James T. Kirk/Relationships/Romances

Often described as a ladies' man, Kirk was notably successful in attracting women, and enthusiastic in their pursuit, yet notoriously unsuccessful in establishing any lasting relationships with women – a fact his brother Sam tended to warn women about. () By design or coincidence, his most significant affairs were with women fundamentally incompatible with his life in Starfleet. In weighing the balance of starship versus a settled home life, the gross tonnage of the Enterprise usually tipped the scale. ()
As Kirk became more and more well-known, these exploits became the stuff of legend; when Jadzia Dax, upon seeing Kirk while aboard the Enterprise during the Defiant crew's trip over a hundred years into their past, mentioned how much more handsome "he" was in person, Captain Sisko responded that Kirk had "quite the reputation" in terms of his dealing with women – though Dax then admitted that the "he" to whom she had referred was actually Spock. () 
While attending the Academy, Kirk was romantically involved with at least two women.
<tabber>
|-| 2250s=
|-| 2260s=
|-| 2280s=
|-| 2290s=
</tabber>