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Genre I'd say it's a romantic comedy, not quite sure

Time Period and Origin I guess, it was made between 1995 and 2000; extended range of 1990-2002, but I'm certain it isn't earlier than 1980 or later than 2006. Fairly sure it's an american movie.

Setting A modern, big city setting (I want to say New York or London, but not sure)

Characters I remember the main characters quite well. The protagonist is a geek, who just came to the city for a job or school, he sticks out like a sore thumb, because he wears a warm woolen hat all the time. Similar to this:

enter image description here

The female lead is a red-haired woman, maybe early twenties or late teens, who has a goth-vibe about her.

Plot The plot revolves around the female lead helping the protaganist get his footing in the city, I'm pretty sure a romance blossoms between the two, but can't remember anything of the latter half of the movie.

Extra info The one thing I clearly remember is a scene, where the female lead asks the protagonist, why he is wearing such a silly hat all the time and he responds, it's because the body loses most of its heat through the head, which is why he wants to keep it warm.

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up vote 17 down vote accepted

This is Loser, a 2000 film starring Jason Biggs (who played Paul) and Mena Suvari (who play Dora) set in New York City:

enter image description here

From the wiki description:

It is about a small-town teenager who is accepted into New York University and must cope with the pressures of college life and the big city.

From the script:

Dora: So how come you always wear that hat?
Paul: 'Cause something like 90% of your body heat escapes through your head.

A picture of the characters:

enter image description here

And finally a picture of Paul, portrayed by Jason Biggs:

enter image description here

The hat picture and reference to losing heat through the head gave it away instantly.

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You beat me to it! Here's a link to the trailer – djmadscribbler Feb 3 at 20:37
This is indeed it. Thank you for your very thorough answer. – Dulkan Feb 3 at 20:50

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