Cynoptimism 

Cynoptimism; (sin-op-ti-mism) The personality trait of one who is both cynical in their opinions while maintaining a measurable amount of an optimistic outlook on life in general. May be a more noticeable characteristic during a humorous telling of an anocdote that is dark in nature, yet light in delivery. See also "cynoptimist."

"You've made my cynoptimism into full-blown pessimism."
"I liked him more when he was a cynoptimist rather than a full blown cynic."

Cynoptimism by playerD666 September 21, 2016

cynoptimist 

A pessimist who is driven by hope. A paradoxical balance between being a skeptic and a utopian idealist. Wishfully wary. A guarded viewpoint with no tangible protection. Reckless yet cautious or reckless prudence. Circumspect with abandon.

He does not believe in God, but he hopes there is one, making him a cynoptimist about faith in a higher power.

cynoptimist by Ranger Wordsmith February 7, 2015

condoptimism 

When one is preparing to go out for the evening, without any particular reason to expect ensuing romantic congress, and deciding whether or not to bring prophylactics, and decides, "you know what? Yeah. Fuck, you never know, right?" and packs a condom or two. See also: unbridled condoptimism, packing three or more condoms. See also: optimisticondom, a term for such condom itself.

In a fit of condoptimism, I put a Trojan in my coat pocket.

condoptimism by ericardo March 31, 2008