loser

(sports) match, game

to lose

(intransitive) to lose; to be defeated / (transitive) to lower in price

(informal) to have "won" a match on a psychological or personal level despite losing to all appearances

oneself / first-person pronoun: I, me (often shows the speaker's lower position in a hierarchy than the addressee) / (Kansai) you

he / distal demonstrative, something far off removed from both speaker and listener: that / boyfriend

distal demonstrative, something far off removed from both speaker and listener: that, yon / particularly, male personal third person pronoun: he / by extension from he: boyfriend

he; boyfriend

(と〜) thinking that […] (with the next clause explaining that the truth is contrary to expectations)