I think a lot of the relative ease depends on whether or not you’re okay with rejection, i.e. initiating contact when you’re not sure if it will be received well. I was terrified of this in my teens and early 20’s and probably missed out on a lot of great opportunities because I didn’t always have the balls to ask her out.
The women I’ve asked out on dates since coming back on the market were the ones where it WAS easy (no, not THAT kind of easy). Easy meaning we connected well initially over at least a few things, some attraction was there and the conversation wasn’t too awkward. The gal I was with last night I’ve known for a few years through mutual social circles, which also makes things easier because there’s a certain level of vetting that’s already taken place for both of us.
From a social awkwardness perspective, I’ve always tended to do well after the ice is broken and some rapport is established, i.e. she’s already agreed to a date. I can usually keep a conversation going once it’s sparked (not that hard, just ask good questions) and I’ve learned to save my more tasteless jokes for future dates rather than blurt them out. I’m also a gentleman and know how to conduct myself on a date.
Now, getting the right date and making it all work out long term, that’s a trick I haven’t mastered. 9 years is the furthest I got before a reset button had to be pressed.