I don't really enjoy doing this anymore. I think it is because when I first started doing it a couple of years ago I was oblivious to signals and signs and would ask out random women w/o actually thinking about whether they were giving off positive signs or not. Plus I have had some bad experiences in my past with asking women out. I guess all the obliviousness on my part caused me to be embarassed to the point where I don't want to do it. So do you enjoy it? If so, what is your outlook that lets you enjoy it? I am wanting to get back into this but to do it with dignity and a sense of fun, and I'm not really sure how to do that. Here is a list of reasons I don't really enjoy it, off the top of my head -worry that I'll get made fun of (which has happened for various reasons). I want to become more assertive when some guy who sees me doing this makes a snide, insulting remark and I want to learn how to avoid women who are condescending as much as possible. -worry that if I do it that the womans relationships with me will change (she'll become standoffish and avoid me, or I'll avoid her if I ask her out) Does anyone have any ideas on what to do to overcome these things, or failing that to just enjoy talking to women and not taking it beyond that? What I noticed was that if I just stopped asking women out and instead just talked to them and flirted with them that I was more comfortable. So perhaps I'll just have to reserve myself to doing that.