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Black Widow

Wade tells Black Widow he likes her.

KISS

Wade and Yelena "kiss".

The Black Widow (Yelena Belova) was the leader of the Thunderbolts. Norman Osborn used her and the rest of the Thunderbolts to kill Deadpool.

Plane

Wade sends a message through the sky.

However, during the course of the event, Wade and Yelene fell in love with each other. However, despite a kiss, the romance never truly flourished.

But, after the Thunderbolts believed Wade to have died, Yelena secretly sewed Wade's head back on his decapitated body and the healing factor did the rest, so some feelings were there.

In later stories, unrelated to Deadpool, it was revealed that the Black Widow Wade had feelings for was in fact Natasha Romanova in disguise, the original Black Widow, working for Nick Fury, turns out most of the T-Bolts felt the same way too, and Headsman, Ghost, and Paladin all turned against the other T-Bolts to save her and Songbird.

Unfortunately, Black Widow is killed by a Hydra influenced Captain America, punching her neck with his shard shield while she sacrificed her life saving the other Spider-Man/Miles Morales from him.

Of note, it is significant to point out that Ryan Reynolds who played Deadpool in the Marvel Movie Universe and Scarlett Johansson who played Black Widow in the Marvel Movie Universe were married in real life from 2007 - 2011.

Widow fan

Wade's fantasy about Yelena.


Wade and Black Widow met in the following comics:


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