Firstly, I kinda hate the phrase “no regrets”, not necessarily for its sentiment, but more for how it has been co-opted to be a slighter tamer version of the much-besmirched “you only live once”. If I was into the whole ironic tattoo thing, getting it misspelled somewhere on my body would have some non-zero amount of appeal. Honestly, it might be as bad as “bad decisions make good stories” and that phrase has been panned hard by my readership recently.
I agree that at first glance, it can seem like a useful vector through which to make decisions - take which ever path you think is likely to leave you with fewest regrets. However, in practice, I’m not so sure I agree, largely because I’m not sure regret is an especially useful thing to feel more generally. In any situation, I think we make the best decision possible using all the information available to us. In retrospect, once we have new information, of course that might make it plain that it was a flawed decision, but is it actually useful to feel regret that we made what we believed to be the best decision at the time, which turned out to be wrong - essentially an honest mistake? I don’t really know - maybe if our retroactively bad decisions are borne of fear, laziness or apathy then yes, it is worthwhile feeling regret over those. Maybe when choosing which fork in the road to take and considering potential regret, what we are actually doing is examining our own motivations for the decisions, and asking ourself if it is pure of heart or a child of cowardice.
I don’t know. But yes, you absolutely should regret not ordering dessert, there’s clearly something wrong with you.