hapless
He plays a haplessly enthusiastic high school drama instructor.
He died in the Boer War after years spent haplessly seeking his fortune in the colonies.
Spitefulness pours haplessly out of his mouth as the others look on in appalled fascination.

SMART Vocabulary: related words and phrases

Feeling sad and unhappy
a long faceidiom
abjection
angsty
be cut upidiom
be down in the mouthidiom
be in a funkidiom
dismayed
displeased
dissatisfied
distraught
distressed
lonely
lonesome
lovelorn
lovesick
wistful
wistfully
woe
woe is meidiom
woebegone

You can also find related words, phrases, and synonyms in the topics:

Good luck and bad luck