Arrow: 4 times Oliver wanted to marry Felicity and the 1 time she proposed (2023)

The end of a year is a fun time to look back at all the wonderful things that have happened. And since it’s still December and it’s still the wedding anniversary month of Oliver Jonas Queen and Felicity Megan Smoak, it’s a great time to remember the many times the former billionaire playboy, who in his younger years was allergic to monogamy or commitment, couldn’t wait to “wife up,” as kids say these days, his brilliant and beautiful partner.

Arrow: 4 times Oliver wanted to marry Felicity and the 1 time she proposed (1)

It started, of course, with the ring in the soufflé.Barely five months after Oliver and Felicity left Star City together so he could re-discover who he had become after his Arrow identity was taken away and his stint with the League of Assassins, Oliver was ready to make it official. The former vigilante who made criminals tremble in their shoes prepped the evening with a home-cooked meal elaborate enough for his girlfriend to describe it as a “production,” with personal soufflés as the pièces de résistance. Of course, Felicity’s had an extra ingredient — a diamond ring once owned by Moira Queen. Unfortunately, while Oliver was in the kitchen nervously practicing his speech, duty called in the form of Ghost-ly trouble. In newly renamed Star City, Oliver started rethinking things after he and Felicity got pulled back in the dangerous vigilante life. He may have hidden the engagement ring in a bowl full of green stones at the end of the Season 4 premiere, but the idea of an Olicity wedding was already out there in the universe.

Arrow: 4 times Oliver wanted to marry Felicity and the 1 time she proposed (2)

1. ‘Felicity Smoak, would you make me the happiest man on the face of the Earth?’

After Donna Smoak found Oliver’s ring in a box of Christmas decorations and Curtis Holt’s husband mentioned how straight people hide engagement rings in pastry, Felicity started putting the pieces together and realized Oliver almost proposed three months ago. When asked about it, Oliver assured his girlfriend that he didn’t change his mind about wanting to marry her. It was more about how their circumstances had changed. Felicity pointed out that she chose this life and him. She knew what she was getting into. “I don’t understand why we can’t have both,” she told Oliver. His response was put on hold when Damien Darhk arrived and took Felicity, Diggle and Thea. Later, in Felicity’s cell, they talked about the meaning of marriage — “get through the hard times because we’re together, not in spite of it.”

With all this setup, it was no surprise when Oliver pulled Felicity on stage with him at a Christmas tree lighting event. After thanking everybody, Oliver singled out the one person in particular he was grateful for — “someone who has stood beside me when times were darkest. She is the one who lights my way.” Then, in front of family, friends — even an ex! — and supporters, Oliver Queen got down on one knee and, with his heart in hand, asked Felicity Smoak to marry him. She happily said yes.

Arrow: 4 times Oliver wanted to marry Felicity and the 1 time she proposed (3)

2. ‘For better or for worse’

But Oliver and Felicity’s celebration was short-lived. Darhk had his Ghost minions attack the couple’s limousine, killing the driver and grievously wounding Felicity. While his fiancée was undergoing surgeries, Oliver was pounding the streets, beating up people in the hopes of finding a lead on Darhk. He wanted the villain “off the board” before he went to see Felicity. He wanted to be able to tell the woman he loves that Darhk would never ever hurt her again. And while Felicity understood Oliver Queen and his demons, understood this fierce need of his to protect, there was a small part of her that wondered if her paralysis had made him change his mind. So she offered him an out. Because they hadn’t said their marriage vows yet, “for better or for worse doesn’t really apply here,” she told Oliver. It likely didn’t help that her ring was no longer on her finger when she woke up. Drawing the ring from his pocket, Oliver explained that a nurse had taken the precious piece of jewelry off Felicity in the emergency room — “how dare she.” Putting the ring back on Felicity’s finger, Oliver vowed, “For better or for worse.”

Arrow: 4 times Oliver wanted to marry Felicity and the 1 time she proposed (4)

3. ‘Will you marry me?’

In the back half of Season 4, after Felicity turned her father in to the authorities, after Oliver cut off Malcolm’s hand, when Thea and Andy were both “better” and things were quiet on the Darhk front, Oliver signaled he didn’t want to wait anymore. He asked Felicity to marry him — again. “I think I already answered that question,” she responded with a smile, flashing her ring.

(That line is notable because it’s the same line the Dominators used to confuse Oliver Queen during the show’s 100th episode and keep him in the altered “reality” where he never got on the Gambit, the boat never sank and his parents were both still alive. Hear this, Felicity Smoak is the only woman Oliver Queen wanted to marry. That’s why Felicity’s line was used for another woman. The Dominators were dumb, though. They would have been better served putting Oliver with Felicity in Bali. That would have ensured Oliver would never want to leave.)

Arrow: 4 times Oliver wanted to marry Felicity and the 1 time she proposed (5)

4. ‘Felicity Megan Smoak, will you marry me?’

After a long and torturous journey (for them and for Olicity shippers), Oliver and Felicity finally got back together during the early part of Season 6. They were living together. Felicity and Oliver’s son, William, had hit it off. They’ve walked in each other’s shoes. They APPEARED ready for that next, long-delayed step.

After Barry reminded Oliver that people like them were always going to get into trouble so there’s no sense in waiting for a good time, Oliver decided to make things official with Miss Smoak again. At Barry and Iris’ rehearsal dinner, Oliver broached the idea of him and Felicity doing something similar — crabcakes and toasts and, more importantly, rehearsing for the thing they would do the next day. But Felicity said no. Because she and Oliver still had some unresolved issues: she had planned a wedding once and everything went to hell in a hand basket so she’s scared, he’s still a little bit insecure and sees legally binding her to him in marriage as a necessary step in moving forward (I relish the irony of Oliver “I’ve jumped on boats and planes to avoid commitment” Queen being so eager to get married).

And this is why I and many fans out there point out that Oliver and Felicity’s love story was at the heart of “Crisis on Earth-X.” Both characters had emotional journeys they needed to take to get to what the proposal in the “Supergirl” episode set up — a wedding. Specifically, THEIR wedding. Oliver’s arc ended when he realized that nothing matters except that he loves Felicity, that he didn’t need anything else, he didn’t even need to get married. “I just want to be with you, OK?”

Arrow: 4 times Oliver wanted to marry Felicity and the 1 time she proposed (6)

‘Would you marry us, too? Will you marry me?’

Felicity’s arc took a little longer. After suggesting to Barry and Iris that John Diggle could be their officiant, Felicity realized that while she didn’t really believe in marriage, she believed in Oliver and she believed in their love, “married or unmarried.” She asked Oliver to marry her, telling him that her biggest fear in life was losing him. Before she could say more, Oliver eagerly said yes. They didn’t need to exchange vows, not really. They already had bared their souls during the fake wedding two years ago to trap the crazy archer lady. Oliver did take time to repeat his assertion that Felicity is the very best part of him — “I’m a better human being just because I’ve loved you.”

Arrow: 4 times Oliver wanted to marry Felicity and the 1 time she proposed (7)

And so before Digg — “I’m the guy who for the past six years had been trying to keep you two together. It’s only fitting that I’m marrying you” — Oliver and Felicity finally tied the knot.


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