- I turned 27 last month and I've never dated/had a girlfriend/ or even asked a girl out. Sometimes I feel like I missed out on dating. People have always told me "itll happen eventually" since high school and for 10 years now nothing is new in my life. Nothing random or serendipitous. I've been trying to focus on myself for 7 years, doing hobbies work etc. But nothing random has happened. No one has come along or anything. how do people meet in the most random ways possible? I'm introverted and usually a quiet person and sometimes when I do talk to girls I dont really do anything other than give them their space or worry that I'm making them uncomfortable. I used to sit in the corner at parties smiling and watching, usually waiting for something unexpected to happen. That was my interpretation of "letting things happen naturally". So if I do meet a girl, how do I let things happen naturally? do I wait for signals? Do I stay quiet? Do I not ask the girl out? I'm just waiting around for something random to happen. what is "letting things happen" mean? Please help? Thanks?