I feel like i dont know how to start conversations that could lead to dates. I (35M) am interested in this girl i used to work (36F) with and would like to ask her out. But we have not talked in quite a while. When we worked together we got along well and joked around a lot. Now she is posting stuff on facebook about being single and basically posting about what she wants out of a guy, you know typical attention seeking type of stuff. How to i start a conversation with her (online) without seeming desperate or boring?
With what she has been posting its obvious she is trying to date again and i would like it to be me. Thanks in advance for any help. Typically when i am trying to talk to someone i am interested in a quickly start getting short responses which makes me think they arent interested.