Tessa and Ryan first met in the second episode The Barbecue. They dated shortly in the episode then separated. Ryan continues to crush on Tessa for the rest of season one and much of season two, though Tessa seemingly doesn't reciprocate the feelings. They start up dating again in season two after she helps him deal with the news of him being adopted. They later break up as Ryan is going off to college and Tessa is staying in Chatswin to complete her senior year. In season three Ryan comes home to visit with his new girlfriend, June, who is astonishingly similar to Tessa. The last episode of season three ends with Ryan and Tessa making out and taking off each others clothes in the middle of the street therefore rekindling their relationship.
There wasn't that much interaction between Ryan and Tessa in season one.
Ryan and Tessa first appear together in The Barbecue. Tessa and Ryan are in th basement of Sheila and Fred's house with Dalia and her friends. Dalia dares Ryan to kiss a lesbian and Ryan states he will not kiss his sister. Dalia explains she meant Tessa, so Ryan kisses Tessa after her protesting. The kiss lasts longer than expected, and Tessa keeps thinking about Ryan and her. The next morning, Tessa awakes to Ryan, stripped to the waist, washing his car across the street and obviously trying to attract her with his hot bod. Tessa is flattered and stares, without realizing Lisa sees her from her window.
At school, Lisa tells Tessa what she saw angrily and walks off. Tessa is worried about the fact that she is attracted to Ryan, who she thinks is stupid. She tries to cure herself by kissing a nerd named Evan, but this does not work and she walks away with Evan looking shocked. Later, Ryan asks Tessa to join him underneath the benches at their track. She agrees, and later the two are found kissing underneath the bleachers. Tessa tries grilling Ryan to see if there is anything up his sleeve, but he is the same as usual, i.e. as thick as two short planks.
Later at George's barbecue, Tessa and Ryan are found making out in the laundry room. After being motivated by Lisa, Tessa tells Ryan that they can't be together and compares it to "eating chips and regretting it". Ryan compares her to "peanut brittle", and that he is "breaking her into tiny pieces", therefore breaking up with her, which is what Tessa just did to him. He walks out in a huff, with Tessa wondering if Ryan isn't as stupid as he looks.
Sex and the Suburbs
After staying the night at Lisa's house, the family and Tessa go for breakfast at the country club. During breakfast Ryan states that he knows Tessa is dating Scott and that he approves because he has nice hair. Lisa tries to make him shut up but he carries on saying that it doesn't hurt him to see them together, but in the end blurts out that he wants her back and Tessa uses an excuse that she's getting muffins to quickly leave.
Down TimeWhen Lisa gets a text from Tessa asking what they're doing during the weekend, they decide that they should try and 'hook her up' with someone. This seems to gain Ryan's interest. On Friday night, when Tessa has nothing to do because she doesn't want to be the third wheel to Lisa and Malik, she tells herself that she is happy to have time to herself.
She starts eating butter, watching Extreme Makeover: Home Edition, playing with dolls and eating more butter, when Ryan knocks on her door and surprises her. Tessa asks him if he was watching her, to which he admits. He then says that she 'fell off' and that she's eating too much butter, He says that when he heard her sister talking about hooking her up with someone; he thought that because she'd made out with him, she could get anyone. But after watching her from the bushes, he's not so sure.
Tessa tells him that she's not herself and she admits that maybe she is leaning on butter more than usual but says that she is a recovering tricycle trying to get by on one wheel. Ryan says that he's been there and asks if she wants to get something to eat because her pajamas (with print of various foodstuffs) are making him hungry.
Later, Tessa and Ryan enter a fondue restaurant and Tessa sees Malik and Lisa. Tessa then tries to leave and says that they should go somehwere else. Ryan wants to stay becuase he wants a bowl of wet, hot cheese and the forks are long. Tessa agrees to stay but says that they should get in there before Lisa or Malik sees them.
When Lisa is feeding Malik, she stabs him in the lip with her fork becuase she has seen Ryan and Tessa together. She says that her heart is breaking because Tessa has 'bottomed out' and quickly makes her way over to them. She claims that she can't even imagine how lost Tessa must feel to resort to Ryan.Tessa tells her that she's fine, Lisa should stop pitying her and that Lisa had her pitying herself. Ryan agrees with this telling Lisa that he caught her eating butter. Tessa tells Lisa that she doesn't have to feel guilty about doing things without her.
Lisa says that Ryan should go home, but Tessa interrupts her saying that they were having a nice time. Both Ryan and Lisa ask, "Really?!" and Tessa says yes. Lisa looks slightly disgusted by this but Ryan looks happy.
Later Ryan and Tessa are walking to her house and Tessa says that it was fun and thanks him for getting her out of the house. Ryan tells Tessa that his mom says that when you want to say thank you, you should send a thank-you card but that he really wants to touch her boob instead. Tessa agrees, but says he only has three seconds and pulls back her sweater. When he pulls back he asks her what her address is and Tessa tells him he doesn't have to send her a thank-you card and leaves.
Season two was noted for Tessa and Ryan trying to make their relationship work.
In this episode, Tessa is at Noah Werner's place babysitting Opus. Ryan jumps onto Lisa's bed, after she gives him her room. Ryan then asks Lisa, if he could have her sweater, and then a snake, and then if he could have Tessa because she's his moose. Lisa corrects him, by saying muse. She's his jam, and Tessa is what Ryan wants.
The hillside electrical strangler comes looking for Mr. Werner, and Tessa is afraid to let the man inside the house, so she locks herself, and Opus in the bathroom, and calls Lisa to come keep her company. Lisa then suggests that Ryan go over to the Werner's place to keep Tessa company.
Ryan runs all the way from his house to the Werner's, and when he gets there, Tessa tells him that she could kiss him for being there with her. He puts his hand on her face, to stop her from kissing him, and then he tells her he thinks that he is dying, because Lisa has been so nice to him recently.
Ryan then starts ranting about how he thinks he's dying, and how they should call his disease Ryan's disease, and then maybe start a song called Ryan's song. Ryan then starts talking about how everyone is going to die eventually, and Opus starts crying. Ryan shushs baby Opus by whispering "Shut up, shut up, shut up." Tessa then tells Ryan nice work on getting Opus to stop crying. Ryan then asks Tessa if it's too late for the kiss that she was trying to give him earlier.
Tessa then goes to kiss Ryan on the cheek, but he bends down, and kisses her on the mouth. Ryan then tells Tessa that she "forgot to open her mouth, and put her tongue on his tongue, and move it around and stuff". Tessa then tells him that she didn't forget.
Ryan then asks her if she's attracted to him because he's holding a baby, and Tessa tells him that she's only attracted to him because he's holding a baby.
Ryan tells his father that he wants the wishbone from the turkey because he has a wish he wants to make, and that wish is to make love to their neighbor. Fred mistakes the neighbor for someone else.
Ryan finally finds out that he is adopted, and runs away from the Shay family. At the end of this episode, Lisa asks Tessa to go talk to Ryan, because he's crazy about her. He always has been. Lisa then tells Tessa to tell Ryan that she loves him too.
Tessa finds Ryan, and she tells him that she can relate to him. Ryan then pulls out a business card that he made with Malik's printer that has his new name "Eugene Goldfarb" on it. Tessa then tells Ryan that he isn't Eugene and that he's Ryan Shay, he lives across the street from her, and that he has a huge crush on her.
Tessa then tells Ryan that she might have a crush on him too. She then kisses him, after their kiss, he starts shouting triumphantly, "She used tongue! She used tongue!", while Tessa is laughing. He then tells her that that was the only thing on his christmas list that year.
Tessa suggests that the two of them go home, but Ryan then proceeds to run away.
Junior Secretary's Day
Lisa gives Ryan Tessa's homework since she just had her wisdom teeth pulled out, and is in no condition to go to school. Ryan goes to Tessa's house to give her the homework, and while he's there, he ties a sock around her head, that's filled with ice, to help with the swelling and the pain of her teeth getting pulled out.
Ryan remarks that Tessa looks like a bunny. He then brings up the kiss that they had in the episode "Krampus" and Tessa says that they've tried it before, and they are total opposites. But then agrees with him that opposites do attract.
Ryan tells Tessa that he's super attracted to her right then, even though her face is puffy and her gums are bloody, and her lips are dry, and asks if it means something. Tessa then tells Ryan that it hurts to smile, and he says, he makes her smile, even when it hurts to smile. Her smile convinces herself that even though there's a huge difference between them, she might be falling for him.
Ryan comes up to Tessa and Lisa and salutes Tessa, and says, "Good day Ms. Altman." Tessa asks him what's wrong with him. And he replies that he wasn't sure if she was ready for everyone to know that they are officially a couple. She says she doesn't care, and he announces in the school hallway that they are in love and are dating. A couple of Ryan's friends come over and high-five him.
Tessa and Ryan fight about their school team losing the football game, because they weren't able to run through paper. Ryan then blames Tessa for not wanting to fit in with his friends. He then tells her that she's always trying to make people think. She replies she thought that was why he liked her.
Towards the end of the episode, Ryan apologizes to Tessa about being a jerk earlier. He realized that Tessa's never had anyone cheer her on before, so him and a couple of his friends make a 'Go Tessa' banner and she runs through it into her classroom, a little bit embarrassed, but happy nevertheless for the thought.
In this episode Tessa and Ryan go on a double date with Lisa and Scott Strauss. Ryan asks Scott how he gets his hair so smooth and good looking. He then asks if he can touch it as he just can't resist, he says yeah, no problem, so he touches Scott's hair and just sighs - then tells Tessa to leave him for Scott. That he'd absolutely understand why, and that they'd make a perfect couple. Tessa insists no way, then she kisses Ryan on the cheek.
Tessa is put in charge of the Chatswin High School TV show 'Teen Talk'. Ryan decides to take over when Tessa can't get enough ratings, so he can hang out with his girlfriend more. He mostly talks just about his body and his workout regime, which upsets Tessa that Ryan is using her/the TV show to talk about something so superficial. She then gets into a big fight with him and he calls her a loser because she doesn't have as many friends, and participates in zero school activities. Tessa then fires Ryan from 'Teen Talk', and he storms out in a huff.
After realizing that the show is failing once again without Ryan, Tessa decides to bring on a special segment: Her talking about Ryan's body. A caller rings in asking Tessa what her favorite part of Ryan's body is. She instantly says that her favorite part is undoubtedly his heart. Ryan hears this, and immediately rushes out the door to her. He comes in, and apologizes for calling Tessa a loser. Tessa in turn says she's sorry that she was acting like one. The two of them reconcile and kiss.
Blowtox and Burlap
Tessa and Ryan go to see an arthouse movie. While Tessa doesn't understand the movie, Ryan surprisingly seems like he was really into it, and even understands the different ideas involved with the film. When the film ends, Ryan walks away from Tessa because he "feels like walking the earth".
Tessa then shows up at a classmate's party. She sits down on the couch, and they discuss about how he liked the movie and she did not - not what she had expected. She then says maybe that's what makes them a cool couple, that they are unpredictable. He agrees... then adds, it's also because they're both super good looking. Then they share a kiss.
Tessa found out that Ryan lied to her in the previous episode about going to an away game for three days. She's upset with him, and he tries to explain to her that he's being pursued, not by girls but by colleges. Tessa isn't sure how to feel about Ryan leaving her behind.
Ryan and Lisa are sitting outside a frozen yogurt shop in Chatswin, and Ryan talks to Lisa about how he thinks that Tessa is breaking up with him, even though she didn't say it "with her words". Ryan then asks Lisa if he should defer for a year and stay in Chatswin so that way when Tessa goes to college, they can go together. Lisa then tells Ryan that that isn't going to work, because Tessa will most likely attend a college that values the curious mind, creativity, hard work, and intellect ... and Ryan is mostly likely to attend the University of Florida.
Ryan shows up at Tessa's place, and tells her that he doesn't want to scare her off by bringing up the 'L' word. But then proceeds to tell her that he loves her, he's in love with her, and he loves loving her. Tessa asks Ryan which L word he was talking about then, and he replies by saying 'Leaving'. He then tells her that he has a plan to keep him in Chatswin. Tessa asks him, "Ryan, did you do something stupid?" He replies, "I think we both know the answer to that."
Ryan then gets Jarrison, the photographer who took their holiday pictures, to hit him in the leg with a metal pipe. Tessa tries to call Jarrison before he breaks Ryan's leg, but only reaches his voicemail instead. Jarrison comes out of the bushes and tries to break Ryan's leg, but Ryan says that he's still all good, his leg isn't broken. Jarrison then tells the two of them that he's having a special at the photo shop, and that there's going to be a special for wallet sized prints. Tessa asks Ryan if he wants a wallet sized picture of her to take to college, and he replies he'd rather have a life-sized one of her to take with him to college.
Ryan's trying to decide on which college he wants to attend. He can either go to college near Chatswin, or he can go to Florida, as Florida's always been his dream school.
So Tessa tells him she's going to put all the college's names into a hat and do a random drawing. But she rigs the drawing, by only putting in Mid Florida Tech's name into the hat.
At Ryan's press conference, he announces to the school that he's going to be attending college in Florida. Dalia then reveals to Ryan that Tessa rigged the drawing by putting the same school/name on all the pieces of paper, into the hat.
Ryan and Tessa are in his room, after Dalia tells Ryan what she knows, and Tessa asks Ryan to not be mad at her, as she did it for him. That the only thing standing in his way was her. Ryan replies that he's mad at her because she choseto send him away, instead of keeping him close to her, that was what hurt him the most, and not that she deceived him.
Ryan then breaks up with Tessa, by telling her, "We're over." Tessa goes home crying. Lisa comes over and tries to comfort her, and Tessa asks Lisa who could have told Ryan. When Lisa doesn't respond, Tessa knows something's up. She realizes that it was Dalia, and utterly furious says, "How about you warn her about me. Because this time she messed with the wrong bitch!"
Tessa is living in the Chatswin high school handicap restroom, (because, in previous episode, George had announced that he and Dallas were moving in together. - Tessa replied that there was no way that she would ever live under the same roof as Dalia!)
While she's coming back to the restroom, after getting some snacks from the vending machine, she encounters Ryan in her stall. After a short talk with him, about how he thinks it'll be much easier for him to leave for college, now that they're no longer in love - he then walks up to her, and presses her up against the wall. They start to kiss... (and it's then indicated that the two of them finally have sex, as a goodbye to each other.)
Catch and Release
Tessa feels like she shouldn't have let Ryan go without a fight, so she gets Dalia to help her get a ticket to go to Florida to see him. When she gets to the Shay's house to get Ryan's dorm infomation, June, Fred, and Sheila are there, and they're planning on going to Florida before his game to cheer him on. Tessa realizes that she can't go to Florida when June and the Shays are going to be there as as well.
It's Lisa and Malik's wedding night, and Ryan has come back home, to see his little sister get married. While Tessa is getting the Shay's backyard all set up, Ryan walks up to her, and they talk in French - because it's romantic - even though Ryan doesn't speak French.
June interupts them, and drags Tessa into the bathroom. June tells Tessa to back off of Ryan because he's with her now, and not with Tessa.
During the wedding dance, she sees Ryan and June dancing. Tessa realizes that Ryan is no longer with her, and is now with June, and that it's still painful for her to see him with someone else. She starts to cry, and this proves that Tessa still has feelings for Ryan.
In this episode Tessa comes up to Ryan, while he is packing up his car to go back to Florida, and says that it's good that the two of them are so cool with each other, after their break up. She then proceeds to walk away, and back into her house, to the old knitting women who are hanging out with her.
But apparently Ryan doesn't feel the same way, and Tessa realizes that Ryan might be the wound that will never heal. She runs out of her house, as Ryan runs down his driveway - and they meet in the middle of the street. They embrace, and start kissing. It is at this point that Tessa takes off Ryan's shirt, and hoodie.
Sheila and June are sitting in the Shay's living room, and when Sheila witnesses Ryan & Tessa in the middle of the street kissing, she gasps! - and quickly draws the window curtains, to avoid having June see the two of them together.
They two continue kissing, as Tessa wraps her legs around Ryan and he takes her top off.