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Elly Miles dated one contestant before, plus everything else we know about her relationships.

Earlier this month, we were introduced to the (very beautiful) men that are vying for the hearts of The Bachelorette(s), Elly and Becky Miles.

There's a football player, a travel influencer, and — naturally — several models.

But before we spend the next 1,378 hours watching which blokes the sisters choose, let's look back at the relationships that came before.

Today, we start with 25-year-old nurse Elly.

Watch: The Bachelor contestants: Translated. Post continues below.


Video via Mamamia

Elly was a front-runner on Matt Agnew's season of The Bachelor, where she described her ideal partner as someone "kind, funny, selfless, loyal and intelligent".

"[I'm looking for] someone I can learn from and who learns from me. Supporting each other through both the difficult and happy times. Someone who shares the same love for life as me and who is willing to take chances. 

"Someone to travel the world and tick off my bucket-list with. Someone who my family loves and I love his. Someone who, if they have a dog, that their dog and my dog get along really well. Someone generous, family orientated and humble."

So we took a deep stalk all the way back through Elly's social media to uncover her past relationships, and hopefully get a clue into what men may succeed this season — if the past is any indicator.

Here's what you need to know.

Elly's high school sweetheart.

A very deep dive into Elly Miles' Instagram reveals that the NSW woman's very first love was her high school sweetheart, Tom Caldwell.






View this post on Instagram









#boyf and I at my #grad #wooooo xoxoxo

A post shared by  E L L Y S M I L E S (@ellymiles) on

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One of Elly's first posts back in 2012 showed the pair at her Year 12 graduation, and (if my maths is correct) they had been together for a year already.

Elly shared several more pictures with Tom, celebrating birthdays and anniversaries, before the posts came to an end just after her birthday in 2015.

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The pair were together for over four years, based on Elly's insta activity. 

We wonder how he's doing now...

A current Bachelorette contestant.

The So Dramatic! podcast has leaked all the information we needed to know about one of Elly's exes, Joe Woodbury. And it turns out, he'll be appearing on this season of The Bachelorette.

"They knew each other from Newcastle before the show," So Dramatic! host Megan Pustetto started. 

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"[They] didn't only know each other, they used to date." 

"Elly and Joe dated for a couple of months just before The Bachelorette. They had been on and off, dating in Newcastle right up until she moved to Bondi. They then continued dating casually and she would travel back and forth between Bondi and Newcastle."

According to the famously well-sourced Pustetto, "It wasn't a secret at all."

"Elly actually requested he be cast on the show."

If you watch The Bachelorette's first trailer to the end, you'll see the moment they recognise each other on the red carpet.


Reportedly adding to the theory are a few comments on Joe's Instagram from back in April (he's currently on private so we cannot confirm or deny).

"Elly commented on one of Joe's pictures from April, writing: 'What an iso crew' to which Joe replied: 'Just missing dobby," Megan claimed.

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Apparently, "dobby" is Joe's nickname for Elly...

The Bachelor Matt Agnew

Matt Agnew is Elly's most notable ex — you know, being The Bachelor and all.

Elly made it to the top five of his 2019 season and was a fan favourite to win. 

Her shock elimination caused a big uproar, so much so that fans quickly petitioned for her to be The Bachelorette

Matt ultimately ended up with Chelsie McLeod, which Elly thought was the right decision.

"He’s a bit of a city slicker and I’m a country girl, I guess I was a little bit concerned that we were too different in that aspect," she said in an interview with Mamamia last year.

"I was scared to let myself go falling in love with him if we just weren’t going to be right for each other down the line because of those reasons. 

"We were too different."

Feature Image: Instagram / Ellymiles

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