Full name Jessalyn, Jessa is Jeff's girlfriend and Damsel's best friend. Jessa and Jeff met in high school, where he was a year ahead of her, while Damsel and Jessa met in the art courses they're both attending. She was first introduced by Jeff in the A Day In The Life video, and by Damsel in the 7/9/2010 entry in her journal, with the words "I made a friend", but only later it's revealed they're the same person. She has also appeared in the 7/24/2010 Ustream with the crew, and in a video on CYSTW. During the Ustream Jeff showed the audience a hamsa necklace that he intended to give to her. A hamsa is a symbol, that in Jewish folklore is a sign of protection. Jeff confirmed in a ustream Jessa's NOT Jewish.
Jessa disappeared between the 8th and the 15th of August 2010. In an attempt to find out the truth about what happened to her, Jeff "drove south", towards his old burnt out elementary school, finding out about Dr. James Corenthal. Vin and Evan started searching for Jeff via the #wheresjeff tag on twitter. Why Jeff chose south as the appropriate direction in which to find her is unclear.In the video "Congratulations, Magus!" Jeff can be heard saying that "We used to sit out here and talk all the time before she died." It is assumed that he is referring to he and Jessa. Towards the end of that video a shadowy silhouette can be seen. Jeff screams "Jessa!" and runs towards the figure. The EverymanHYBRID crew has stated that they do not remember filming that footage, and do not know how it became a part of the package that they sent to Magus.
In the video "Centralia" Jeff finds the hamsa that he had given Jessa buried in the dirt. He mentioned in the Angora Chat that he buried it for Trial 1 Part 2 of The Seven Trials of HABIT "near an old viaduct where [they] went to a picnic one time". It should be noted that Jessie is now wearing a hamsa necklace and before she disappeared Damsel hung these around her house for "protection".
At the end of "Centralia" Jeff decided to contact Damsel and enlist her help in looking for Jessa. This was one of the factors that led to the guys rescue of Damsel from the hospital where she had been being held.
A few weeks after Damsel's rescue Vince and Evan had Damsel's phone and intended to prank her by changing her voicemail. Instead they accidentally uncovered a saved voicemail from Jessa to Damsel that seems to be Jessa's last words:
- Voicemail Recording of Jessa's Voice: "[Static] Steph, Steph, that thing you were talking about [Static] I saw it, Steph I saw wh... he's real he's right here. You're right you're so right what the hell does he want? I think he's following me [screaming in the background] Steph, please please pick up [high pitched maniacal laughter] Oh god Oh g... [Jessa's voice distorts as the laughter continues. Then several bursts of static.]"
Jeff said in the description of the video where this was revealed that he simply regarded the message as "closure."
Jessa's final fate is still uncertain. However, in a tweet referring to the death of Sparky in the video One step forward, two steps back, HABIT heavily intimated that Jessa is also dead, saying, "IT APPEARS THAT BOTH OF THE BROTHERS KNOW A DEAD BITCH."
The description of "Twenty-four months" lists all the people who have been lost since this started and includes Jessa, heavily indicating that she is dead, or that at least the boys believe her to be. In the video "Lexi" HABIT confirms Jessa's death and says that she had been targeted because she was on the "outside," not on the "inside" like Vinny and the boys.
- Jeff killed Jessa under the Slenderman’s influence.
- Jessa is still alive but is being held by Slenderman.
- She was taken by Slenderman and killed. The bags found in Joke's Over are Jessa's body.
- Jessa became a Slender-puppet.
- Damsel murdered her under Slenderman's influence.
- HABIT and The Rake killed or captured her.
- Her voice can be heard in the Does anyone elses dog do this? video with The Rake's.