During the shoot of the music video for "First" (2005), Lohan revealed in an interview with MTV that she was preparing her sophomore studio album. "When you get into the studio, everything just comes out," she said. "All your creative juices are there. I don't [want to] leave. I'll still be in there until all hours, and it's nice to be able to do that." Lohan began writing lyrics for her album in June 2005, after her last single from her previous album had been released. "I've been writing a lot, almost every night," she said. "There's been a lot going on [in my life lately], and I think people can find that escape in hobbies that they do. I don't do yoga or anything, but some people use that. Everyone has their own thing, and I use writing." Initially titled There's Only One Angel In Heaven, the pop rock album features a darker theme when compared to Lohan's previous album, Speak (2004).
"Confessions of a Broken Heart (Daughter to Father)", the first track of the album, was mainly written by Lohan as a letter to her father, Michael Lohan, who was incarcerated in June 2005 after surviving a car crash for which he was charged with driving under the influence of alcohol. Additional writing and song production was done by Greg Wells and Kara DioGuardi, who revealed, "If you solo the vocals you'll hear race cars, because we brought the studio to [Lindsay's] trailer on Herbie: Fully Loaded. I'm not kidding! She had no time to do the record, so she would be on her lunch break, and I'd be like, 'Throw that thing down your throat and get over here, 'cause we got to finish these vocals!' So I sat for 14 hours on the set and would grab her for, like, 10 minutes at a time. The poor girl. That's the reality of young Hollywood. When they're hot, they're worked to death. It was 18/20-hour days. ... And I swear: 'Vroom! Vroom!' You can hear it in the back." "My Innocence" is also about the singer's father. Lohan also covered "I Want You to Want Me" by Cheap Trick and "Edge of Seventeen" by Stevie Nicks for the album.
A Little More Personal (Raw) received mixed reviews from critics. The album holds a score of 50 out of 100 based on 9 critical reviews, according to the music review aggregator Metacritic.Stephen Thomas Erlewine of Allmusic gave the album three stars out of five, saying, "Lindsay Lohan clearly spells out her ambition in the title to her second album, A Little More Personal (Raw) -- she's going to shed the glitzy trappings of her debut, Speak, and dig down deep in her heart, letting feelings flood onto the page". Erlwine also stated that the album "is far from being totally successful, it is an intriguing mash-up of heart and commerce. And it does suggest one thing that Speak never did: Lindsay Lohan may have an artistic vision as a recording artist, which is indeed a huge step forward".Entertainment Weekly 's Leah Greenblatt said, "like so many pop records today, Personal has more than its share of filler, and like all teenagers, Lohan contradicts herself. [...] Perhaps Personal 's vulnerability is calculated, and its rawness a misnomer, or maybe she's really opening up. We'll probably never know. Lindsay may no longer be on the edge of 17, but being 19, troubled, and ridiculously famous can cut pretty deep, so props to her for letting us see her bleed — just a little".
Brian Hiatt of Rolling Stone said Lohan "makes a fatal mistake on her second album: She tries to, like, express herself", while a Los Angeles Times critic also gave the album a negative review, claiming that, "for most of the album, [Lohan] sounds like any other self-absorbed teen, yearning to be Alanis, Gwen and even Stevie Nicks." Whitney Strub of PopMatters stated, "what can one expect from an album that promises to get more personal but includes lyrics declaring, “no one knows how I feel inside/And I’m keeping it that way” (from “Fastlane”)?", and commenting that "with A Little More Personal, Lindsay Lohan reminds us that, despite such blossoms, pop still has the potential to climb the charts while combining blandness, banality and vapidity". Sal Cinquemani of Slant Magazine considered A Little More Personal (Raw) "more consistent than its predecessor, and it's not a bad listen by any means, but for all the so-called weighty subject matter, there's not much meat on these bones".
"A Little More Personal (Raw)" debuted at number twenty on the Billboard 200 on the week of December 24, 2005, staying on the chart for seven weeks. The album debuted on the same week at the same position on Billboard Digital Albums, dropping the chart on the following week.A Little More Personal (Raw) was certified Gold in Taiwan, and Gold in the United States by the Recording Industry Association of America (RIAA), for selling over 500,000 copies of the album.
Following the album's release, it was reported that A Little More Personal (Raw) was certified Gold in Taiwan, and that Lohan was going on tour with the album in the country. "I just found this out today - my album went gold there. It was a great feeling because it was very unexpected", the singer revealed. "I would love to (tour Taiwan). I haven't toured at all at this point, but I would really love to do that. It's a great feeling to know that people in other places and other countries are aware of my music and what I do". The tour, however, didn't happen for unknown reasons. Lohan promoted the album in a few television appearances, including at MTV's Total Request Live on the day of the album's release, and at The Ellen DeGeneres Show on December 14, 2005. The singer performed "Confessions of a Broken Heart" and her cover of "Edge of Seventeen" in the 2005 American Music Awards.
"Confessions of a Broken Heart (Daughter to Father)" was previewed before the album's release at AOL Music's First Listen on September 30, 2005,. It was made available for purchase as a digital download and was sent to U.S. radio in October 2005. A music video for the song, directed by Lohan herself, references her father Michael's drunkenness and alleged domestic abuse, and was released on October 25, 2005. As a response to the music video, Michael Lohan wrote a letter to the New York Daily News, saying, "while I always considered and expressed how truly blessed Lindsay, as well as my other children are, I never realized how blessed I am to have a daughter as amazing as Lindsay. Hold onto my shirt honey, soon enough you'll be able to hold on to me!" "Confessions of a Broken Heart (Daughter to Father)" achieved moderate success, reaching number seven in Australia on the week of its debut on chart. The song spent thirteen weeks on the chart, peaking at number forty-five on the last. In Austria, the song reached number seventy-four on the week of March 24, 2006, dropping the chart in the following. In the United States, the song peaked at number fourteen on Hot Digital Songs on the week of December 3, 2005, while reaching number fifty-seven on Billboard Hot 100 on the week of December 24, 2005. The song was Lohan's first and only entry on the official Hot 100.