'He seemed to enjoy kissing me': Bruce Jenner's high school sweetheart breaks silence, admitting she's 'shocked' he's transitioning into a woman

Bruce was one of the best-looking and most accomplished students at Newtown High School in Connecticut in the 1960s.

And his high school sweetheart Michelle Rosenthal thought the now 65-year-old reality star was pretty special too, even letting him take her to the prom.

She told Inside Edition she is surprised to learn that the Keeping Up With The Kardashians star is transitioning into a woman, a secret he is expected to share with Diane Sawyer on Friday.

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His ex speaks out: Michelle Rosenthal told Inside Edition in an interview that is set to air on Thursday that she is surprised to learn her high school sweetheart Bruce Jenner is transitioning into a woman

His ex speaks out: Michelle Rosenthal told Inside Edition in an interview that is set to air on Thursday that she is surprised to learn her high school sweetheart Bruce Jenner is transitioning into a woman

The grown-up Bruce: Jenner, now 65, with his long hair at a charity event in NYC in September 2013

The grown-up Bruce: Jenner, now 65, with his long hair at a charity event in NYC in September 2013

'I would never have thought that in a million years, knowing him from high school,' the senior citizen told the TV show in an interview that is set to air on Thursday.

'When it came out in the paper that he was thinking of this, I think everyone was really shocked.'

She also shared that she was intimate with the former Olympian, who divorced E! producer Kris Jenner in December.

Close when they were teenagers: Michelle and Bruce at the prom at Newtown High School in Connecticut

Close when they were teenagers: Michelle and Bruce at the prom at Newtown High School in Connecticut

Look familiar?: Rosenthal had dark hair when she was in high school, resembling Bruce's stepdaughter Kourtney Kardashian

Look familiar?: Rosenthal had dark hair when she was in high school, resembling Bruce's stepdaughter Kourtney Kardashian

There is a resemblance: When Bruce dated Michelle, she looked a lot like his stepdaughter Kourtney Kardashian who is pictured here in an episode of Keeping Up With The Kardashians

There is a resemblance: When Bruce dated Michelle, she looked a lot like his stepdaughter Kourtney Kardashian who is pictured here in an episode of Keeping Up With The Kardashians

'We danced close, we did kiss. He seemed to enjoy it,' Rosenthal said.

In old photos she shared with Inside Edition Michelle is seen sitting next to a smiling Bruce, who does not at all resemble the thin, long-haired TV star he is today.

She looks different too with shoulder-length dark brown hair. In one photo she seems to resemble his stepdaughter Kourtney, 36. 

Today Michelle's hair is short and highlighted. This is the first time she has spoken about Bruce.

A strong athlete: Bruce was one of the best-looking and most accomplished students at Newtown High School

A strong athlete: Bruce was one of the best-looking and most accomplished students at Newtown High School

A shock: 'I would never have thought that in a million years, knowing him from high school,' the woman, who is in her sixties, told the TV show

A shock: 'I would never have thought that in a million years, knowing him from high school,' the woman, who is in her sixties, told the TV show

His old friends didn't see it coming: 'When it came out in the paper that he was thinking of this, I think everyone was really shocked,' added Michelle

His old friends didn't see it coming: 'When it came out in the paper that he was thinking of this, I think everyone was really shocked,' added Michelle

A different person back then: The old high school flame said that Bruce was happy and outgoing 

A different person back then: The old high school flame said that Bruce was happy and outgoing 

His old style: When Inside Edition correspondent Megan Alexander asks the woman if she was shocked with who Bruce has become, she said most definitely yes

His old style: When Inside Edition correspondent Megan Alexander asks the woman if she was shocked with who Bruce has become, she said most definitely yes

When Inside Edition correspondent Megan Alexander asks the woman if she was shocked with who Bruce has become, she said most definitely yes. 

'The Bruce I remember was happy go lucky,' the woman, who invited the show into her home for a sit down, said.

'Nice guy, friendly with everybody, popular. The few times I’ve seen him on the TV show, he just didn’t look happy.'

Talking about the past: 'The Bruce I remember was happy go lucky,' the woman, who invited the show into her home for a sit down, said

Talking about the past: 'The Bruce I remember was happy go lucky,' the woman, who invited the show into her home for a sit down, said

The way he was: 'Nice guy, friendly with everybody, popular. The few times I’ve seen him on the TV show, he just didn’t look happy,' she added

The way he was: 'Nice guy, friendly with everybody, popular. The few times I’ve seen him on the TV show, he just didn’t look happy,' she added

She sure is Keeping Up With The Kardashians: Michelle admitted she has seen the E! show and watched stories about him in the press

She sure is Keeping Up With The Kardashians: Michelle admitted she has seen the E! show and watched stories about him in the press

In the past several seasons of the popular E! show Jenner has been fighting with Kris and her three daughters Kourtney, Kim, 34, and Khloe, 30.

He has become more of a recluse as he tinkered with his toy helicopters and started highlighting his hair.

'I hope he figures out what it is that he would like in his life, and I hope he finds happiness,' Rosenthal added. 

Inside Edition's full interview with Bruce's ex airs on Thursday, April 23. Check local listings for stations and times at www.insideedition.com.

She has only good wishes for the TV star: 'I hope he figures out what it is that he would like in his life, and I hope he finds happiness,' Rosenthal said; here Bruce is pictured in an episode of Keeping Up With The Kardashians

She has only good wishes for the TV star: 'I hope he figures out what it is that he would like in his life, and I hope he finds happiness,' Rosenthal said; here Bruce is pictured in an episode of Keeping Up With The Kardashians

Bruce was last seen on Sunday riding his Harley-Davidson motorcycle in the Santa Monica mountains.

The former track star could be seen wearing a sports bra under his sweatshirt. 

RadarOnline reported on Monday that Bruce had breast augmentation.

'Bruce had silicone breast implants put in a few weeks ago,' Radar quoted an insider. 'He went with a smaller implant because he didn't want to look ridiculous.'

'Recovery hasn't been that difficult, but Bruce has had to sleep in a recliner to help with the healing,' the source said.

'He’s not allowed to lift anything, and he has to wear a bra 24/7, but he’s expected to resume normal activities in the next six weeks.'

The woman that made him a TV sensation: The former Olympian with Kris Jenner in April 2014; they finalized their divorce in December

The woman that made him a TV sensation: The former Olympian with Kris Jenner in April 2014; they finalized their divorce in December

'He has been emotional, but finally feels like this is the body he has meant to have,' they added.

As well as growing out his brunette locks, Bruce has already undergone a laryngeal shave procedure to flatten out his Adam's Apple, and has reportedly had rhinoplasty to sculpt his nose into a more feminine shape.

He has also been seen recently with painted nails and a fuller looking pout.

Sharing his secret: In a recent clip from his two-hour interview with Diane Sawyer, the reality star - who has six biological children and four stepchildren - revealed his brood are his biggest priority, saying: 'I can't let myself hurt them. They're the only ones I'm concerned with'

Sharing his secret: In a recent clip from his two-hour interview with Diane Sawyer, the reality star - who has six biological children and four stepchildren - revealed his brood are his biggest priority, saying: 'I can't let myself hurt them. They're the only ones I'm concerned with'

He must be nervous: 'My whole life has been getting me ready for this,' he told the 69-year-old reporter; his interview on ABC airs Friday

He must be nervous: 'My whole life has been getting me ready for this,' he told the 69-year-old reporter; his interview on ABC airs Friday

In a recent clip from his two-hour interview with Sawyer, the reality star - who has six biological children and four stepchildren - revealed his brood are his biggest priority, saying: 'I can't let myself hurt them. They're the only ones I'm concerned with.'

He is seen supported by his four oldest children Burt, 36, Casey, 34, Brandon, 33, and Brody, 31 who sit nearby as he chats with the ABC host.

'My whole life has been getting me ready for this,' he told the 69-year-old reporter.

They were off to a good start: Bruce and Kris with their combined kids during their wedding in 1991

They were off to a good start: Bruce and Kris with their combined kids during their wedding in 1991

The new teaser follows another clip, that promises 'the interview, the journey, the decisions, the future.'

Last month a source told People: 'Bruce's primary goal is to bring awareness to this issue in order to help others in the transgender community.'

The father of six 'wants this to be taken seriously so that his situation can have the most positive impact on society's perception of the transgender community,' the source added. 

Meanwhile, Kris, 59, has been dating music executive Corey Gamble and has been hitting clubs in Las Vegas. 

It's showtime East Coast!!! #KUWTK starts now!

A photo posted by @krisjenner on

 

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