I haven't dated in about 2 years, and recently began to do so again. Because of this (and my spotty confidence), friends have suggested I date women who aren't all that attractive so I can get my sealegs back. So, someone that's comfortably between a 5 and a 6 - not someone I would be ashamed to be seen with, but someone I might not be dating long term in my journey to better myself.
How do I go about this carefully, ESPECIALLY if it's in a social circle where I could end up getting a reputation? (I dated a woman from this same circle about two years ago just to give her a shot, and broke up with her about three weeks later in a very sloppy fashion. She's never quite gotten over it.)
How do I go about this carefully, ESPECIALLY if it's in a social circle where I could end up getting a reputation? (I dated a woman from this same circle about two years ago just to give her a shot, and broke up with her about three weeks later in a very sloppy fashion. She's never quite gotten over it.)