I'm not sure what's regrettable about this information.

In the next scene where the date takes place, they embrace their old school cool, knock it out of the park, and have a blast. It genuinely romanticizes being this old and made me look up to being this old when I watched as a kid.

All this meme is telling me is, "Congrats, you made it, now go find people in your cohort and live it up with them in ways that mean things to you, even if the kids think you're cringe," and that's wonderful.