Yes it should be awkward, but at least in my experience in the past this was expected to happen. And the person on the other side of the awkwardness would mostly be receptive from the tentative approach.

I feel like nowadays, because it is so much easier (but fake) online, most people simply gave up all tentative of approaching//being approached in real life.

I mean meeting people in real life still happens, but it is getting more and more rare//isolated and awkward unfortunately. I guess we live in a society where everything needs to have a well defined flow and be well codified.