Even Aiko – the second-oldest – is eight years younger than her. Though this was really kind of inevitable as Jessie is the oldest of the human characters by a pretty long way.
Intergenerational Friendship: Both of her shown friends Beli and Lola are substantially younger than her (by 13 and 12 years respectively). Impossibly Low Neckline: Her 'Playful Bunny' outfit. She also genuinely seems to care for her daughter and wants to reconnect with her. Hooker with a Heart of Gold: Technically, she's a porn actress rather than a prostitute (the similarity comes from her gold digger attitude toward dating), but Jessie's also one of the most patient girls in the game when it comes to the player character, sometimes even consoling them after a failed date. It's clear that she mostly lives to have a good time and loves drinking and sex, but she doesn't do drugs or act obnoxious for self-gratification, and she does express a desire to reconnect with her daughter. The Hedonist: To a lesser extent than Audrey. Hard-Drinking Party Girl: Will accept drinks from the player any time of the day and has a high alcohol tolerance to boot. Though since Tiffany was born twenty years ago, it's possible abortion wasn't an option (or at least, not an accessible one). Good Girls Avoid Abortion: She had Tiffany, even though it would force her out of high-school and make her life extremely difficult. However, she was even younger when she got pregnant with her daughter, and has managed to play up the MILF stereotype to the hilt. Glamorous Single Mother: Like Kyanna, she is a single mother. Friends with Benefits: She has no interest in romance, but will gladly have sex with you if you both enjoy it. Although she's been a pretty irresponsible person for a long time, she's still a mother who values family and wishes she could be closer with her estranged daughter. Kyu certifies that despite being a porn star, Jessie is clean of any STDs. Very forward with her sexual intentions without any kind of shame, but you've still got to avoid bad dialogue choices or matching heartbreak tokens because she doesn't think being a jerk is sexy. She's fallen into deep depression after the end of her porn career and drinks to forget her mistakes. Drowning My Sorrows: Implied in HuniePop, but confirmed in HuniePop 2. Dark-Skinned Blond: Not that dark, but she's got a pretty deep tan. She's described as depressed and desperate for any kind of sexual attention, to the point where she'll do anything to feel young and desirable again. However, by the time of the second game, she's been forced to retire from that career, and was left feeling used and discarded as a result. In HuniePop, she was quite sad on the inside but outwardly good-natured and happy with her career as a porn star. Darker and Edgier: Her HuniePop 2 appearance seems to be going down this road. Cowgirl: One of her unlockable outfits is a sexy cowgirl costume. it's her body we see in the official trailers. While she's not the face of the franchise (that'd be Kyu), she does get the most focus in the marketing for the spinoff. Black Bra and Panties: Gains a set of these in HunieCam Studio. 
Taken even further in HuniePop 2: after losing her job as a porn star and falling into depression as a result, she'll do anything for sexual attention to make her feel young and desirable again.
Attention Whore: While she began in porn because she needed the money, at the end, she liked the attention and fame it got her and stuck with it. She also responds positively to the player insinuating that they have dark secrets they're keeping from her. All Girls Want Bad Boys: She likes men who are unapologetically sexually aggressive. Alcohol Hic: Lets out one occasionally when being given certain gifts. Tropes exhibited by this character include: PAGES WILL BE DELETED OTHERWISE IF THEY ARE MISSING BASIC MARKUP. 
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