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When I was in my second year of university, a stranger approached a friend and me on the streets of Melbourne, asking to photograph us for his website about interracial couples.

A little taken aback, we told him we weren't together but had friends that might fit the bill.

"Oh, sorry," I remember him saying. "I only take photos of interracial couples with an Asian guy and a white girl."

He wasn't Asian himself, and I wasn't sure if that made things more or less weird.

He went on to explain that many of his friends were Asian men who thought Anglo-Australian women just weren't interested in dating them. His website was his way of showing this wasn't true.

After a fittingly awkward goodbye, I never saw that man (or, concerningly, his website) again, but the unusual encounter stayed with me.

It was the first time someone had given voice to an insecurity I held but had never felt comfortable communicating.

When my ethnicity crashed into my dating life

My first relationship was with a Western girl when I was growing up in Perth, and I never felt like my race was a factor in how it started or ended.

I identified with Western values over my birth country of Singapore in almost every aspect of my life but food (rice > bread). I was generally drawn to Western girls because I felt we shared the same values.

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At the time, I rarely felt that assumptions were made about me based on my ethnicity, but things changed when I moved to Melbourne for university.

In a new city, stripped of the context of my hometown, I felt judged for the first time, like I was subtly but surely boxed into an "Asian" category.

So, I consciously tried to be a boy from WA, to avoid being mistaken for an international student.

Since then, my experience as a person of colour in Australia has been defined the question: "Is this happening because of who I am, or because of what people think I am?"

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It's a never-ending internal dialogue that adds complexity and confusion to aspects of life that are already turbulent — and dating is where it hit me the hardest.

I couldn't shake the feeling that I was working against preconceptions and presumptions when dating people outside my race. It felt like I had to overcome barriers that my non-Asian friends didn't have to, and that cost me a lot of confidence over time.

I'm in a relationship now, and my partner is white. Talking to her about the anxieties I experienced around dating, it's easy to feel like my concerns were caused by internalised racism and problematic stereotypes that I projected onto the world around me.

But I also know that those thoughts and feelings come from the comfort of our relationship.

So, I decided to start a long overdue conversation with other Asian men, to find out if I was alone in my anxieties.

When it comes to dating, what's the biggest challenge you've faced? And how did you overcome it? Email life@abc.net.au.

Distancing yourself from your background, through dating

Chris Quyen, a university student, photographer and creative director from Sydney, says his early interest in dating was influenced by a desire to fit in.

"There's always this subtle pressure to fit in and assimilate, and when I was growing up, I thought the best way to assimilate was to date a white person," he says.

That led him to downplay his background and present himself as something else.

"Through that stage of my life, I wore blue contacts, I dyed my hair blonde, I spoke with a very Aussie accent … I'd try to dispel my own culture," Chris says.

For Melbourne-based hip-hop artist Jay Kim, this approach to dating is understandable, but not without its problems.

"I don't think that the single act of dating a white woman should ever be seen as an accomplishment," he says.

"[But] the whole idea of an achievement can come from this feeling of … not being good enough, because you're doing something that people aren't expecting."

The impact of representation and fetishisation

Dating coach Iona Yeung says Asian men are represented largely through "nerdy stereotypes" in the media, with few positive role models to draw confidence from when it comes to dating.

Chris agrees, saying the media plays an "important role in informing who we are attracted to". When it comes to Asian men, they're often depicted as "the bread shop boy or the computer genius who helps the white male protagonist get the girl," he says, if they're represented at all.

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For Jay, in-person interactions have impacted his confidence.

"When I had my own queer experiences, I started to realise that I was overhearing many conversations about the fetishisation of Asian men," he says.

An interaction with a female partner who called him "exotic" similarly affected his sense of self.

"What that did was form this expectation in my mind that … it was just out of experimentation and out of trying new things, as opposed to me being really attracted to or desired," he says.

Finding confidence and taking care

Having these conversations has helped me realise that although my anxieties around dating come from my experience with sex and relationships — they're also connected to how I value my culture.

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It's fitting that some of the people I spoke to have embraced their backgrounds as they negotiate the challenges that come with dating as Asian Australian men.

"I've tried not to make my race a burden and instead use it to make myself more interesting," Chris says.

"I think it's up to us to take it onto ourselves and really share our culture with other people as loudly and as proudly as possible."

For Jay, "practising a lot self-love, practising a lot of empathy for others, and being around the right people" has allowed him to appreciate moments of intimacy for what they are, and feel real confidence.

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Dating coach Iona says finding role models and references to bolster your confidence is key to overcoming concerns or anxieties you might have around dating.

"It's all in the mindset, and there's a market for everyone," she says.

My advice would be not to wait seven years until you talk to someone about your feelings or concerns, and certainly not to wait until a stranger on a street approaches you for a suspicious-sounding website you later can't find to have this conversation with yourself.