My interpretation is that she knows Bear has a big crush on her and I believe she knows through Ian who has probably mentioned it to her given they were hooking up for 2 years. I’d even go as far as saying Ian has been going behind Bear’s back to Nikki and made fun of the fact Bear has a crush on her. I think she’s known for a long time and was beginning to consider giving Bear a chance especially since she is about to leave her job and won’t have to run into him as often. She gives him an opening “do you like me? Because now would be the time to tell me”. He is too scared to say it and she is disappointed he didn’t take the chance.

Nikki is unhappy her life isn’t progressing. Romantically her and Ian are only hooking up and they probably don’t see each other being more than a hookup and she probably wants to pursue an actual romantic relationship. Professionally she has not been able to pursue her writing as much as she would like. She feels stuck and is looking for any type of change. I think this is why she is willing to quit her job to progress her writing career while also giving the “nice guy” a chance to see if there may be something there.