|May and Jason|
|Status||Broken up (enemies)|
May and Jason met in 1813 when she found Jason dying due to a shotwound on the battlefield. She decided to turn him and they fell in love quickly.
|“||You were the first guy I invisioned eternity with||”|
— May to Jason when he awakes as a vampire
The affair got serious to the point where May was ready to assign him as her mate. To test Jason's obedience to the rules, she plans a trip to his hometown area of Boston. When he passes the test by not contacting his family, she is certain of her choice. She tells to him that she plans on finding a way to have a child, something Jason had stated as his biggest regret about not living a human life longer.
However Jason soon learns this was all just a distraction from the fact that May had fallen for Jason's human brother Jared. May holds off on declaring Jason as her mate, and Jason starts to notice she gets more distant. He gets told she is just busy recruiting. What Jason does not know, is that Jared is one of May's recruits, and the two begin an affair behind Jason's back, that goes on for several months
When May packs her stuff from the compound, Jason confronts her about her distance. She then bluntly tells him she was having an affair (not telling him with who). Jason runs out of the house, and goes on a rampage. He briefly returns to the compound to get his things, which is when May tries to get him to forget about the betrayal and go with her. Jason tells her he will leave and he never wishes to see her ever again. He leaves behind his position of Commander amongst the Millers. At this point, Jason does not yet know May is pregnant with his brother's child, and May is hopeful the child is Jason's, not Jared's.
Many years later, Jason comes to befriend that child, Alyssa, who also abandons her mother. When Jason finds out she is a member of the Millers he grows nostalgic to the time he spend with them and May, but ultimately both Alyssa and Jason decide to leave the chapter behind them. Alyssa does not mention May is her mother, and not just her sire.
When Jason finds out about this he digs deeper into Alyssa's time at the Millers, and he finds out she was born in 1813, the year he left the Millers. He then performs a DNA-test, where he concludes they are related but she is not his daughter, leaving him to conclude she is his niece. One night in Vegas he tells her what he found out, and the two of them agree that this doesn't change anything about their friendship, which has been doing on for over 250 years.
Alyssa tells her mom she found out who her father is, but she doesn't tell May who she learned it from. Regardless, May suspects Jason knows and plots her revenge against him and his new family, attempting to wipe them out.
Jason and May meet again almost two hundred years later. May, who heard about Jason having a child with a powerfull Silverstone witch, is jealous and plans on destroying Jason's life.
After two previous attacks May gets help of a powerfull wizard of the Hainasoni and mind-compells Jason. Jason , under compulsion , thinks he is in love with May again. When May wants to take him to her bedroom , to sleep with him and kill him after it , Jared is the one coming to Jason's rescue. Right after this , May kidnaps the children with help of an insider (Tyler Cole). However , when Payton shows up and trades her life for her children's , May can't refuse the thing she wanted the most , and that is to get rid of Payton. May drinks Payton's blood , unknowing her blood is poison , and dies.
A few months later , May shows up again in Jason's head as a voice , his dreams and eventually as a ghost , begging him to get her to the other side. Jason tries to block her out but has no other option than to keep the connection when Alyssa reveals she needs her mother to confirm who her biological father is. Alyssa happened to be and impotant person in both May and Jason's lives. She is May's daughter and Jason's best friend. However , in one of the battles with May , Jason gets doubts (caused by Thomas) about who Alyssa's father is. May plays in on this by saying he is actual the biological father , saying she was already pregnant before Jared arrived. However , later May will reveal in Purgatory that Jared is in fact the real father after being promised to go to the other side. Jason and Alyssa both agree to honor the promise and the portal is opened , only to be shut down by Payton again , stating May should rot in hell.
- Love the way you lie