Tattoos Greg has gotten and tattoos others have gotten for him.
**During the events in this article, Kai went by the nickname "Lainey" and did not yet identify as a trans man. The writing in this article will reflect Kai's current name and pronouns, but images, quotes, and videos will not.
During the early years of his Speaks channel, Greg made videos about how he believed tattoos and piercings were body mutilation. He was avidly against them. All of these videos were removed from his channel.
After getting his "Remember Love" tattoo in 2011, many confused viewers questioned why he got them if he believed tattoos were mutilation. Greg responded with a video explaining his girlfriend Shiloh changed his views on tattoos. This video has been removed as well.
In 2020, after getting 6 tattoos, Greg concluded that tattoos are cool at first, but over time he stops caring about them. Unless it was incredibly symbolic, like for a dead grandma, it just becomes a doodle. ($ource)
Remember Love$ource) Shortly after, Shiloh got "Gregory" tattooed on the back of her neck.
Adrienne, who dated Greg in-between Shiloh, claimed Greg told her he and Shiloh planned to get each other's names tattooed after a short breakup. According to Adrienne, Greg was originally supposed to get "Shiloh" on his wrist, but got "Remember Love" instead the last minute. (Source)
After his break-up with Shiloh, Greg says he does not regret his Remember Love tattoos because it is still a positive message. (Source)
In 2019, Greg revealed he got the "Remember Love" tattoo to remind himself to not look at Hentai. He explains he told Shiloh he had been watching hentai and she broke up with him and left the apartment they lived in. He won her back by telling her he would get the tattoo. He says she got the "Gregory" tattoo not long after he got his tattoo. He mentions he could have gotten her name on his wrists, "but that would have been a problem." ($ource)
He later said he specifically got the tattoos on his wrist so he would see them when he would try to jerk off. ($ource)
For years, when asked about this tattoo, Greg would only say it's a significant date. (Source) Kai says 27 is his lucky number.
In 2019, Greg spoke more about "27". He says the number 27 is a number that contently pops up in he and Kai's life. He says the plane he went to visit Kai on was "2727", the hotel they stayed in was number 27. He says 2 and 7 were his favorite alternating numbers his whole life. ($ource)
11-14$ource) Greg's 4 is blue and Kai's is pink. The 14 is for the day they were married, November 14, 2012.
Like the 27 tattoo, when asked about this tattoo, Greg would just say it's a significant date. (Source)
In 2019 Greg revealed this tattoo is actually a "11-14". He says this tattoo is for the day he almost ended his life, November 14, 2007. He says he unintentionally got legally married on the same day. He says he got the tattoo for his relationship, but jokes if they break up he will still have the other meaning. ($ource)
Do Not Engage$ource)
Three days later, Greg revealed his Do Not Engage arm tattoo in the video "REVEALING MY NEW TATTOO! (+ Weight Update & Pull Ups)". In the video, he explains the two wings on the sides are dove wings and they represent peace. In the middle is an olive branch to also represent peace. The first "O" represents peace and the second represents balance between light and dark. He explains "Do not engage" is for reminding him to his commitment to the philosophy that when you engage with people, they are fixed in their ways so it's futile and a non-positive use of your time. ($ource)
Tattoos On Others
ShilohSource) Greg says he never asked her to get the tattoo. He says she surprised him with it and he was overwhelmed by it because he has never asked anyone to tattoo his own name onto their bodies. ($ource)
Greg later claimed Shiloh told him she went to a tattoo artist in Toranto for the "Gregory" tattoo. The artist told her they wouldn’t do it unless the name is of someone in her family. She told them it was her grandfather’s name. She came back and showed it to Greg and he felt nervous and panicky because he thinks it’s a bad idea to get someone’s name tattooed on your body. She seemed happy and it was too late so he played along. ($ource)
In 2019, after Shiloh was interviewed by Chris Hansen about her relationship with Greg, a GoFundMe was created to pay for a cover-up tattoo for her "Gregory" neck tattoo. Over $3,000 was raised. (Source) In December, Shiloh announced the tattoo was covered. She tweeted a photo and thanked supporters. (Source)
Greg accused Shiloh of using the tattoo cover-up to scam money from her fans. He claims he was told her tattoo was already covered up years ago. ($ource) He believes the cover-up tattoo she got only would have cost $50 and accuses her of keeping the rest of the money for herself. ($ource)
In 2018, Kai got a three flower tattoo designed by Greg. Each flower represented a member of their family, the biggest one representing Greg. Greg's flower is yellow for his birthstone. ($ource)
Also in 2018, Kai got a surprise tattoo for Greg on their 6th wedding anniversary that said "You are my strength" in Greg's handwriting. Kai filmed Greg's reaction to the tattoo for the video "SURPRISING MY HUSBAND WITH A TATTOO" on his Youtube channel. ($ource)
BillieBillie in November 2016, Greg told Billie she could stay and win back he and Kai's trust if she got a tattoo of a lily flower with the word "Lillie" under it. He explains, Lillie is his ship name for Kai (Lainey) and Billie. He says he showed her his "Remember Love" wrist tattoos and told her in the past he had done something similar. He says because she already had tattoos all over her body, it wouldn't be a big deal. ($ource) Billie did no get this tattoo, but began dating Greg and Kai again a month later.
After Greg broke up with Billie for the last time in early 2017, it was revealed he had asked her to pick one of many extreme actions to win back he and Kai's trust, one of them being getting a tramp stamp tattoo that says "I'm a liar". Greg justifies asking her to get this tattoo by saying if someone lied to you in a relationship, it would require them doing "something grand" to make it up to you and show how dedicated they are to you. (video deleted)