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Malcolm is dead by Oliver’s hand (and was never a good father by any definition) and Moira is under indictment and imprisoned.
So when it comes to telling family, the only real person Oliver and Tommy have left is Thea.
(Felicity refuses to talk about it and threatens their trust funds when they try. She'd do it, they know; after one particularly bad argument Oliver unwillingly donated $20,000 to the spotted owl sanctuary. She says donkeys are next.)
They’ve been together for four months and the only person not involved who actually knows about it is John Diggle. (Keeping anything from the man is impossible. Tommy swears he’s psychic, Oliver puts it down to experience and insight and Felicity never expected to keep it from him to begin with. She's the only one with sense after all, both of the boys agree.)
And so they come up with a plan to tell Thea.
"But why does it have to be me?"
It's a rare day when Oliver “The Arrow” Queen sounds like a whiny teenager but he’s selling it today.
“One, she's your sister.” Felicity ticks off the points on her fingers, “two, if she thinks of me at all it's as the chick who brought flowers to your step-dad’s hospital room. Three, there's that time she made a pass at Tommy so that rules him out.”
“Wait, I never told you that.”
“It was a guess. Glad my insight hasn't failed me.”
“Hold on, my sister made a pass at you?”
Silence rules.
“No.”
“Of course not.”
Oliver blinks.
“But you said -”
“Joke!” Felicity says, slightly too quickly, “Totally a joke. Entirely a joke. So, when are you talking to Thea?”
“Sooooo, you’re telling me,” Thea says, brow furrowed, “that you're sleeping with Tommy?”
“Yes.”
“Annnnnnd, you’re sleeping with your secretary.”
“My assistant, Felicity, yes.”
“And Tommy’s okay with this?”
“Well, yes,” Oliver admits, “because he’s also sleeping with Felicity.”
Thea blinks.
“At the same time?”
“Yes, at the same time.”
Thea considers. Oliver holds his breath.
“Cool.”
Oliver blinks.
“Seriously?”
“What?” Thea says, “I've been waiting for you to kiss Tommy for, like, years, but I always thought it would end badly. Like flames and bullets badly. If this Felicity is the thing that means you both get to be happy, then I'm cool with it. Does she like shoes?”
“She likes shoes,” Oliver confirms, “why?”
“Because I am totally taking her shopping,” Thea grins, “you mean to tell me there's a chick out there with the inside track on you and Tommy? This girl I'm gonna love.”
Oliver nods and agrees and tries not to think about how his entire life just flashed before his eyes.
Felicity and Thea together.
Could the world survive?