Way back in the day when Bitcoin first came about, I once idly contemplated spending some time and money on it just because it was a very cool technology. At the time it was a bit of a hassle because you had to mine your own.
Then I was especially tempted years later after running into the MtGox booth at CES, and seeing how convenient it had become. I remember asking a guy at the booth if Satoshi was really still anonymous or if any insiders knew about him, and he said "no" but was bit surprised I knew about Satoshi. I guess Bitcoin was still quite niche then even amongst a technical crowd.
I considered buying a few bucks worth of bitcoin then for lulz, but I thought that money was better spent on beer lol.
I've never really regretted spending that money on beer rather than bitcoin, because I knew that even if I did, it would 100% have been on MtGox and I would have lost it in the hack anyway, which would have been even more bitterly frustrating.
A few of pints of beer >> years of regret.