Basically Jake was Emily's first serious boyfriend I think (they had joint youtubes together and honestly seemed like goals, he really spoilt her and seemed to put her on a pedestal), Im pretty sure they got together when she was about 17 (correct me if im wrong) They even lived together which is very unusual for that age. They broke up after about 3 years in spring of 2017 when she was about to turn 20 basically this was also around the time when she started getting lip fillers and changing her appearance dramatically. There was some rumors that they were on again off again as she went to disney world with him in late spring. Then in the end of 2017 she started dating Charlie, a guy from her school, I believe it was a bit before Christmas time because that was the year she was hanging with Libby a bunch during Christmas and there was mention of there being a secret guy or something, but she only had him on her channel for a few months (ex. they went to disney world and a cruise in the end of march) before revealing in the early summer of 2018, when she was 21, that he had cheated on her and they split up, they only dated for about 6 months i believe. She then started dating James basically immediately after and here we are 2.5 years into her dating James and it seems terrible. Hope that gives you somewhat of a timeline