From the start, Oliver and Felicity’s relationship on Arrow is one that has existed on a strong foundation of trust. It’s the hallmark of their relationship, and it’s made them the people and the couple they are at this point in their lives.
But one wrong decision on Oliver’s part has challenged that trust that has been cemented and evolving for four years now. While this might seem like a complete and utter setback for their relationship, this is a challenge that will test their relationship and ultimately prove to both of them that – should they survive this, and we know they will –their relationship is stronger because of it.
While Oliver and Felicity have been perfect for each other, that doesn’t make them perfect all the time. They are susceptible to mistakes. Does it make those mistakes right? Of course not, but a huge part of structuring a healthy relationship is experiencing hardships like this, dealing with the consequences, and improving because of it.
We knew this was coming. We knew this was coming, and yet it still hurt like hell when we watched Felicity remove her engagement ring, set it on the table, and literally walk out on Oliver as we head into a three-week hiatus that I thought couldn’t get much worse until now.
While things might seem dark and hopeless, make no mistake this is something that needs to happen if Oliver and Felicity are to emerge the stronger from this situation. I would actually be more concerned if this break up didn’t happen.
But I always harken back to this line that Oliver uttered to Felicity in the season premiere:

For Felicity, this situation has nothing to do with the fact that Oliver has a son and everything to do with the fact that he lied to her about something so significant in his life. They are (sorry, were *cries*) engaged and, like Felicity told Oliver back during the Flarrow crossover, this is something that he should want to tell her. Marriage is about partnership, and trust is a huge part of that. Being partners is about communicating with each other and making decisions as a team instead of individually. Felicity might not be William’s birth mother, but as Oliver’s fiancée and future wife, she deserved Oliver’s respect and trust when it came to making the decision about whether or not William was a part of his life.
In no way do I fault Felicity for making the decision to take a break. This makes complete sense for her character. Felicity is someone who has trust issues brought about by her father’s abandonment and her ex-boyfriend Cooper. In fact, it’s a Smoak women trait as we’ve seen the importance of trust to both Felicity and her mother. Trust is more than a word. It’s a promise. And right now Oliver broke that promise.
This is a lesson that Oliver needs to learn. We often forget that Oliver wasn’t the man he is now with Felicity. Oliver is someone who has lied countless times in his life, whether it was in the past with Laurel, in the past on the island, or now in the present with Felicity. But Oliver never learned his lesson. It’s a repeated cycle because of the fact that he never learned from his mistakes.
But this is the time when Oliver is going to learn that hard lesson and grow the stronger for it. He’s going to man up, take ownership of his mistakes, accept the consequences, and earn Felicity’s trust back. It’s all part of his hero’s journey and Olicity’s love story.
I’ve always felt – and Oliver admitted it to Thea, as well – that Oliver and Felicity couldn’t get married with this huge lie hanging over their heads. And the same goes with the fallout. They cannot get married with this distrust in their relationship. So taking a break – really thinking about their relationship and how important it is to them – is something that they need to experience. It’ll only serve as a good thing moving forward.
So while you might feel tempted to embrace the sadness and hopelessness that comes with Oliver and Felicity’s temporary break, remember that this is something that needed to happen in order for these two soulmates to get through this. And they will get through this.
Arrow has proven countless times – and will continue to – that Oliver and Felicity are the epic love story of this show. Oliver cannot become the hero he’s destined to be without Felicity, and Felicity cannot become the hero that she’s destined to be without Oliver. They make each other better. But they’re not perfect. And perfect is boring. You need challenges to grow as individuals and as partners. Plus, when Stephen Amell says that he doesn’t see Arrow without Olicity then you pretty much have all the assurances that you need right there.
True love stories aren’t easy. True love stories aren’t without their hardships. True love stories are worth fighting for, sufferings and all.