I think context is key: who, what, when, where, why. If I'm picking up my daughter from school, striking up a conversation with someone (i.e. another parent) w

I think context is key: who, what, when, where, why. If I'm picking up my daughter from school, striking up a conversation with someone (i.e. another parent) would be totally different than making chit chat with someone at the bar/club. Often, the thing that previously held me back from talking with someone was fear of rejection, something I really struggled with in my early 20s and found that as I've gotten older (mid 30s now), I'm much more comfortable under my own skin and find it easier to approach strangers. I don't think the fear will ever disappear but, does get easier (in my case) with age.