I do try not to have too many regrets, though it is surely impossible to go through life without having any. I am fortunate that I do have enough time and usually enough funds to see all the theatre that interests me in Toronto (though I did skip Burn This as the tickets just seemed too high to me). That might not be the case if I was still in Chicago (not having enough time) or New York (where even the off-Broadway ticket prices have become ridiculous). Concerts are a bit of a different story, as they have gone up (in my view at least) much beyond the rate of inflation and the scalperbots have gotten so good that it may be very difficult to actually get tickets at all, and then you have to decide about buying them secondhand (in addition to costing more the odds are reasonably high that you'll get scammed). So I do a lot more picking and choosing.
Anyway, all through high school I didn't live anywhere near a major metro area and didn't see any rock concerts at all. I was probably taken to a few classical and jazz concerts, but nothing that really sticks out in memory. (I do remember one boy in band managed to convince his older cousin or someone to take him to a U2 concert,* but that was quite the exception.) In university, I was close enough to Detroit (and it hadn't quite fallen on hard times to the degree it has today), so for major acts, we would go, though I still don't think I went to more than 6 or so concerts in Detroit (David Bowie, The Who, The Grateful Dead, Bruce Hornsby, 10,000 Maniacs and maybe one or two more). I liked music, but I just wasn't that much of a concert-goer. Maybe it would have been different had I grown up in a big city where all the big acts were passing through.
I won't go too much into all the concerts I didn't go to,** but just focus on a few where I had considered, but for one reason or another, decided not to, and then (too late!) had second thoughts.
Probably #1 is when Paul Simon played a small venue on Belmont, not that far from where I lived in Chicago. Definitely still kicking myself about that one.
Right around that time, I skipped the chance to see Toad the Wet Sprocket playing in the Lincoln Park Zoo. I think for both of these, I mostly didn't go because I was trying to adjust to having two small children and just wasn't sleeping all that well.
I think there was a Bauhaus reunion tour that passed through Chicago, and maybe I should have gone. I heard it was actually pretty good.
On a recent visit to Chicago, I could have see Jackson Browne playing an event. He was only backed by one slide guitar player, and I guess I just thought he would sound better with a full band. While I probably still should have gone, this won't be something I take to my grave regretting...
Similarly, I've been pretty interested in trying to catch Bruce Cockburn, but the last few times he's come through Toronto, it's been a solo show. I'd really prefer to see him playing with a band.
I wasn't a huge, huge Leonard Cohen fan, but I still should have tried to catch his final tour. Ah well.
Also, Prince kept hinting he was going to have a secret show in Toronto, and then he actually did a show (I believe he played piano only) and then less than a month later he passed away. For sure, that's one I would have liked to have attended.
More recently, my wife asked if I wanted to see Hall & Oates in Toronto. We saw them in Chicago, and they were quite good, but I wasn't sure I really needed to go again. What I didn't realize was that they were sharing the bill with Tears for Fears. Had I clued into that, I'm sure we would have gone.
I didn't like either of the venues that Collective Soul chose when they came to Toronto (and they came twice in 2016!). They aren't coming in 2017, but they have a new album coming out and perhaps they will come back in 2018 (and I'll make more of an effort the next time around).
I'm sure there are dozens if not hundreds of concerts that I would have liked to see, but these are the ones that kind of stuck with me. That's probably not so bad (not so many regrets) in the grand scheme of things.
* I still haven't found any U2 tickets that were any good on any of
their later tours, so I may never end up seeing them. That's
** I don't really want to add jazz to the mix, though I was supposed to see David Fathead Newman in Chicago (taking my father-in-law) but he got sick and actually died just a few weeks after the cancelled concert. (And I probably should have gone to seen Elvin Jones at the Chicago Jazz Fest when it was pretty clear it was one of his last tours.) In terms of pure regrets, looking at the walls of the Jazz Showcase and just trying to imagine how amazing it would have been living in Chicago in the 1960s-80s (as an adult) makes me wish I had been a generation older. Life would have been a lot easier in a lot of ways (assuming I avoided the draft...), though on the whole I didn't mind growing up in the 80s.