Hi Captain Awkward,
The background to this story is I moved away from the city I grew up to go to graduate school on the other coast. While I have been in the area a while I am currently living with roommates I did not know prior to living with them. This is fine and for the most part they are very nice. However one of my roommates, lets call her Reba, is very nosy.
Specifically, Reba constantly asks incredibly personal questions and constantly offers to hear my personal problems. This really came to a head a few weeks ago when I finally broke up with my boyfriend of 4 years. For the most part the break up was amicable, it really was just we are at a point in our lives where we want different things; I am trying to finish my Ph.D. and then hopefully have adventures as a post doc while he is trying to buy and house and settle down. Anyways I decided not to tell Reba (and the other roommate Mike by proxy) because I did not want to talk about it and my personal life with Reba. But a few days after it happened Reba mentioned that she had over heard me talking on the phone about breaking up with my boyfriend. And then talked about how she is really good at listening, and will be totally fine with hearing all of my problems about the break up etc. etc.