Sometimes it's better to be weird than boring, sometimes vice versa.
Certainly if you are "desperately lonely", that sounds like a situation where you might want to take (at least) a few (modest) risks to make a few more personal connections, absolutely. Yeah, don't be terrified of being weird, or being seen as weird.
But I think if you want to make a connection, artificially-weird is not, i.m.h.o., your best strategy. And I think that's what's being suggested in TFA (perhaps jokingly). I'd consider aiming instead towards more honesty, and that means (a little) more vulnerability.
Now, if your honesty reveals that in some particular ways you are a weird person (which would, in general, be a good sign of being potentially interesting and worth connecting with), well, that might work against you in some instances. Or it might work for you in some instances. If it's important that you gain the trust of this particular stranger right now (perhaps a cop who is considering arresting you), maybe you wanna try to downplay the weirdness in this particular interaction, to avoid ugly outlier reactions.
But in the making-friends department (and in the finding-lovers department, if you're not Wilt Chamberlain), the goal is not to be everything to everybody. The goal is to winnow the chaff of the public-at-large to find people whom you like, and who like you. So take some chances, put a few people off. If you get rejected (or you yourself reject) 99% of the population... well, just try making friends with 1000 people (say one a day for 3 years) and you'll have no shortage of friends. Being "normal" is a liability! Your weirdness may bore or repel most people... but someone eventually will find your weirdness interesting or attractive.
So, if you need to go with non sequiturs to break a fear of doing anything interesting at all, well, that's a start. But I think it would be better to seek topics that might be genuinely interesting to both parties (unlike, say, conspiracy theories about Pearl Harbour, which probably aren't genuinely interesting to either party, even if they're more interesting than super-boring small talk).
For example, a strategy I respect very much is to ask people about themselves or their life (hopefully in a way that flows fluidly from a sentence or two of small talk), and when their story includes something that surprises or interests you, ask questions about that interesting or improbable aspect. (I wonder if Alton is reading this.)
My apologies if any of the foregoing sounds patronizing or otherwise insulting.
Good luck with the loneliness, you have my sympathy.