I’d like to begin by saying that I have a good understanding of where I stand in terms of my own attractiveness, intelligence and social stature. My previous dating experience has also been with men in the same league. However I do come across men every now and then who wouldn’t be considered attractive, intelligent or masculine by any measure, yet they seem to have the confidence to approach me and ask me out.

I want to know this sub’s view on how you handle such situations and I’d also like to understand how some men have the confidence to approach women out of their league.