Zoro wasn't going to lie, he had been lonely after the first 3 months of his traveling. The first place he visited was the rest of Japan. Being that he was using this time to relax, he only used Plaines to get to the general area before exploring everything. He also came to know that he didn't like the city life.
At first it was fine, but a week or so In and he had become irritable, snapping at people that were just minding their own business. After yelling at a crying kid on a train, he figured that because of his enhanced senses, he was experiencing more sensations than he was used to, becoming more irritated at everything.
By the first month he had gotten used to it, after that he mainly stuck to rural areas to acclimate himself. Despite how irritated he was, he was also having the time of his life! The scenery, food, and general atmosphere of the places he was visiting were fantastic.
He started with Japan, before moving to the rest of Asia. His schedule would take about one year per continent. He would only be going to six out of the seven. Staring with Asia before moving on to Africa, then Europe, then south America, then north America and then ending with Australia.
The first year was the hardest, calling his grandmother to check out what was happening while also keeping in touch with Rumi, he started to really appreciate the company they provided. It was a stark contrast compared to his first life where all he did was work, sleep and eat, to be able to live. His family also was full of scumbags that wanted what others had but weren't willing to work for it. Zoro would still visit once a year so that he doesn't get homesick too much. He was really glad to have started the trip. Even though He and Rumi were so far apart, they still built their relationships to be best friends.
He wasn't worried about dating right now and neither was she. She had started UA recently so she didn't have much time to talk but they made time for themselves. Zoro also started to gather a following about 3 years in when he was in Europe, throughout his travels he also helped people out when they needed it, creating alot of houses and other essentials for the homeless.
He also helped out mutant quirk users the most because they were shunned by society and he knew how they feel. When he was visiting London he came across another dragon quirk user that was living on the streets. After buying her some food, zoro asked for her name and why she was homeless. Answering back the kid said her name was Artoria and that she has always been homeless, only surviving thanks to her quirk. He asked what her quirk was and she said it was called dragon soul, a quirk that gives the user massive amounts of energy at the cost of being more wild and violent as the energy depletes.
When asked what she was gonna do, Artoria said that she doesn't know, but that it gets harder to control herself because of the low amount of food she is able to find. Zoro thought about it for a moment before asking if she wanted to come with him. He knew that she would most likely either die from starvation or would go crazy and turn into a villain. He didn't want either of those to happen so he asked.
Taking a moment to study him, Artoria finally said yes after 5 minutes of waiting, but she added that zoro had to train her while she was with him. She could tell that he was strong, the dragon inside of her was practically whimpering from being near him. Zoro was perfectly fine with that but said that should she not give it her all he would leave her behind. After getting clothes and other necessities for her, they were ready to go. Zoro wouldn't know but he would become famous as a teacher from this encounter.