I've been dreaming of Boston. Not Boston now, and not Boston from before. It’s another Boston. It’s the way things would be if there was never a Gilead.
THE HANDMAID'S TALE | season 6, episode 10

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I've been dreaming of Boston. Not Boston now, and not Boston from before. It’s another Boston. It’s the way things would be if there was never a Gilead.
THE HANDMAID'S TALE | season 6, episode 10
THE HANDMAID'S TALE 2.08 "Women's Work" 4.02 "Nightshade"
She finally got to keep her baby, it was all she ever wanted 😭😭😭
THE HANDMAID'S TALE Season 6 Teaser Trailer
The Handmaid’s Tale Timeline
Thanks everyone for your comments. I’m going to dig a little deeper into the data.
So what do we know or suspect?
• June was born in 1983. She mentions her age (34) in episode 2x02.
• Luke was born in 1980, mentioned in 1x06.
• According to fan wiki, Nick was born in 1990, but this was never confirmed in the show.
• Janine was born on September 30, 1992 — this is written on her file in 4x08.
• Hannah was born in 2009, according to June’s documentation. In 5x03, it’s mentioned that Hannah is 12 years old.
• Nichole/Holly was born in 2017, according to June’s records.
• Angela/Charlotte was born at the beginning of Season 1 and is still very little at the end of that season when June finds out she’s pregnant. We can assume Angela is about a year older than Holly, born in 2016.
• Caleb’s birth date is unknown, but in Season 3 it’s mentioned that he died four years ago, already as a child of Gilead. It’s also said it’s been five years since the women became Handmaids (3x10).
• When June gets to Canada, it’s mentioned that she had spent seven years in Gilead.
• June returns to Canada and Serena finds out she’s pregnant in Season 4.
• Noah is born at the end of Season 5 and still appears very young at the end of Season 6. Nick tells June in Season 5 that Rose is pregnant, and in Season 6 she still hasn’t given birth — so the time gap is less than nine months.
What does this suggest?
• Hannah was five years old when she was taken from her family. By the end of the series, she would be 13.
• Holly should be 5 years old by the end of the series, and Angela should be 6. However, Holly definitely doesn’t look like a five-year-old in Season 6.
• Gilead apparently came into existence around 2014, and June stayed there until 2021.
• At the beginning of the story, June had already spent two years in her first placement.
• Season 1 takes place in 2016. Season 2 in 2017.
• Season 3 would be in 2019, so she could have stayed with Lawrence for around two years.
• By Season 4, it should already be 2021, when June arrives in Canada. But that feels like too long a period for how much story space is actually covered.
• Seasons 5 and 6 appear to take place between 2021/2022.
• By the end of the story, June should be 39 years old, Nick 32, and Janine 30.
What definitely doesn't fit in the story?
• In 6x07, a date (26/11/2024) is visible in Nick’s car — but in the context of the story, it couldn’t possibly be 2024. It’s most likely just the actual filming date.
• In 4x08, June says she came to the Waterfords in 2017 — but that doesn’t make sense, as that’s also the year when Holly was supposed to be born.
• And as I mentioned, Holly doesn't match her supposed age in the story at all.
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