"I messaged girls for the first time."
Lilly Singh came out as bisexual in early 2019 with a simple social media post.
The caption simply read, “Female, Coloured, Bisexual” with a green tick next to each word, followed by a succinct statement:
“Throughout my life, these have proven to be obstacles from time to time.
“But now I’m fully embracing them as my superpowers.
“No matter how many “boxes” you check, I encourage you to do the same,” followed by five coloured heart emojis.”
One year later, in September 2019, Lilly posted a photo on Instagram on the first anniversary of her coming out with a caption that better encapsulated her emotions.
Part of the statement read: “Coming out was one of the scariest experiences of my life.
“I’d love to tell you that everyone was supportive and that people didn’t treat me differently but I’d be lying.
“Coming out lifted a weight off my shoulders but at the same time, it placed the weight of judgement on my chest.
“Maybe that’s the culture I was raised in or maybe it’s all in my head but either way for me it’s real.”
Today, Lilly Singh is a lot more secure in her identity but continues to maintain a layer of secrecy when it comes to her relationships, be it with men or women.
She did, however, provide a rare glimpse at how her dating experiences have evolved since coming out.
In a conversation with Vogue, Lilly said: “A big part of it was learning how to flirt with girls, which is something I’d never done before.
“I downloaded dating apps for the first time; I messaged girls for the first time.
“It was strange because I was used to having girls as friends and now the whole dynamic had changed.”
Lilly’s rule for being with women is that the line between “just hanging out, doing girl things” and dating should never be blurred.
The YouTuber added: “I don’t want to get my nails done with someone I could potentially date.
“I don’t want to get dressed, drink and dance with them the way I do with my female friends.
“I don’t want to do my eyeliner in the mirror with them; it makes me want to die.”
Although Lilly Singh is clear about what she wants out of her relationships with women, this wasn’t always the case.
The comedian made some dating app faux pas when she first changed her sexual orientation preferences.
Lilly said: “The first time I messaged a girl on a dating app, I called her sis.
“I literally had to stop and chastise myself and be like ‘No. Bad.’ I’m getting better at it but navigating this new realm of flirting is still a work in progress.”