Cold approaching someone to ask them out - especially if they hadn't yet AT LEAST exchanged smiles - seems to be the sign of a deluded/misguided person. And even moreso with such an enormous - and generally creepy - age difference.

More prudent and effective would be to approach a group, chat with them, and build a rapport. Then see where things go.

Even more prudent would be to not be so utterly pathetic and desperate, and instead just focus on doing things that bring you fulfillment. And then meet people who also do those things, some of who you will just click with. And perhaps even romantically. There's no "approach anxiety" that way because there's no "approach" at all! Just live an authentic, contented life - that's what's actually attractive to people.

The problem is that most people do not live an authentic life. But there's nothing stopping them from starting today and endless options for it. But keep "dating" out of your mind - just go and connect with people, develop interests, skills, self confidence etc