|“|| Stefan: Caroline. You have been my... my friend, my conscience, my sounding board. You saw light in me when all I saw was darkness. You saved me from despair. You told me once that I would fall madly in love without realizing it. And that's what happened. Day by day, bit by bit, year by year. With you.
Caroline: I remember saying that to you. We were dancing at my prom. It's funny the things we remember out of all the years that go by. I remember how you told me that when I was ready for you, you would be ready for me. I'm ready now. I think a part of me has been ready for this day since the moment I first saw you, the new mystery guy in the hallway at school. I will always remember this moment. A hundred years from now, I will remember this moment for the both of us.
Their relationship at first wasn't very strong. In Season One, Caroline felt an attraction for Stefan, but he rejected her immediately because he was interested in Elena. Later Caroline started dating Stefan's brother, Damon. Stefan saves her after Damon attempted to kill her. Shortly after, she started dating Matt, Elena's ex-boyfriend. In Season Two, their relationship changed due to Caroline's transformation into a vampire. When Damon was about to stab Caroline, Stefan stopped him, promising her that he would never let anything happen to her. He became her mentor, teaching her how to control her emotions and thirst for blood. In one conversation, he told her that she reminded him to his best friend Lexi who was killed by Damon.
Stefan comes across as quite protective of Caroline throughout the series. They became good friends in Season Three in spite of little screen time together. They became really close by Season Four. Caroline told him that every time he feels he's about to lose control she will be there for him and they have given each other pivotal emotional support on many occasions. Notably, they have always been able to help each other with the other's relationship problems. Caroline always supported his relationship with Elena up to the point where she herself developed romantic feelings for Stefan. She was the person who revealed to Stefan both that Elena was sired to Damon and that Elena had slept with Damon. Stefan, on the other hand, comforted Caroline during the emotional fallout of her sleeping with Klaus. Stefan and Caroline share their secrets and always help each other. In Season Five, when Stefan lost his memories due to a spell, Caroline was the only person that he trusted immediately and he also blatantly flirted with her on at least one occasion, telling her she was "much hotter in person". After regaining his memories, when Caroline believed that him and Elena were getting back together, she seemed quite jealous, which was a drastic departure from before, when she always supported their relationship. Upon learning of Bonnie's death, Stefan told Caroline that he would always be there for her as she has always been there for him.
In Season Six, Caroline and Stefan haven't seen and spoken in four months after the death of Bonnie and Damon. Stefan didn't answer her calls and she did her best to find out what's up with him. Enzo found Stefan and took Caroline with him. She was upset that Stefan had decided to move on with his life and try to forget all about the old, Damon's death and her. After a while Stefan became aware that Caroline's feelings for him had turned romantic and made several attempts to reconcile, but their friendship remained strained. After her mother was diagnosed with cancer, Stefan stuck by Caroline through her grief and they made up. Their friendship deepened, culminating in a kiss, but Stefan was unsure of how to move forward, given the fact that Caroline's mother had just died, and Damon had planted doubts in his mind.
During Caroline's mom's funeral ceremony, Stefan overcame the doubts in his mind and realized that he had developed deep feelings for Caroline - referring to it as being potentially "something even better" than his previous romances, even if he could not quite define them - but after the service, he arrived at her address too late to tell her since she had already flipped her humanity switch in order to cope with her mother's death and in the belief that her love was unrequited. Stefan reached out to her - realizing that he is Caroline's trigger back to humanity - but was backed into a corner and forced to turn off his own when she attempted to kill his niece, Sarah Salvatore. Afterwards, Stefan, without his humanity, terrorizes Caroline and forces her to "lose control" and give into her murderous impulses as a form of revenge for burdening him with guilt when his humanity comes back. Stefan succeeds and after feeding on a bystander victim together, the two have sex for the first time.
In Season Seven, they decide to give each other space while Caroline grieves the death of her mother and tries to move on. Stefan and Caroline team up against a new threat in Mystic Falls, The Heretics and while boarding up Caroline's house, the two share a moment. Caroline later gets kidnapped and taken by Enzo who was following orders from Stefan and Damon's mother Lily. Stefan makes an attempt to save her but fails due to the fact that Damon bailed at the last minute. Stefan then confronts Damon angrily. Valerie casts a spell on Caroline which turns her skin to vervain making it hard for vampires to harm her.
Caroline then discovers from Nora after she gives Caroline Stefan's old journal that Stefan was romantically involved with Valerie, a Heretic. Caroline gets released by Lily but still had "vervain skin". A few days later, Stefan and Caroline still cannot make physical contact and try to convince two of the heretics, Mary Louise and Nora, to siphon the spell off of Caroline. They decide to attend The "Heaven and Hell" ball where they force Nora to siphon the spell off of Caroline after threatening Mary Louise's life. Stefan and Caroline then kiss and have sex for the for the second time.
After being apart for three years however, their relationship is tested being Stefan has been on the run with Valerie Tulle for three years. After going on the run together when Bonnie Bennett turns into the next Supernatural Huntress, Caroline and Stefan bond and maintain a new friendship. After Gods and Monsters, Alaric and Caroline break up being her heart truly belongs to Stefan. Caroline and Stefan talk, sharing a kiss together. Currently, Stefan and Caroline are dating once again. Shortly after this, Stefan proposes to Caroline and she accepts his wedding proposal; they are currently engaged as of Season Eight.
The friendship and romantic pairing is known as "Steroline" by the fans.
Throughout The Vampire Diaries Series
On the first day of school, Caroline expressed interest in Stefan who was the new and mysterious student. She invited him to a back to school party, and he accepted because Elena was going. At the party, Caroline tried to get his attention but he rejected her and went to spend time with Elena, offending Caroline who felt that every boy she liked would always like Elena. However, she met Damon, Stefan's brother and got over Stefan.
Stefan disapproved Damon's involvement with Caroline and how he fed on her and played with her like she was a puppet. Damon ignored him and Stefan worked with his nephew Zach Salvatore to stop Damon, spiking Caroline's drink with vervain. After Damon's disappearance, Caroline was disappointed to learn from Stefan that Damon wasn't coming back.
Damon compelled Caroline to free him from his prison and killed Zach, much to Stefan's horror. He told Damon to leave Caroline alone when she planned a party at the Mystic Grill.Elena and Stefan. She didn't feel that the date was going the way she had planned. Realizing this, Stefan decided to give her some time with Matt and he let the two drive his car.
Both Caroline and Elena took part in the Miss Mystic Falls Pageant with Stefan and Matt as escorts, but both guys had to be replaced. Stefan and Caroline were also on the float on Founder's Day. Tyler Lockwood, Stefan, Damon and several other vampires were affected by the device. Tyler drove off the road and Caroline was injured in the accident.
In The Murder of One, Stefan and Caroline make a plan with Elena, Matt and Damon to kill the Originals.
In Do Not Go Gentle, Caroline encourages Elena to ask Stefan to be her date to the 1920s school dance, to which Elena reluctantly agrees. During the dance, Stefan informs Caroline that they are trapped there with a boundary spell. Caroline tries to reassure Stefan because he's worried about Elena.
In Day One of Twenty-Two Thousand, Give or Take, Caroline is sitting in the town square when Stefan approaches they make small talk and his admits that his previous confession had made things between them awkward and that he wanted to be friends with her so they should just stay friends if or until she wanted more. Caroline helps Stefan in his plan to kill the heretics tries to discourage her from doing but she reminded him they knew what he looked like so he couldn't do it. After successfully delivering the bomb that fails to kill the Heretics, Stefan and Caroline are in the time square for Matt's graduation from the police academy when the heretics attack killing half of Matt's class. Afterwards Stefan and Caroline go to his house and discuss what had just happened, while they dio Caroline helps Stefan remove a small splinter from his neck. Caroline helps Stefan broker a peace settlement with his mother, they handed over his house and compelled all the residents to leave and restricted the heretics from feeding on anyone besides anyone who wandered into town. Stefan helps Caroline box up her house and they talk about the newest situation they'd gotten themselves into, just as Stefan was about to leave Caroline tells him she wants to make a go at a relationship with him and they kiss.
In Never Let Me Go, a flash-forward is seen in which Caroline professes he distaste when she hears the mention of Stefan's name saying she never wanted to hear it again. Back in the present Stefan calls Caroline and she doesn't answer he leaves a message, he is approached by Lily and Beau who inform him that they had taken Caroline. Stefan enlist Damon's help in getting her back, Damon goes to the boarding house and tries to plead his case with Lily, after she refuses to return Caroline Damon discovers that the house had been signed over to a human who they discover to be Matt. Bonnie does a spell that temporarily kills him allowing Stefan and Damon to enter the house without an invitation, Damon goes in through the front door to distract Enzo Stefan goes in through the tunnels and begins looking for Caroline finding her in his former bedroom. When Caroline first sees him she believes she is hallucinating, Stefan goes to her side and brakes her chains when he attempts to carry her out his skin burns from a spell, Valerie, One of the heretics had put on her. Stefan finds her a jacket and helps her put it on, they both suddenly start feeling a strange pull and is pulled out the window while Caroline begins to be pulled toward the front door. Enzo is standing at the bottom of the stairs with Lucy and has her invite Caroline inside which stops the pulling. Nora comes into speak to Caroline and tells her that Valerie's spell wasn't in fact to help her but that Valerie had a past with Stefan and had been carrying around his journal from 1863 since 1903. Caroline taked=s the journal and begins to read about that had happen between Valerie and Stefan in 1863.
In Age of Innocence,
In Live Through This, Caroline helps Valerie plan her new identity because she knew Stefan wanted to help her out.
In Best Served Cold, Valerie reveals that to Caroline that she had been pregnant in 1863 and that Julian had killed it and she knew the spell the Gemini Coven had been chanting because she had attempted to use it to save her child.
In Mommie Dearest, Caroline tells Stefan about her pregnancy with Alaric's children and Stefan leaves to go kill Julian.
In Things We Lost in the Fire, Stefan explains that the only reason he was holding it together after his time in the phoenix stone was because Caroline was there for him.
In Postcards from the Edge, Stefan brings Caroline food and she suddenly collapses he brings her to the hospital and Valerie meets them there and tells that the babies were siphoning Caroline's magic she give Caroline an amulet to keep the siphoning at bay. Stefan receives a call from Matt saying that Damon was hanging out with Julian, Stefan is reluctant to leave but Caroline tells him to help his brother. Later after i took a while for his to return she sends Valerie to help him, while they were gone the babies began to siphon making her unable to mobe to call stefan for help.
In This Woman's Work, When Stefan arrives back at the hospital he has her rushed into to surgery to get the babies out before they killed her,compelling the doctors to ignore anything not explained by science, but the babies repel the doctors when they try to take them out. Valerie gets the other heretics and they begin preforming a spell to trick the babies into wanting to come out. While the doctors to the surgery Stefan gives Caroline a vision that they are sitting under the stars on date. Bonnie comes in and tells him that the huntress is there and Damon was being suicidal and he had to help him, Stefan reluctantly leaves to help his brother. Stefan begins to help his brother fight the huntress and gets marked by her. When he gets marked Stefan remembers all the good times he'd had with Caroline and how much he loved her but also Nora's word that once marked she would chase him to the end of the earth. He leaves to keep his family safe Damon calls him and he yells at him because it was his fault wasn't able to be with Caroline her time of need. Next Caroline calls and they take sadly about their predicament how they wish it didn't have to be that way.
In I Would for You,
In Gods and Monsters, Caroline and Stefan finally set aside their tension due to their dating-history and work together to help Bonnie escape from her Supernatural Huntress side. They have been on the run together and they decide to halt their running when Caroline reunites with Alaric and her children. Caroline assists Alaric in teaching the twins about their Siphoner heritage, which they grasp easily. Stefan watches from afar as Caroline successfully mentors her children in opening the Armory doors. After successfully saving Bonnie, Caroline hugs Alaric and Alaric advises her to go after Stefan. Caroline originally protests being her family is on her mind. Alaric claims that they will still be a family and Alaric and Caroline break their engagement off on friendly terms. Caroline rushes up to Stefan before he leaves the Armory property and she kisses him. Thanks to Alaric's pushing, Stefan and Caroline are dating once again after being apart for three years.
In Hello, Brother, Stefan and Caroline are first seen together having passionate sex. This episode shows that they are still together, months after the events at the Armory. However, the scene is quickly cut off to show Enzo and Bonnie's flashbacks.
Later on, the morning after their night together, Stefan and Caroline are lying together in bed discussing their stressful lives. Caroline complains about not being able to hold a stable schedule to watch her children, especially with Alaric working with a team to investigate the Armory's vault. Stefan also explains the constant stress of failing to find Damon and Enzo, he also explains that it has taken a toll on Bonnie as Stefan and Bonnie constantly fail in trying to find them. They later, in the episode, part ways and deal with their own situations related to family problems: Caroline was dealing with Virginia St. John invading her home and trying to take her children to stop the Armory's monster, and Stefan with finally finding Damon and Enzo with Bonnie, it brings him hope about all their futures.
In Today Will Be Different, Stefan and Caroline only interact with each other at the end of the episode. Stefan was devastated after losing Damon and Sarah Nelson to Sybil's mind manipulation. Caroline also had a long day dealing with her children's lives and comforting Bonnie after Bonnie lost Enzo too. Stefan and Caroline embrace each other and reveal to each other that they are like family now, considering Stefan built a room for the children whenever Stefan and Caroline were together with them. Shortly after, showing Caroline a new set of drawers for the children's new bedroom, Caroline opens one of the drawers and is shocked to find a black jewelry box. Both with tears in their eyes, Caroline accepts Stefan's marriage proposal and they have a passionate embrace together.
In Coming Home Was a Mistake, Stefan and Caroline are first seen together in their house. Matt's number then appears on Caroline's phone. Later on, Caroline and Stefan are seen together attending Tyler's funeral. However, this is interrupted when Damon crashes it. Caroline and Stefan beg Damon not to kill Matt when Damon puts Matt in a chokehold. They eventually get through to Damon and he lets Matt go. Later on, Stefan convinces Caroline to stay home when Stefan goes to meet Damon. However, when Damon and Stefan get into a fight at the carnival, Caroline shows up and saves Stefan from death by shooting Damon with a vervain gun. Caroline and Stefan are later hanging out together with the rest of their friends at the carnival. Caroline tells Stefan that she is going to be his wife soon and that she will always have his back in situations like the one they went through together earlier, with Damon. After sharing a moment, Matt reveals to them that Seline (Lizzie and Josie's babysitter) is the second siren. Caroline leaves the carnival with Alaric, with Stefan not too far behind, to find just a drawing at their house with Lizzie and Josie with Seline and Cade.
In We Have History Together, Caroline and Stefan do not interact in this episode. However, Caroline mentions to Matt, while on the phone with him, that she hasn't seen Stefan in three weeks, due to his deal with Cade. However, Caroline states that she misses him and later, tells Sybil that she is confident she will be reunited with Stefan. Caroline is concerned however when Sybil spitefully claims that Stefan always seems to "fall off the wagon" and worries Caroline when she explains that Stefan might turn into a ripper in front of her kids, sometime in the future.
In What Are You?,
- Stefan: Rebekah is our target so we distract her and catch her off guard. To do that we need to keep Klaus separate and occupied. (Stefan looks at Caroline.) Caroline.
- Caroline: Why do I always have to be Klaus bait?
- Damon: Because he’s obsessed with you.
- Caroline: I miss well-adjusted Stefan.
- Stefan: It’s the blood. The bloodline. It has to be. Think about it: Finn turned Sage, Sage turned Troy. They’re all part of the same vampire bloodline that originated with Finn.
- Caroline: Wait, so when an Original dies every vampire turned from their bloodline dies along with them? Because that would mean…
- Damon: If the Originals die, so do all of you. The entire vampire species would… it’d just be dead.
- Stefan:We have no idea. But keep your eye out for anything that might be weird, They're at the old cemetery. Jeremy and Matt are headed there right now.
- Caroline: You let them go?! They're gonna get themselves killed!
- Stefan:We have no idea. But keep your eye out for anything that might be weird, I didn't have a choice, Caroline. We're useless right now stuck in here.
- Caroline: Hey, she'll be fine. Elena always manages to find her way through this stuff.
- Stefan:We have no idea. But keep your eye out for anything that might be weird, Yeah, well I'm just as worried about what Esther is up to. She lead Klaus here for a reason. If she succeeds in whatever she's doing.
- Stefan: Marry me. I don't expect you to believe that I'm sorry, or that I love you because I say it. I need to show you. Marry me.
- Caroline: I thought you had to figure things out.
- Stefan: I did. I figured out that I'm an idiot. I'm intellectually challenged, maybe even blind. I couldn't see that everything that I was looking for was right here in you. I have a lifetime of work to do to make things right, but I can't imagine doing it without you.
- Caroline: No! No. I don't want to let go of you. But you're human now. Do you know what that means?
- Stefan: It means I get to grow old with my best friend. It means I get to help my wife raise her two beautiful children, and their children after that. It means I get to fight to be the man that you deserve, until the day that I die. I love you. Will you marry me?
- Caroline: Yes. Yes, of course.
- -- It's Been a Hell of a Ride
- In the books, Caroline competed with Elena for Stefan's affection.
- Stefan was the first of Caroline's love interests in the TV series, but her romantic interest in him only lasted one episode.
- Stefan promised Caroline not to let anything bad happen to her.
- Caroline never saw Stefan's evil alter ego, "Ripper Stefan", firsthand.
- It is suggested that their frienship might turn into romance in Season Six.
- Stefan sees her as his new Lexi.
- Caroline is Stefan's best friend.
- Caroline is Stefan's sober sponsor.
- Even when Stefan had no memory, Caroline was the one of the only people he trusts.
- Stefan thinks Caroline is hot and Caroline thinks Stefan is smoking hot.
- Paul Wesley likes "That Steroline Business".
- Caroline showed jealousy towards Elena, because she thought Stefan and Elena were secretly hooking up.
- Caroline was the last person Stefan was with when he died, cradling his head on her lap as she cries of help in sheer anguish.
- Lexi, Damon, Elena and Alaric support them.
- Lexi thanked Caroline for keeping an eye on Stefan when she was on The Other Side.
- Fans refer to them as 'Steroline'.
- "It’s a very slow build for them" - Caroline Dries about Stefan and Caroline.
- She admitted her feelings for Stefan in Welcome to Paradise.
- In I'll Wed You in the Golden Summertime, Caroline reveals that she fell for Stefan the summer he went missing after Damon's death.
- She called Stefan a "dick" in Yellow Ledbetter, for the first time.
- She lost her patience in The World Has Turned and Left Me Here and told him to leave, however she seemed like regretted what she said. Stefan left after her words and then went to the Salvatore Family Crypt.
- When Damon returned, Stefan instantly wanted her friendship back but Caroline turned him down with these words "I don't want to be friends anymore" in The More You Ignore Me, The Closer I Get.
- "It's just a slow burn" Paul Wesley about Stefan and Caroline's relationship.
- "He really cares about her (Caroline). He really loves her. That's not even a question." Paul Wesley about Stefan and Caroline's relationship.
- Their relationship seems to be a friendship developing into a passionate love.
- "It feels like we are slowly but surely earning a romantic relationship." Caroline Dries about Stefan and Caroline's relationship.
- Stefan found out from Enzo in Do You Remember the First Time? that Caroline had a Thing for him.
- They kissed for the first time in Stay.
- Stefan admitted to Damon in Let Her Go that he had feelings for Caroline that he couldn't explain.
- Stefan admitted to Caroline in The Downward Spiral that he likes her after she turned her humanity off.
- Humanity off Caroline used the life of Stefan's great-niece Sarah Salvatore in The Downward Spiral to force him to switch off his humanity, as she realised that he was her humanity trigger.
- "I think Caroline has progressed as a character and I think he[Stefan] has fallen in love with that person she has become" Paul Wesley about Stefan's feelings for Caroline at TVD Atlanta Con.
- Stefan and Caroline have sex for the first time in A Bird in a Gilded Cage
- In 2015, they won the E! Online Top Tv Couple Tournament 
- In Never Let Me Go, it's revealed that in the future they are no longer seeing each other and Caroline is engaged to someone else, and in Best Served Cold, It revealed that she's pregnant with Alaric's children's and in the future she's engaged to him and a mother to Josie and Lizzie Saltzman.
- Stefan and Caroline said "I Love You" for the first time in Hold Me, Thrill Me, Kiss Me, Kill Me.
- In Gods and Monsters, Stefan and Caroline enter their second, romantic relationship after being broken up for three years.
- During their time apart, they couldn't get over each other.
- Stefan and Caroline decided to move in together in Hello, Brother.