6 Ways To “Drop The Hanky,” According To Real Men

“Dropping the hanky” was an old Victorian practice where women would literally drop their handkerchief within the proximity of a man they were interested in. The man would then pick it up and return it. Ingeniously, it would have been the perfect “in” at an event such as a ball (sidenote: please can we have more balls?) as it would signal to said gentleman that there was an opportunity to start a conversation.

Fast forward a good few centuries and let it be said that showing interest in a man does not take away his ability or power to pursue you. Rather, it gives him a green light that you are open to being pursued. 

Why Men Don’t Approach Women

“Women are gatekeepers,” one man told me. “We have an innate fear of rejection, and at some point, that can also become a fear of ridicule too. When a woman says ‘no,’ it almost makes us feel like we’re not good enough.” 

Another guy said it was complex. “We don’t want to come on too keen, or be too intense, but equally I don’t want to miss the opportunity or play it so cool the woman never realizes I’m interested.”

Situational context is another layer men have to keep in mind. “Some men clumsily copy others but don’t have the same self-awareness or desirability. For example, a pick-up line might be well received by women when it comes from an attractive man she’s interested in, but one-to-one at night at a bus stop with a stranger is only ever going to be intimidating.”

The consensus from the men I spoke with was a general fear of picking up something you are not putting down: “Guys can be a little dense sometimes, and we worry about getting it wrong. What if I think you’re giving me a sign, but you’re not and I just look like a weirdo?” 

So, as women, we need to master the art of encouraging men to ask us out in the first place, as well as learning to say “no” well, with clarity and grace. Here are six ways you can be more approachable and “drop the hanky”: 

1. Make Eye Contact

Making eye contact with someone you’re not directly speaking to is a fine art. You want to come across as alluring and intriguing, not creepy and socially awkward, so I get that this is a line to be walked with situational caution. But, the men I surveyed say that eye contact is the easiest way for a man to understand you want him to approach you and start a conversation: “Consistent eye contact or a smile should signal interest, but these days a lot of men either don't or can't read signs, or they flat out are just too shy to cold approach a lady, so don’t be shy to hold that eye contact just a little bit longer than feels natural.” 

And remember, don’t stop the eye contact when you’ve started speaking. This is when you can activate full flirtation mode. Classily, of course. “Pushing the hair behind the ear is a classic!” said one guy. “I feel like I can generally just tell when a woman is interested, there’s free flowing, engaging conversation and she’s laughing at my terrible jokes. She’s giving me eye contact and lots of smiling.”

Another man told me, “I think we humans are somehow able to deduce a lot just from someone's facial expressions, particularly the eyes. We can tell your emotion, intent, and state of well-being, so I guess that means we communicate pretty effectively through them too!”

2. Physical Proximity

Being in someone’s line of sight is the most surefire way of getting noticed, so the next time you see someone who’s caught your eye, try to make sure he can physically see you too. (And no, being behind him in the church pew is not a good place to be.)

One of my guy friends suggested, “Let's say you see a cute guy at a coffee shop, well, figure out a way to sit close to him so you’re within his field of view and he has the opportunity to notice you.”

“If a woman is physically near me in group social settings, I usually take notice that she might be hanging around for a reason,” another friend said. “It’s a good way for me to understand she may be open to branching off and having a one-on-one conversation.” 

3. Show Interest

Almost all the men I asked told me that having shared interests was a huge green light for them, as well as a woman being interested in something he cares about.

One man told me, “An obvious one would be if a woman has a common interest and drops a comment like: ‘I saw there’s a new exhibit at [insert museum].’ She’s not asking me out, but she’s almost suggesting that ‘Yes, we should go together!’”

Another said, “It’s so easy to learn so much about each other online/through texting that you can build a fantasy in your head that’s wildly different from reality, so actually speaking about shared interests helps to make our interactions feel more real.” 

A third recommended, “Show interest in my football team/TV show/band, even if it’s kind of forced. It’s a surefire clue for me!”

If you have a workplace crush, one of my guy friends explained, “If I’m interested in someone in a more professional setting, like at work or volunteering, it’s so helpful if the woman talks to me first about something unrelated and non-professional enough that I can take it to mean she likes talking to me. If I want to pursue her, that gives me the chance!”

4. Consistent Communication 

The three requirements of a healthy friendship are positivity, vulnerability, and consistency, so it’s no surprise that an element of steady communication or social interaction can help amp up a friendship to the next level. One man told me, “When messages like ‘Good morning, I hope you have a good day’ become frequent, or a woman checks in on my well-being, I know it’s more than just a male-female friendship.”

Another recommended, “Show interest by spending time with me. I’ll eventually get the message!”

A third guy said, “For me, it’s the level of communication. I have plenty of female friends. We catch up obviously, but I don’t have any level of constant communication on the daily with any of them. If a girl was talking to me regularly, that to me is an indication she might be interested.”

5. Drop Clear Hints

A conundrum that came up a lot was confusion over whether we’re dropping a hint or not. “The main issue I see is not knowing when is an appropriate time to approach a woman,” one guy stated. “When do women like being asked out?” While another admitted, “The real issue is men not taking chances because they aren't sure.”

So, ladies, consider this a public service announcement to drop hints with clarity.

“Obvious hints make me feel much more confident in asking a woman out because I know I’ll be able to plan a nice date that we both enjoy,” one guy said.

Another man advised, “If he doesn't pursue you straight away, don't be afraid to invite him somewhere that isn't fully a date but is exclusive enough in terms of attention to pique his interest.”

6. Give Him Space To Be Chivalrous

Personally, I notice instantly if a man walks on the outside of the sidewalk, offers to carry something for me, or opens my door. (Bonus points if it’s my car door he’s opening.) But, we also need to give the men in our lives the opportunity to be chivalrous, as well as communicate that we appreciate it. A classic “drop the hanky” move that can help keep a conversation going, and make it one-on-one, is asking a man you’re interested in if he minds walking you to the train station or back to where you’ve parked your car. “Giving a man a purpose or role helps us to feel needed, which makes us feel good!” one man affirmed.

Another said, “Seeking our advice and accepting our help makes us feel respected and like you care about our opinion and ideas. This might make me think you care about me too.”

“If I invite a woman out for a coffee or meal, if she doesn’t offer to pay half of the bill, I know it was most likely a date,” one man told me. “If she does offer, it makes me feel that she’s indicating it was just a friendly meet-up, especially if I was the one who invited her.” 

Closing Thoughts

Let’s make our Victorian ancestors proud by continuing the practice of “dropping the hanky” in modern-appropriate ways. No, unfortunately we don’t have an exact equivalent (an iPhone drop would be risky!), but creating environments where we can encourage, reciprocate, and drop hints about our desires and hopes for a man’s intentions are all good ways to help move things forward. 

Remember, women are the gatekeepers of giving men permission to pursue us, so let’s make this single season, however long or short it is, one full of radiance, grace, and most importantly, confidence and fun. 

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