Most embarassing: probably when I was 14 and my crush at the time rejected me through MSN (people under 20 will have no idea what I'm talking about xD). And the funny thing is that I'll actually be seeing her in a few days at a friend's birthday. Haven't seen her in at least 5 years and I learned she's now a model, which I guess is evidence of my good taste xD
Best day: Tough to say... I'll just go with the whole year of 2014, which is definitely the best year of my life so far (though hopefully not anywhere near the best going forward). Not for anything specific, just the general vibe of the time and a lot of good things and encounters that happened to me around that time. Also, contrary to most of my adolescence years, I wasn't battling depression and anxiety.