Red makes a personal connection, with heartbreaking results.
Of course, this is far from the first timeThe Blacklisthas dipped its toes into romantic disappointment.
We’ve never really seen him get romantic with anyone, let alone get hurt.

Will Hart/NBC
Personal relationships make Reddington and the people he cares about vulnerable to those who would seek to hurt him.
Let’s see how the greater good is being served in this episode.
OGDEN GREELEY, NO.
40
The first thing you might notice about this Blacklister is: That’s a high number!
Ogden Greeley is a defense contractor for the National Reconnaissance Office who disappeared five days ago.
And he disappeared five days ago.
Oh, great a treasonous terrorist masquerading as a patriot.
This guy ain’t coming back to family life anytime soon.
So Cooper says they only have one option: the federal kill list.
Because the buyer is Raymond Reddington.
And speaking of adorable…
Anne.
Oh, lovely Anne!
They share a chicken salad sandwich, and you guys, it is all just charming as hell.
And when he hangs up Anne is there.
She’s canceled her car in lieu of getting Red to help her find a souvenir for her sister.
At least I know I fell in love with the idea of Raymond and Anne falling in love.
But eventually Dembe tells Red it’s time to fly to Mongolia.
He says he’ll meet her outside the theater with two tickets…
But on the flight back from Mongolia, Dembe douses Reddington with some sobering reality.
“I understand what she means to you, what she represents,” Dembe says.
But Reddington is sitting in a car across the street, and he knows that she did.
A FEW LOOSE ENDS
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