Tessa Robinson Character Profile

Tessa Robinson

34 years old, August 2nd

Interests - At this point in her life, Tessa's main hobby is drinking too much wine. She's 'focusing on her career right now' and that entails managing her store and trying to make it more profitable. She reads books on running a business, watches lectures on the topic, and does other things of that nature. Rather, that's her excuse. At most she watches the news and gets mad about things which doesn't really help her keep a positive outlook. Also plays the stock market which is another source of stress.

Humorously, Tessa enjoys watching romantic movies and TV shows. She claims it's purely ironic and that she does so merely to scoff at them, denying the fact that she clearly does it because she wishes something similar would happen to her.

Personality - Tessa used to be a very kind and friendly woman who was very outgoing but her personal struggles and the experiences she's gone through have rendered her something of a worn out husk at the start of the story. She's tired, annoyed, and it's everyone's problem. She has a general disregard for men because of her divorces and she tends to look down on most of them including Oliver. It's a personal irritation, she's not all radical feminist about it and it's more of a sarcastic thing she mentions often enough.

Appearance - Tessa has brunette hair that she usually wears in a bun. When undone, it reaches her shoulder blades. She is a curvy woman with a milfy body type. E-cup breasts, wide hips, and a very big ass. She is not thin and is a little chubby. Has a triangle of pubic hair. Her eyes are sharp and disinterested, irises being a cold gray color. She wears a pair of low hanging glasses that add a mature charm to her pretty face.

When working her store, Tessa wears a white polo, black dress pants, a green apron emblazoned with her store's logo on it, and a pair of brown one-inch pumps. For casual clothes she wears jeans, longsleeved shirts, and jackets more often than not. She has a modern woman aesthetic to her and cuts a sharp figure wherever she goes.

Family - Tessa's parents died in an accident when she was 24 and aside from some extended family she's primarily alone in life. Before that, her mom was a nurse and her father was the manager of large supermarket.

She has three ex-husbands, details below since they are relevant to her overall story and not just background lore. I'm not going to name them in this document, though. I don't know how big of a part of the story I want them to be and would probably rather leave it just down to offhanded comments here and there. Robinson is her maiden name, she had it changed back after her second marriage ended.

---

Tessa had a standard childhood with nothing really remarkable about it aside from it being privileged. She was very bright, had good grades, was always pretty and popular, and went to a good school. Her father being the manager of a store made her interested in business from a young age and it was her intention to go to business school to open up a store with him one day.

This plan got derailed when Tessa met her first husband, who was a Silicon Valley CEO-type who gave a speech at her high school way back when. Afterwards, the students got to have a meet and greet and ask him questions. Tessa really respected this guy at the time, but he was interested in something else from her. He slipped her his number and the instructions to text him under the implication that he'd mentor her.

Tessa was only sixteen as she was groomed by this wannabe tech magnate into an illicit relationship. He was a really unhinged guy and actually married her when she turned eighteen, much to her family's disapproval. She eloped to be with him and stopped communicating with her family for several years.

The upside to her relationship, if you could call it that, was that he put her through a fancy business college. Everything else became unbearable pretty fast because like all the others of his kind he is a crazy, unhinged person with more money than sense. She has a lot of weird stories about him that she can't legally share because of an NDA. The only ever had actual sex a handful of times, most of their relationship was weird kink stuff she tries to block out. There was a lot of emotional abuse and constant cheating on his part that she was forced to just put up with because of power imbalance in their relationship.

As her college graduation grew near, she reconnected with her parents and was able to get a divorce with their help. It wasn't a smooth process but it got done. He had a prenup so she didn't get half of his wealth but because of everything she could say to ruin his career and all the proof she had of him grooming her she did get a pretty big chunk of hush money that she used to open up her grocery store, Payless Foods.

She moved back in with her parents and shared ownership of the store with her father, the two of them reconnecting and bonding over its construction and management. Tessa was still young and although she had a degree she trusted him to manage the store as she worked alongside him to learn the ropes. It went well, but an accident happened two years after her divorce when she was 24.

Both of her parents died in a car crash, leaving Tessa devastated and now the full owner of her store. As many others have before her, she sought ways to deal with the pain and quickly gravitated towards drinking alone at bars- the reasoning for that being so at least she wasn't sitting at home crying about it alone.

A couple of months after the funeral, she ran into an old acquaintance while out one night. It was a guy from high school that she used to have a crush on before she met her first husband. They hit it off and started dating, but because Tessa was grieving, she was more vulnerable and didn't see any of the red flags. In a very stupid move, she agreed to marry him after only three months together. He was truthfully taking advantage of her depression to move things along so fast, and turned out to be a controlling and abusive person. Having already gone through this song and dance before, Tessa gave it six months before calling it quits and shoving his ass out the door. The sex was, again, unremarkable and it didn't happen often because of how fast their relationship deteriorated.

Tessa entered another 'working on my career' phase after that which unintentionally ended when she was 27 and went to Vegas with some college friends of hers for a bachelorette party. In the most embarrassing moment of her life, Tessa got drunk and ended up marrying a gambling addict. She doesn't even remember that night, but the pictures her friends took still haunt her memory. The guy was a total weirdo but she got him to agree to make the divorce quick by giving him some money.

It's been seven years since that happened and Tessa has not dated anyone since and has no intention to. She is incredibly bitter about love and specifically men, scoffing at the idea of romance. Despite that, she's not heartless and cares for most of her employees. She's even knowledgeable about Mia's crush and occasionally goes out of her way to set up chances for her despite how much she tries warning Mia about men.

Deep down, she wants to be proven wrong and wants to be swept off her feet. Tessa would never admit to it, but pretty much all her college friends are in loving relationships and have children now whereas she's just been stewing in her misery for all this time. She's getting older and is painfully aware of it and knows her chances are drying up.

---

Even more so than Stacy, Tessa is an impenetrable fortress when it comes time for Oliver to pursue her romantically. She doesn't initially respond well to any of the usual methods he uses and rebuffs most advances. He has to contend with her massive negative affection towards him but after he clears that it will become a little more straightforward even if progress is still slower with her compared to other heroines, primarily because of her stubbornness.

At first, working hard is a good way to get her attention and she starts seeing the effort he's putting in. This will soften her up as she doesn't want him working himself to the bone despite how grateful she is and she'll start speaking from her own experiences about how bad it is for you to focus so hard on your job. As the currently planned oldest member of the cast and the one with the most experiences, when Tessa starts to soften up with him she'll often have wistful advice like this for Oliver.

The age gap is another barrier for her, as is the wrongness of dating her employee. When she starts to fall for him, it will have many 'this shouldn't be happening' factors to it that Tessa is quick to try and deny and write off. It should make for a pretty entertaining character to watch her struggle with these growing feelings as an older woman who is being treated like the heroine of a dating sim.

Her heart events will focus on breaking down some of her barriers and helping her move on from her past experiences. Ironically enough, Oliver is in a good position to help her as he has experiences with hating the other gender just like she does. She doesn't think he can relate to her issues and while he can't imagine the pain she's gone through because of her past, he can relate better than she thinks. As her heart events escalate, things become more embarrassing for her as she tries to fight back her feelings, going to more and more lengths to deny them and put distance between herself and Oliver.

She will have to accept that it's okay for her to be happy and that it might take an unconventional relationship for her to do so. She puts up a big front about how self actualization is important in life and how the only person you need is yourself, and Oliver will argue it great if someone can do that, but Tessa kind and she's just pretending. She's lonely and she has to accept that fact if she ever wants to do something about it.

Post joining the harem, Tessa will feel out of place amid all the younger girls. She doesn't take on the same exact team mom energy that Suzette did in Coye. She's more jaded than Suzette was, whereas Suzette solved her 'problem' and moved on without needing someone's help. She will struggle to fit in but do her best and will end up looking after the other girls, just in a more seemingly distant way. Tessa will probably soften up with them over time, too.