The ways we flirt are influenced by the world we grew up in. But some things are universal.

Flirting is one of the most human impulses there is. Even the word’s etymology points to how long we as a species have been doing it: it stems from the 17th century French idiom “conter fleurette,” meaning telling gallantries.

Flirting is an evolutionary necessity. It’s the peacocking that leads to relationships, which (crudely put) lead to reproduction.

Obviously, having children is far from the only reason people pursue sexual or romantic relationships, but the point stands: flirting is a quintessentially human – or well, animal – behaviour.

All generations flirt, of course, but their approaches may naturally differ. It makes sense. For Baby Boomers and Gen Xers, flirting as young people, they would possibly have had to call a love interest’s home (and actually talk to their parents) or meet at dances.

Millennials will have started their romantic lives meeting people in bars and frat parties, before pivoting en masse to The Apps. Digital native Zoomers may have only known the DM slide for a large portion of their lives, and are now increasingly craving in-person dating experiences. Not to mention the impact of cultural shifts in gender and relationship politics on people’s flirting habits.

Everyone, whether they were 18 or 79, wanted to be seen, respected and listened to. They didn’t want their boundaries crossed. They wanted to laugh and have fun.

While there may be extensive discourse about the differences between generations in a world that’s fast-evolving, it’s important not to forget our shared humanity. At the end of the day, we’re all just looking for connection.

Boomers

The flirting advice I received from baby boomers (aged 61 to 79 in 2025): “Be yourself and be respectful.”

For Michael Swerdloff, a 64-year-old counsellor, coach and reiki master who dates women, being your authentic self while flirting is paramount.

“They will eventually get to meet you, why not now?” he asked, adding, “Try your best not to emulate how flirting takes place in movies and TV. It is not natural or authentic and is much harder to do than it looks on the screen.”

Swerdloff also stressed the importance of gauging a person’s interest and comfort level, through body language and verbal responses. He said to tap out if the interest doesn’t seem like it’s there and to continually seek consent as an encounter progresses.

Fellow Boomer Kim Airs, 67, a sex educator, loves a good pickup line, because they correspond with her personality. In the checkout line at a grocery store, “I’ll say something like, ‘I bet you live by yourself, right? Anyone with that many frozen foods usually means that!’ And I chuckle and acknowledge I shop the same,” she shared.

This approach is Airs being herself, but you should only attempt pickup lines if they feel in line with who you are. “That means not putting on a persona or a mask (exaggerating parts of you or hiding parts),” said relationship coach Shelley........

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