James T. Kirk/Relationships/Romances/2280s/Antonia

Kirk fell in love with Antonia after his first retirement from Starfleet in 2281. The two lived together for some time before Kirk decided to rejoin Starfleet. Later in life, he regretted not having proposed to her. He would later be reunited with a life like illusion of Antonia during his 75 years in the Nexus, which was, from a chronological standpoint, his longest-lasting romance. ()