It wasn't long before Dipper was discharged from the hospital. His back was still very sore, and he had to wear a back brace. Because of this, he couldn't move as fast as he would like. As soon as he walked through the mystery shack door, Mabel greeted him by blowing a party horn. "It's great to have you back Dipping sauce" said Mabel. "So, has Wendy finally told you?" "Told me what?" asked Dipper. "You know, I could have sworn she would have told you by now" said Mabel. "I've been trying to convince her all summer."
Dipper then walked into the gift shop area of the mystery shack, where Wendy was sitting at the counter. Her boots were on the table, and she was reading a magazine. "Wendy, is there something you want to tell me?" asked Dipper. Wendy noticed that Dipper was speaking to her. Instead of acting nervous like she usually did when Dipper was in her presence, Wendy had a genuine smile on her face. After spending more time with him, Wendy began to feel more confident about herself. She was no longer nervous, and decided to give Dipper the truth. "Dipper, i'm in love with you." Dipper was surprised by what he was hearing. "Okay, this is the last thing I expected to hear" he said. "Throughout my life, I have always felt very awkward around girls." "They always saw me as weird, and I was always too nervous to come near them." "Never once in my life, has a girl said that they had romantic feelings for me." "I never expected that girl would be three years older than me." "You're a nice person Wendy, and if I never came here this summer, I wouldn't have met you." "I think i'm willing to give you a chance, we'll see where this relationship thing goes after a week or two." Wendy could not believe what was happening, Dipper was actually saying yes, in a way. The two of them were now boyfriend and girlfriend, for now.
The following day, Stanford was throwing a party at the shack. There wasn't any particular occasion, the party was simply happening so he could charge admission for people who wanted to attend. Originally, Mabel and Wendy were going to be standing outside the shack collecting the admission money. Seeing as how Mabel really wanted to make new friends at the party, Dipper offered to switch places with her. As he and Mabel were sitting in their bedroom getting prepared, Dipper began to feel nervous. "I don't how this is going to turn out, i've never had a girlfriend before" said Dipper. "You'll be fine, just don't overthink things like you usually do" said Mabel.
As Dipper and Wendy were sitting outside handing out tickets, Wendy felt happy, while Dipper felt awkward. "So, how about you come over to my place tomorrow night for dinner?" said Wendy. "Oh um, yeah, I guess i'm available" said Dipper. Wendy just chuckled. "Okay seriously dude, why is it that you have trouble with girls back home?" she asked. "I really don't want to go into detail, it's way too embarrassing" said Dipper. "Yeah you're right, too early in the relationship to get personal" said Wendy. While Wendy could have easily asked Dipper to cover for her while she went inside to enjoy the party, she decided to stay outside, with the man she was positive would be a keeper. The only time she left the table, was when she had to go to the bathroom. While the two sat outside together, they got to know each other even more. Once the party was finally over, Dipper felt exhausted. It was midnight, and his back was still hurting from his injury. "Well, I guess i'll see you tomorrow at your place" he mumbled. He then slowly made his way back into the shack.
Authors note: Now that the main pairing of this story is officially a couple, things are going to get interesting from here. There are going to be some pretty significant changes, and some of them will unfortunately not be pleasant.
Even without the crush on Wendy, it's very easy to assume that Dipper would still feel awkward about the concept of a relationship, when you take his character traits from the canon show into consideration.
Thank you for reading and please have a great day.