Back when eBay was young, I was drinking A LOT with friends while bidding on a used folding kayak.
I got angry with a competing bidder and wound up paying a lot more than I would have sober. (I later learned about sniping services. I rarely buy things in online auctions anymore, but that may have been the last time I was foolish enough to watch the end of an auction and try to outbid someone who was likely a bot.)
The kayak still cost much less than a new one, and I used it for about a decade before selling it to someone else.
Paddling around Cape Cod almost always beat any gym workout I can remember.
A healthy savings account. Not exactly a purchase... but drunk me often writes notes in my phone to share her drunken insights.
One night I drafted a 2-year savings plan and transferred a sensible amount of money into my savings account. One of my drunken "ideas" was to start receiving my tips in as much change as possible (I was a waitress and we pooled tips) because I was less compelled to immediately spend change. Then I would roll up the coins every two weeks and deposit them into my savings account.
I actually ended up saving $400+ just in change within a year. And it turns out I find rolling up coins very soothing.
10/10 would drink and manage finances again.
I was losing my job because of some merger bullshit, but they announced the layoffs two months in advance so I could plan ahead.
I was drunk as hell, looking at job sites and getting depressed and said: "Fuck it! I'm going to Hong Kong for two weeks and I'll deal with this shit when I get back!" (Why HK? I dunno, I was drunk.)
I went to cancel my ticket the next day (within the 24 hour window you get), but I researched the dates I'd be there and it was the same week as the Hong Kong 7s rugby tournament so I kept the ticket.
Ended up being one of the best two weeks of my life. Hiking, swimming, exploring the city, gambling in Macau. I went on dates with girls from Australia, Canada, England, China, and Hong Kong; all through the miracle of Tinder. I got a free 3-day ticket to the Hong Kong 7s from a girl who got them free from her work. I ate incredible food. I visited the Fuji Building and got the courage to ring a doorbell. Then I promptly exited the building because I felt so creepy. I got drunk and lost a bunch of money at the horse track. I got to ride on a free party trolley with beer, sponsored by the HK tourism board. And I made a couple life long friends. I love Hong Kong.
Still looking for a good job though.
A subscription to early readers books, like Dr. Seuss and whatnot, for my one year old. She loves books and now I don't have to read the same 6 books over and over aging. Plus, it's like reliving my childhood.
An Improv Level 1 class. I still play in shows regularly.
H/T: Ask Reddit