Dipper is shown to usually be nervous around Wendy. But he can be brave too, if he just goes for it without thinking twice. This is foreshadowed in Tourist Trapped, when Dipper just runs up to Wendy and tells her what he wants.
Dipper's nervousness around Wendy is first shown several times in The Inconveniencing. The first of which was Wendy and Mabel's "random dance party for no reason!"
Even with Dipper's crush, he and Wendy are still good friends. This is showcased in many episodes, most notably in The Inconveniencing.
Wendy may know of Dipper's crush on her. The first evidence of this comes in The Deep End, when Soos mentions Dipper and Wendy's "secret staring contest" and Wendy gives them a strange look.
Wendy may be dating Robbie for a large chunk of the first season, but she still doesn't like it when he is condescending to Dipper. This is shown in The Inconveniencing, when she rebukes him for his comment that she is babysitting, and in Boyz Crazy, when she gets mad at him when he insults Dipper openly.
There's also evidence of Wendy possibly knowing about Dipper's crush on her in Gideon Rises, when Soos outright mentions Dipper's humongous crush on Wendy...in front of her.
In Fixin' It With Soos - Golf Cart, Wendy and Dipper are hanging out for the fun of it. It helps to show their friendship, even though they are not involved romantically.
A few seconds later, Dipper asks Soos (with Wendy in the background) if the jump suit looked good on him. Soos seems to disagree.
Finally, this relationship came to a climax in Into the Bunker. Obviously, this entire episode dealt with Dipper's crush on Wendy. They used Mabel's advice, "if it feels like you two aren't the right fit, force it!" The episode basically pointed out everything on this page, which virtually renders it moot. I even considered deleting this page briefly, but I've decided to keep it.
It's a good thing I decided to keep this page. Blendin's Game brought the topic back up again. Notice that Wendy carefully avoids talking about her own feelings towards Dipper in their conversation from Into the Bunker. Will it happen outside the scope of the show? If the two get together, will they stay together?
