When she first properly met and talked to him, she was at a dark place because she just had the worst year ever, with all the bulls that tried to bring her down, and they did for a while make her feel like she’s the worst person in existence, but after Jiyong came to her life, she learned to not give a about those things anymore, and with Jiyong, she was able to pick herself up and be a better person, so when Jiyong finally confessed that he loves her, at first she was scared, but Jiyong tells her that it’s okay to be scared, because he was actually scared too about confessing to her. Taeyeon actually decided to be hard on him when he first confessed his feelings towards her, then finally she accepts him as her boyfriend while being very cautious at the same time. The first few weeks of becoming Jiyong's boyfriend. Taeyeon decided to be a cold girlfriend towards him when in reality she was actually very shy and always blushes really hard that her entire body was turning red because Jiyong never forgets to show his love and affection towards her by doing skinship and saying "I Love You" to her everyday and because of that Taeyeon was having a world war on her mind until finally the inner self war ended with Cold and Coward Taeyeon finally losing and Real Taeyeon winning. After a while, she finally decided to be brave about her feelings to the Dragon, and Jiyong was so happy when he first heard those 3 words coming out of .

After almost 3 years of dating, it was when Jiyong is preparing to enlist to the military, Taeyeon finally makes one of the most hardest decisions in her life, Taeyeon finally decided that she will give herself to Jiyong because she wanted him to know that she has never done this before, and she trusts Jiyong enough for him to take her ity, at first when Taeyeon told Jiyong that she wants to do “IT”, Jiyong was instantly taken aback and flustered so much that he almost had a panic attack, but Taeyeon reassures him that she wants this and this is her gift to him, so on the night of February 26th 2018, Taeyeon and Jiyong finally joined as one as they made love throughout the night, and finally when the time comes for Jiyong to serve his country, Taeyeon couldn’t stop crying and so is Jiyong because they’re both will miss each other so much for almost 2 years, so when Taeyeon sees Jiyong disappeared into the crowds of the newly enlisted men, she couldn’t stop crying like a baby and for a few weeks after that whenever she’s alone in her house, all that she can do was crying herself to sleep, and she would wake up and cry again, and this got the attention of her members and also Seungri who’s always by her side since Jiyong enlisted because Jiyong told him right before he enlisted to take care of her, so they tried their absolute best to keep Taeyeon’s mind occupied long enough for her to forget about missing Jiyong, they did that by taking Taeyeon on a trip whenever she’s free, and they definitely succeed at doing that, because they see that Taeyeon is starting to be happy again because Seungri told Jiyong that Taeyeon is still crying everyday because she misses him so much, so Jiyong decided to ease her pain by writing many letters talking about his military life, and so they both exchange letters to each other to try to lessen their longing for each other.

After almost 2 years of waiting, on October 26th 2019, Jiyong finally got discharged, and he’s very excited to meet the love of his life after an agonizing 1 year 8 months of only exchanging letters to each other, but Taeyeon doesn’t know about his early discharge, because she still thinks that he will be discharged on November, so when Jiyong found out that she doesn’t know about his discharge, he immediately comes out with a plan for surprising her, because Taeyeon is currently in New York