These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
Hollywood Homely: In a male example, any woman would have to be blind to think Jensen Ackles, even with a mohawk and piercings, is supposed to be some sort of weird punk-rock oddity that Tish wouldn't give the time of day to.
It seems more like he wanted to look nice just to ask Tish out, rather than have it be his permanent style. In the final couples lineup scene, Priestly was supposed to be back in his punk-rock clothes, but there were issues with his hair.