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‘Arrow’: When did Oliver Queen fall in love with Felicity Smoak?

The season 7 finale of Arrow delivered a lot of GLORIOUS Olicity content for us to chew on, dissect, and discuss. But the no brainer hot topic is the absolute tear-jerker that was Oliver and Felicity’s goodbye.

Everything about it was beautiful, raw, powerful, and magical. Us Olicity fans can talk about it all day, but specifically, we NEED to talk about one line in particular:

“My only regret is not telling you I loved you sooner.” -Oliver Queen

One of Oliver’s only regrets is not telling his (now) wife that he loved her sooner. And besides the sweet sincerity of that statement, there’s still a lot to unpack there.

Longtime watchers of Arrow know that the romantic plan wasn’t always Oliver and Felicity. For a short time, the plan was Oliver and Laurel, adhering to comic book canon.

And because the plan needed to change, there’s a lot of moments in the show where we can create valid arguments as to when Oliver fell in love with Felicity.

Whether any of these moments were scripted as having romantic undertones or not, the actors (Stephen Amell and Emily Bett Rickards) natural and undeniable chemistry created magic on our television screens, and consequently, the ship of dreams.

Moreover, Felicity has always been upfront about her feelings for Oliver before they were a couple, but there’s more speculation as to when Oliver returned those feelings for Felicity.

And folks, WE NEED TO TALK ABOUT IT!

Here’s five contenders for when Oliver could have told Felicity he loved her:

#1 First Meeting (1×03)

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This was when Felicity fell for Oliver, so it’s only right to assume he felt the same. But more importantly, this was when the audience fell for Felicity so it’s only natural that he was seeing what we were seeing! Right?! I can imagine Oliver doing a little chuckle, a sigh, and a smile, before saying “I love you” right after meeting her.

It would have been very Ted and Robin from How I Met Your Mother but still I’m not against it.

#2 Russia Sexual Tension (2×06)

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This is the first time Oliver and Felicity have a discussion about furthering anything romantic between the two of them. Oliver said he couldn’t pursue anything more than a casual relationship because of the life he leads. And Felicity just wanted a full and happy life for Oliver, even if it wasn’t with her.

He could of said “I love you” there, it would have been very season 3.

#3 There was no choice to make (2×07)

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So much subtext in this scene! Felicity is feeling guilty because Oliver killed someone to keep her safe, but Oliver feels he had no choice. Because he loves her. And he could have said so.

#4 You’re my partner (2×10)

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Oliver was confused by the feeling of jealousy when it came to his Girl-Wednesday and Barry Allen. And as he was explaining to Felicity that he didn’t realize how much he needed her, an “I love you” wouldn’t have been completely out of nowhere.

#5 I believe in you (2×22)

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In classic Felicity fashion, she gives Oliver a much needed pep talk in order to come up with a plan to stop Slade. We loved Felicity in that moment, and so did Oliver. He could have said it, I mean, why not?

My Verdict:

It’s fun to speculate when Oliver fell in love with Felicity, and when subsequently he could have told her so. But honestly, I don’t think there was ever one single moment that Oliver didn’t feel love for Felicity. I think the real question is when did he know it, and when did he trust the depth of his feeling. Felicity always knew what she felt for Oliver was love, but you can also speculate when she trusted the depth of her feeling as well.

Therefore, my personal head-canon has always been that Oliver knew he loved her in the clocktower (2×22), which is why the whole ruse worked, because he was telling the truth. However, he could have told her at any time before that. And that’s what Oliver regrets. Not having the extra time with the love of his life, and not being honest with himself and with her sooner.

And I could be wrong, Oliver could have known he loved Felicity in an off-screen moment while they were talking over some Big Belly Burger. He could have known during a moment in one of your fabulous fan fictions.

Loving Felicity Smoak is a constant state of being. For everyone. We just knew it before he did.

The final season of Arrow will return in the fall of 2019! Be sure to check out Pure Fandom’s Spotify for the Olicity Playlist, and for our website for all new Arrow coverage!

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Lynsey Neill

Lynsey is a Hufflepuff with Ravenclaw tendencies. Find her watching anything from BoJack Horseman to Grey's Anatomy. She loves to read... especially if it features dragons. If you ask her what she's doing she will most likely respond "I probably should be writing." Find her on Twitter @lynsneill, to theorize, geek out, and to obsess about Olicity.

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