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Need To Know > Lifestyle > ‘I told my girlfriend I crossdress on our FIFTH date – I thought she’d dump me’
A man was convinced his new girlfriend would dump him when he admitted he was a crossdresser on their fifth date - but her reaction felt like a dream.
Lifestyle

‘I told my girlfriend I crossdress on our FIFTH date – I thought she’d dump me’

Hannah Phillips
Last updated: September 25, 2026 10:27 am
Hannah Phillips Published September 25, 2026
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Julia with his girlfriend. (Jam Press/@juliasometimes)
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A man has revealed how he nervously told his new girlfriend he was a crossdresser – despite being convinced she’d dump him.

The 29-year-old, who goes by Julia when dressing as a woman but identifies as a man, had been crossdressing for around nine years when he met his now-girlfriend, 24.

As their romance became more serious, Julia decided he needed to reveal the side of himself he had previously kept private.

READ MORE: ‘I thought pricey wine made my drinking sophisticated – I was on three bottles a night’

He was “terrified” she would reject him and even believed there was a good chance the revelation would end their fledgling relationship.

But instead, her reaction left him feeling like he was in a “dream”.

“The fifth date might sound very early, but by then I already knew I really liked her and could see our relationship becoming something serious,” Julia, from the Netherlands, told Need To Know.

A man was convinced his new girlfriend would dump him when he admitted he was a crossdresser on their fifth date - but her reaction felt like a dream.
Julia. (Jam Press/@juliasometimes)

“I didn’t want to build a future together while hiding such an important part of myself.

“I felt she deserved complete honesty from the beginning.

“If she couldn’t accept this side of me, I wanted to know before we became even more emotionally invested.

“I was terrified.

“I genuinely believed there was a good chance she would end the relationship.

“Crossdressing is something many people don’t understand, so I imagined every possible worst-case scenario.

“Looking back, I had built it up much more in my own head than I needed to.

A man was convinced his new girlfriend would dump him when he admitted he was a crossdresser on their fifth date - but her reaction felt like a dream.
Julia in an earlier photo before he began cross-dressing. (Jam Press/@juliasometimes)

“Being that vulnerable with someone you care about is one of the hardest things I’ve ever done.”

Julia first explained what crossdressing meant to him and why he enjoyed it before showing his girlfriend photographs of his feminine alter ego.

But rather than rejecting him, she wanted to understand more.

Julia said: “Her reaction honestly felt like a dream.

“She was surprised, which I completely understood, but instead of judging me she became curious.

“She listened carefully, asked thoughtful questions and genuinely wanted to understand what crossdressing meant to me.

A man was convinced his new girlfriend would dump him when he admitted he was a crossdresser on their fifth date - but her reaction felt like a dream.
Julia with his girlfriend. (Jam Press/@juliasometimes)

“I’m incredibly grateful for the way she handled everything.

“She grew up in a very open-minded family, and I think that played a big role.

“She never made me feel strange, embarrassed or ashamed.

“I honestly couldn’t have wished for a better response.”

Julia says the conversation ultimately brought the couple closer together.

He said: “Looking back, that conversation made me realise how lucky I am to have someone who accepts every part of who I am.

“The biggest surprise was discovering how accepting people can be when you give them the chance to understand.

A man was convinced his new girlfriend would dump him when he admitted he was a crossdresser on their fifth date - but her reaction felt like a dream.
Julia. (Jam Press/@juliasometimes)

“I expected rejection, but instead I found support from my girlfriend, from friends and family, and from thousands of people online.

“It completely changed my perspective on vulnerability.

“Sometimes the thing you’re most afraid to tell someone ends up bringing you closer together, and that’s exactly what happened to us.”

Julia believes being open early in a relationship was ultimately the right decision for him.

He added: “Every situation is different, so I don’t think there’s one perfect answer but if you truly see a future with someone, I believe honesty is the strongest foundation for a relationship.

“Keeping such a big part of yourself hidden becomes emotionally exhausting.

A man was convinced his new girlfriend would dump him when he admitted he was a crossdresser on their fifth date - but her reaction felt like a dream.
Julia with his girlfriend. (Jam Press/@juliasometimes)

“Telling my girlfriend was one of the scariest conversations I’ve ever had, but it also turned out to be one of the best decisions I’ve ever made.”

Julia says crossdressing has become an increasingly important creative outlet over the past five years as his interest in fashion and make-up has grown.

He said: “What started as curiosity slowly became a creative outlet and an important part of who I am.

“For me, it’s not about wanting to become someone else. Most of the time I simply live my everyday life as a man.

“Julia is another side of me that allows me to express creativity, confidence and femininity through fashion, makeup and photography.

“One of the biggest misconceptions is that crossdressing is always sexual, but for me it isn’t.

(Jam Press/@juliasometimes)

“It’s simply a hobby and a form of self-expression that genuinely makes me happy.

“Sharing my journey online has also shown me how many people secretly relate to these feelings.

“That’s become one of the most rewarding parts of creating content.

“Sharing my story has actually become really meaningful to me.

“I receive a lot of DMs from people who say my posts have inspired them, helped them feel less alone or given them a little more confidence to accept this part of themselves.

“Some are taking their own first steps or thinking about opening up to someone close to them.

“Those messages genuinely mean a lot to me.

“If sharing my own journey can help even one person feel a little more comfortable with who they are, then I’m really happy I’ve been able to do that.”

READ MORE: ‘Forget designer clothes and flashy cars – I spend £2,000 a MONTH giving my cats a life of luxury’

A man was convinced his new girlfriend would dump him when he admitted he was a crossdresser on their fifth date - but her reaction felt like a dream.
Julia with his girlfriend. (Jam Press/@juliasometimes)
A man was convinced his new girlfriend would dump him when he admitted he was a crossdresser on their fifth date - but her reaction felt like a dream.
Julia. (Jam Press/@juliasometimes)
A man was convinced his new girlfriend would dump him when he admitted he was a crossdresser on their fifth date - but her reaction felt like a dream.
Julia. (Jam Press/@juliasometimes)

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