I don't entirely regret it but I did buy something without looking into what I was actually buying today. I wanted to get the Hotline Miami 2 OST and on Steam I saw it was 15 bucks, same price as the base game, but then I saw there was a "Deluxe" edition of HM2, and for 5 bucks I could upgrade my base copy of the game. I assumed that since this deluxe thingy required the base game, the deluxe one was the OST and would save me 10 bucks. It isn't, in fact, I have no idea what I bought, I checked my file folder and there is a "remix" folder which I think is new, and contains 6 remixes of tracks from the game, but it wasn't what I was looking for. Still don't exactly regret it because I want to support the game. Still wish I had googled it though before I spent the money.
I double checked my steam library and there aren't any games that stuck out to me as being major regrets, because the games I have that I don't play are ones I got on steam sales for dirt cheap and are games I at least believe I will get to eventually.
That said, Mass Effect 3 is the one game I truly regret. I regret getting it so much, I actually regret the first two games, which I enjoyed, because due to my distaste for ME3's ending, I will never be able to play the first two again. 60 bucks preorder for a game I didn't like while I spent 10 bucks for ME1 and ME2 and I really enjoyed them.