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A Complete Breakdown of Red's Relationship History on The Blacklist

You know Red is a fun date.

By Jessica White

For all of the revenge and espionage that Red (James Spader) has orchestrated onThe Blacklist, he's actually a sweetheart. It's no wonder, then, that he's caught the attention of a few women throughout his life. Yes, Red has remained single throughout the majority of the series, but that doesn't mean he lacks a romantic history, nor the ability to have a fun fling with someone every now and then.

Below, take a look back at every woman who has ever landed on Reddington's romantic radar on The Blacklist.

Naomi Hyland

Before Red's criminal career, he was married to a woman named Naomi Hyland and had a daughter, Jennifer Reddington. Hyland is of the select few people in the world who know that Red is an imposter for the real Raymond Reddington, who died many years ago. Red sadly prioritized building his criminal empire higher than Naomi or his daughter and was eventually forced to flee from the authorities and abandon his family.

Years later, Red reunited with his daughter, who informs him that Naomi was eventually murdered by some of Red's enemies. Naomi is a tragic tale, but she was one of the most pivotal women in Red's life.

RELATED: We Officially Have a Date for The Blacklist's Final Episode

Madeline Pratt

One of the first people we learn has a romantic history with Red is Blacklister #73, Madeline Pratt, who we meet in Season 1 of The Blacklist. To the public, Pratt is a beloved political socialite, but behind closed doors, she leverages her political connections with powerful superiors to orchestrate multimillion-dollar heists. Put simply, Red's type.

However, Pratt's shady dealings were too much for even Red to stomach, so he broke it off. Years later, Pratt caused issues for Red and the Task Force. But just as they narrowed in on her arrest, Red allowed her to escape. Does that mercy mean there still might be something there?

Cassandra Bianchi

Considering the tragic events of the Hyland family, for the majority of The Blacklist's run, Red has kept his romantic explorations to a minimum. But that isn't to say he doesn't have a few love stories tucked in his back pocket. Case in point: Cassandra Bianchi (Joely Richardson), one of Red's former lovers introduced in Season 7 of The Blacklist.

Red describes the smooth-talking Cassandra as “elegant, charming, and ruthless," an apt description of the master thief who became the apple of Red's eye. After they reconnect, we learn that Cassandra and Red only called it quits after Red chose to pursue the Task Force over a serious relationship. But as soon as Cassandra and Red reunited later on, it was clear that the smoke of their former flame lingers.

Anne Foster

One of the most heart-wrenching love stories of The Blacklist occurs between Red and his Season 8 love interest, Anne Foster (Rhonda LaChanze Sapp). Anne and Red's almost-romance led fans to see Red in a vulnerable light. Red met Anne while enjoying a day in the park, later bumping into her again and asking her on a date.

Because this is The Blacklist, Red obviously missed the engagement but later visited Anne at her home in Kansas. Red's visit had devastating consequences; Red's chaotic conflict with a former foe resulted in Anne suffering a life-ending injury. Upon notification of her death, Red also tragically learns Anne was in love with him. Anne was yet another casualty of Red's criminal misdealings, but with a short but sweet time in Red's life, many would argue her love was the purest of all. 

Mierce Xiu

Mierce Xiu appears in a scene from The Blacklist.

At this point, we can all agree that Red's law-breaking lifestyle doesn't lend itself to a healthy romantic relationship. Another aspect of Red's personality that isn't exactly the most swoon-worthy is his drive for revenge, which was essentially his entire vibe for most of Season 9 of The Blacklist. Amid Red's revenge road tour, Red met Mierce Xiu (Karina Arroyave), his bodyguard's sister and a shaman healer. Mierce became fed up with Red's vengeful spirit, parting ways with him for good. 

Weecha Xiu

In Season 10 of The Blacklist, we see Red attempt to pursue a romantic relationship with his former bodyguard, Weecha Xiu (Diany Rodriguez). We know what you're thinking: Isn't that Mierce's sister? Yes. In Season 9, Red donned a bit of a polyamorous lifestyle, thinking of Mierce as the protector of his soul and Weecha as the protector of his body. We see Weecha and Red's connection heat up in Season 10, where he has told Weecha that he would like her to be his girlfriend, but she has dodged his advances. Fans are fascinated to see where the connection is heading as the curtain closes during The Blacklist's final season