"If you can find the line between sympathetic and creepy, you have reached a very funny area"

In this quote, Jason Segel is suggesting that there is a fine line in between being considerate and being scary. He believes that if one can discover this line, they have reached an uproarious location. This could imply that when somebody is able to balance being understanding and caring with being somewhat upsetting or unusual, it can result in a funny situation. Segel may be suggesting that being too sympathetic can come across as insincere or overbearing, while being too creepy can be off-putting. Nevertheless, discovering the right balance in between the 2 can develop a comical impact. In general, Segel is highlighting the significance of finding a happy medium in order to attain humor.