Ari - If she knows he likes her, it'll be awkward when she's still getting tattoos from him during those 2-3 years. And she probably wouldn't vent to him about her guy troubles (she always does while he's designing and drawing the tattoos on her), which is key in the fact that if she can trust him with the tattoos/her personal love life, she can probably trust him not to break her heart. Baby steps pretty much. And if she doesn't get tattoos from him, she can easily ask his sister (the real tattoo artist) who lives two hours away. It's worth it since she's passionate about getting these tattoos.