Top 10 Times the Hero Slept with the Enemy

“300: Rise of an Empire” (2014)

In this sequel to “300,” what starts as a negotiation between two opposing military leaders ends in…well, something a little more than politics. Athenian general Themistocles is summoned to Persian Queen Artemisia's warship for a quote-unquote “meeting.” After some epic flirtation, Artemisia seduces Themistocles and attempts to convince him to join her side and become her lieutenant. While he does, er, “seize her glory,” Themistocles rejects Artimesia’s offer to team up - which the notorious female warrior does not appreciate. Following their fling, the scorned Artemisia noticeably amps up her fighting game. Guess we don’t all take rejection well.

“Marvel's Agents of S.H.I.E.L.D” (2013-20)

Grant Ward really got around - at least until he was outed as a double agent. Ward entertains not one but two flings with S.H.I.E.L.D agents while serving as a false member of the heroic team, and ends up betraying and deceiving both women when they discover he’s been working for the criminal organization H.Y.D.R.A. Early in Season 1, he begins a secret affair with veteran agent Melinda May. But their spark dies down when he falls for - or, at least, appears to fall for - a hacker named Skye, whom he is assigned to train. When Ward’s true loyalty is revealed, neither of his flames are too happy.

“Dexter” (2006-2013)

Don’t you hate it when you end up falling for the very murderer you’ve been chasing all season? In Lieutenant Debra Morgan’s case, that’s exactly what happens at the end of Season 1. The titular anti-hero’s adoptive sister enters a relationship with friendly prosthetist Rudy Cooper. The two have what seems to be a normal courtship, and Debra is obviously smitten. However, we soon learn that Rudy is the Ice Truck Killer, who is being investigated for killing and mutilating multiple women. It turns out that Debra is just a pawn in his plan to get close to, and ultimately team up with, his long-lost brother Dexter. The ordeal leaves poor Debra traumatized.

“Arrow” (2012-20)

Season 2 sees Green Arrow himself fall prey to yet another enemy in an ally’s clothing. Isabel Rochev, an executive at Queen Consolidated, cozies up to Oliver Queen (aka Arrow) while in Russia. As events unfold, we learn that Isabel has been in the pocket of evil Slade Wilson the whole time and had been preparing his Deathstroke army behind Oliver’s back. Isabel wants revenge on the Queen family after Oliver’s father, Robert, abandoned her years before. While this is one of those flings on the list that doesn’t go on much longer than a single night, we can’t help but feel bad for Oliver for the predicament he finds himself in.

“Game of Thrones” (2011-19)

So this one gets a little complicated, as “Game of Thrones” loves to keep audiences trying to figure out who the “hero” and “villain” are. But Daenerys’s actions towards the end of the series paint her quite clearly as “bad news.” By Season 7, the Mother of Dragons and King of the North have formed not only a sturdy alliance, but a romantic bond as well. (Unbeknownst to them, they’re also related, but that’s beside the point.) Jon and Dany’s royal romance crumbles around the time she destroys King’s Landing, and he comes to recognize her as the tyrant she has turned into. As a result, he’s forced to make an agonizing decision in the finale.

“Killing Eve” (2018-22)

If there’s a fine line between “sworn enemy” and “passionate lover,” the relationship between Eve Polastri and her arch-nemesis Villanelle is pretty much the embodiment of that line. The British series follows MI5 agent Eve in her hunt for infamous assassin Villanelle. Along the way, Eve and Villanelle develop a mutual affinity for one another that may be called love, obsession, or a dangerous mixture of both. Over the show’s four seasons, we see their dynamic evolve from “cat-and-mouse” to a tight, if twisted, bond. At least things appear to end well for the badass couple.

“Indiana Jones” Franchise

“Indiana Jones” fans were genuinely surprised when our hero’s rendezvous with Dr. Elsa Schneider panned out the way it did. In the third film, Schneider, a beautiful Austrian historian, teams up with Indy on his search for the Holy Grail. One romantic day in Venice, the two of them go for a nice little “roll in ze hay.” Not long afterward, though, Schneider reveals herself as a Nazi sympathizer who has just been using Indy - and his father - to acquire the Grail for Hitler. This bitter revelation certainly makes things awkward whenever they have to interact throughout the rest of the film. And it doesn’t help that Schneider is implied to have had a run-in with Indy’s dad, as well.

“Buffy the Vampire Slayer” (1997-2003)

What begins as a bitter rivalry between vampire and Slayer becomes one of the most controversial romances in television history. When Buffy first meets Spike in Season 2, he’s a feared vampire who’s already defeated two Slayers over the course of his tortured eternal life. After a bizarre turn of events, Buffy and Spike become allies and, a little while later, a couple. As the seasons develop, viewers observe every step of the toxic “dance” that is their relationship. There may be a lot of passion between Buffy and Spike, but fans often describe their union as “unhealthy,” and it’s easy to see why.

“The Dark Knight Rises” (2012)
The “Batman” franchise enjoys having its heroes fraternize with the enemy, and one of the most notable instances occurs in “The Dark Knight Rises.” The 2012 blockbuster finds Talia Al Ghul - daughter of Ra's al Ghul - posing as the CEO of Wayne Enterprises. She befriends and earns the trust of the brooding Bruce Wayne and eventually becomes his lover. Whereas other incarnations of Talia have been more sympathetic, in this film she’s pretty underhanded, very clearly using Wayne in her plot to avenge her dead father and destroy Gotham. Tough break, Bruce, but at least you’ve still got Selina.

“Casino Royale” (2006)

No matter the movie he’s in or the actor portraying him, 007 certainly seems to have a type: the bad girl. From Pussy Galore to Elektra King and beyond, Bond just goes mad for these off-limits ladies. But the one that takes the cake is Vesper Lynd from “Casino Royale.” In this installment - which chronologically comes before all the other “Bond” films - the sultry, seductive Lynd forms what seems to be an honest connection with Daniel Craig’s Bond as they attempt to combat a terrorist organization. Unfortunately for Bond, though, Lynd is eventually disclosed to be a double agent and ends up breaking his heart. All the same, one might argue that Lynd brings out a softer side of 007 that we never see again.