Poor Red just isn't going to be allowed to find happiness.
We finally got to discover who Anne was on The Blacklist Season 8 Episode 13.
And surprise! She was just as she seemed to be, an innocent tourist who Raymond happened to run into at a New York City park.
This being The Blacklist, the consensus among viewers was that she was a plant by somebody (Liz, Townsend, someone else from Reddington's past) who was out to seduce him.
And it appeared he had done the right thing back on The Blacklist Season 8 Episode 8 when he stood her up for "North by Northwest."
All he would have to do then with deal with regret and he's far too busy for that to linger.
Red really should have known better than to pursue Anne any further. After all, it's dangerous for any civilian to be around Red, as this episode proved with gusto.
It also had a real what-if feel to it. Like what if Raymond just walked away from it all to settle into Midwest, small-town life?
Everyone involved seemed to think Rayanne was just a bad idea for many reasons.
Dembe didn't begrudge Reddington having someone in his life. He rightfully didn't like the idea of Red out there unprotected even in the middle of nowhere.
That's because, no matter how well Raymond covers his tracks, trouble follows him.
Anne's friends Bran and Lois just didn't trust the secretive man from New York who had insinuated his way into Anne's life.
It was hilarious that, with all the complicated things that Reddington had dealt with in his long life, bridge gave him fits.
Still, Red managed to fit into Anne's world, in short bursts anyway. He just couldn't leave all that he'd built behind, no matter how distracted he was by Anne. He was actually able to relax enough to fall asleep during a film.
Fortunately, Raymond took Dembe's words about keeping his eyes open to heart. It's not paranoia when people are out to get you.
Seeing the same van at two different places he was triggered Reddington's spidey sense and he sadly knew his small-town life was coming to a close.
Should Red have been more persistent about telling Anne who he really was so she might be better prepared when trouble found them?
He did inform her he was a fugitive when first they met but she thought he was joking. And now that they were settling into being a couple, she really didn't want to know the truth. She was enjoying the fairy tale, a second chance at love during her later years.
As was Reddington. But as many people as he has tracked down through the decades, Raymond had to know his time with Anne was limited. Of course, Townsend located him and came after him and now Anne was in danger as a result.
He tried to get Townsend to leave Anne out of their battle. But since Townsend blamed Red for the death of his family, that was never going to happen.
Exactly what Dembe was worried about had come true: Raymond by himself with no protection. Not that he was helpless, as Townsend's thugs soon found out, falling one by one.
But he was severely outnumbered so he did the only logical thing he could: turn himself in to the police to gain law-enforcement backup.
Only the yokel cops were ill-equipped to be sandwiched between two international criminal masterminds. Dealing with drunk and disorderlies and speeders takes quite a different skill set.
That's why most of them ended up dead on the floor. Red had to keep telling them to keep their heads down and stay away from the windows. Anne performed better under fire than most of them.
At least they eventually did the math, figured out how badly outnumbered they were and called for backup. It was too late then to do much good but it was something.
It was great to see Kathryn Erbe (Law & Order: Criminal Intent) surface as a quite different kind of cop, the small-town variety. She was the smartest one of the bunch so it was little wonder she survived.
Realizing what he was dealing with for troops, Reddington did the only thing he could, locking the three of them inside the holding cell, which bought them just enough time for the backup to arrive and save them.
What was surprising was how Anne still stood up for Red even after all the chaos he had brought into her life.
She stood up to Lois so that Lois would let Raymond escape. It was only fair since his first aid had likely saved Lois's leg.
Then she coolly lied to the FBI agent and drove home with Reddington in her trunk.
They both realized that, no matter how they felt about each other, they couldn't be safe until Red got out from under Townsend's pursuit.
He should have kept driving. Then he would never have found Liz holding Anne at gunpoint.
This will truly show how far gone Liz is. Is she really to harm an innocent woman who had the bad luck to fall in love with Red?
To review Red and Anne's relationship, watch The Blacklist online.
Shouldn't Raymond have known better than to start something with a civilian?
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Dale McGarrigle is a staff writer for TV Fanatic. Follow him on Twitter.