About 5 months after Lisa's wedding, the Waverider crew finds themselves on a mission in Siberia in 1892. There's a small part of Leonard that finds this strangely familiar, but he chalks it up to impending fatherhood messing with his head.

"Assassin! I'm heading out for a bit of fresh air," he calls to Sara.

"Siberia's calling to Captain Cold, eh? Be back soon!" she replies.

Leonard wanders into the trees near the ship when he feels the arrival of a speedster.

"Hello, Flash."

He agrees to help Barry (ah, love) and suddenly he finds himself being whisked away to 2017 (the very timeframe in which he was dead), helping Barry Allen (of all people) break into ARGUS (of all places) to steal an alien power source (of all things).

He gets a bit of satisfaction confusing Barry by asking to not be placed at the singles' table at the wedding. And he loves the awkward looks and hushed voices of those thinking he's still dead.

Though, Leonard has never felt so worried about dying as he does while trapped in that room with King Shark. If he dies here, Sara will never know where he went. He didn't expect anything this dangerous with do-gooder Barry around, so he didn't mention that he was leaving. He just expected to be returned to the same time and place. And now he fears abandoning her once more. He's fairly certain she won't be as forgiving this time. Especially with their baby on the way. He vows to himself that he'll never pull anything so ballsy again.

But thankfully, Cisco hacks into the system and Barry pulls him out. The shark's detached hand is a painful reminder of his past and how his future could have been ruined. But as he walks back to the Waverider, he chuckles to himself about the confused look on Barry's face when he said, "No strings on me."

"Heh, let him figure that one out for a while," he mutters to himself.

Sara smiles as Leonard walks back to the Waverider.

"Have fun on your playdate with Barry?" she jokes.

And now Leonard knows why he found the day feeling so familiar. This whole thing.

He finishes making the video for his sister and watches it back. This is how Lisa always seemed to have something hanging over his head, especially concerning his relationship with Sara. Leonard notes that he smiles up at Sara at one point in the video and there's a tiny second of a glimmer of his wedding band too. Lisa was certainly no dummy and she must have picked up on all of that. She's likely known since 2017 that he's alive and married and she's never told him. Maybe she did know a thing or two about time travel. Or Ramon had advised her to keep quiet. That crew knew all about the dangers of changing time.

As Sara prepares the disc for delivery, Leonard sits back. "Observant little sneak," he mumbles.