, kindness and affability'. Mangione was 'always keeping everybody's energy up,' one high school friend told Richardson. But despite his apparent charisma, he never had a girlfriend with one friend speculating he 'might have been shy.' In college, he appeared to have a wide assortment of friends and was active in many campus clubs and activities, including being a member of the Phi Kappa Psi fraternity. During his junior year, Mangione's photograph was featured on a Facebook group titled Penn Crushes. 'Hot damn. Are you single? You make us engineers have hope!' one user commented, according to the book. Mangione simply replied: 'Despite my best efforts... yup still single.' After graduation, Mangione moved to Hawaii. He was actively on Tinder until 2022. His disappearance from the app seemingly corresponded with injuring himself in a surfing accident. The accused killer, in a letter to a fan, claimed he spent '1.5 years living with a broken spine' and could feel his spine slide around whenever he moved. 'He knew that dating and being physically intimate with his back condition wasn't possible,' his friend R J Martin, founder of the Surfbreak co-living community, explained. Although he never dated anyone officially, fellow Surfbreak resident and UPenn alum Jackie Wexler implied she was emotionally intimate with him. Wexler recalled how she and 'thoughtful and deeply companionate' Mangione would regularly take one-mile walks from their residence to Honolulu's small man-made Magic Island peninsula and watch the water together. The pair also co-founded a book club together. Wexler claims Mangione was a 'deep listener' and would often take a lead role in discussions. Tracey Le, who also met him in Hawaii, appears to be the closest Mangione ever got to having a girlfriend. Le claimed once in an Instagram post that he was the 'number one' amongst her favorite friends. She went to him with everything: identity crisis rants, relationship problems, career complaints and more. On the surface the man she praised for being 'caring, smart, mature, sweet and considerate' appeared to be nothing more than her best friend. But Le also how she 'always 100 percent depended on him to plan the trips' they took together and 'always 100 percent believed we would have the best time'. Heartwarming videos of the pair shared on social media show them sharing laughs, hugs and Le even leaning her head on his thigh. While living in Hawaii, Mangione appeared to be struggling with the concept of masculinity, as detailed in lengthy books reviews on his Goodreads account. In one thread he reshared a quote from self-help author Tim Urban criticizing singles events. The quote read in part, 'I'm yet to see one of these undignified dances that actually ends with the guy getting laid.' Other social media posts from that tome period saw Mangione repost content questioning 'what are men good for?' and others examining the harmfulness of masculinity. Mangione's loneliness did not subside once he left Hawaii another friend has revealed and his social media posts suggest that he was a fan of pornography. In January last year, the ex-data engineer defended adult content in a comment replying to a right-wing poster arguing on behalf of a pornography ban. 'Porn should be regulated no less than alcohol, cigarettes and travel,' he wrote. The posts, which were highlighted in Richardson's book, are unsurprising given previous reports that Mangione has starred in highly stylized sex tapes. There are 'at least 20 videos of him having sex' that he filmed and 'wanted to be watched', an insider told RadarOnline earlier this year. 'It wasn't just some grainy, late-night mistake. It was perfect lighting, everything,' the insider claimed. 'He wanted to be watched. He got off on it.' The person went on to say 'a lot of the girls are too afraid to come forward or tell anyone for fear they might get dragged into his case somehow.' Gurwinder Bhogal, a popular Substack writer and friend of Mangione's, allegedly spoke to the accused killer on May 5, 2024 - the day before his 26th birthday. During their video call, Mangione discussed the 'loneliness of modern life' and appeared 'alienated', Bhogal told Richardson. He claimed Mangione felt 'other people were on a different wavelength' and even urged Bhogal to start a 'social club for like-minded people'. Mangione was arrested last year over the fatal shooting of Thompson on December 4 as he arrived at a Manhattan hotel for his company's annual investor conference. The killing set off a multi-state search after the suspected shooter slipped away from the scene and rode a bike to Central Park, before taking a taxi to a bus depot that offers service to several nearby states. Five days later, a tip from a McDonald's restaurant about 233 miles away in Altoona, Pennsylvania, led police to arrest Mangione. He has been held without bail since then. Mangione has pleaded not guilty to state and federal charges, including murder, stalking and firearms offenses related to the killing. His lawyers last month asked a New York federal judge to dismiss some of the criminal charges, including the only count for which he could face the death penalty.
