Does Chivalry Still Work? My Failed Journey as a Perfect Gentleman.

illustration of chivalry dating
Jason Hoffman/Thrillist

Let's be real: the modern dating landscape is a mess. If you can even find a remotely compatible romantic prospect without developing carpal tunnel from excessive swiping, there’s an endless number of nightmarish scenarios waiting for you: catfishing, turning into someone's WELP, or just being flat-out ghosted.

I know the horrors all too well. After a long-term relationship ended last fall, I was thrust back into the role of a 21st-century single man. I dove unprepared into the belly of the beast. Said belly was filled with unanswered Tinder messages, awkward bar-side conversations, and a constant, nagging fear of being stranded indefinitely in that sketchy purgatory.  

Melodrama aside, I needed to shake things up.

I've always been romantic. It's the result of a one-two developmental punch: having a "Midwestern nice" upbringing, and being heavily influenced by a Southern Baptist grandmother who kept a discerning eye on my manners. If only some old-school courtship techniques would come back into fashion so I could actually play to my strengths.

Ignoring the repressive, patriarchal system that birthed them, antiquated dating practices would undoubtedly civilize the modern dating world. Why shouldn’t some of the more genteel conventions of courtship work today? Everyone loves the classics, right? The more I thought about it, the better the idea seemed. So I got back into the dating game and went after women like it was 1799.  

old school dating techniques awkward date
Everett Collection/Shutterstock

First thing's first: what 300-year-old dating techniques to try?

The first step on my quest was to choose from dozens of old-school dating behaviors. Obviously, some of the more elaborate classic moves were out of reach. I'm not really in the position to roll up to some lucky lady’s apartment in a horse-drawn carriage decked out in a coat and tails; nor will it do me much good in New York City to lurk on a street corner asking women if I can walk them home.

I settled on four dating strategies: classic old-fashioned manners, calling instead of texting, handing out calling cards, and bringing a chaperone. One of these tactics was bound to work. There were some necessary evils of the modern age (read: Tinder and Bumble) that I had to retain in order to connect with women in the first place. And I had to keep up most standard modern conventions like the constant texting loop to which we all fall prey.

Emphasizing etiquette

I started things slow on my next Bumble date by simply emphasizing the manners I'd been taught growing up. I held the door for her when we walked inside, pulled out her barstool for her, helped her with her jacket, stood up when she rose to use the bathroom, and covered the bill without any awkward pauses. It was a nice evening, but hardly a huge deviation from the norm. I'd have to up the ante.

I insisted on walking my date from the bar to her subway stop; and when she visibly pulled her jacket tighter, I took my coat off and draped it over her shoulders. She was clearly surprised, and immediately tried to dissuade me as I shoved my now-freezing hands into my armpits. I insisted she keep it until we reached her stop. When we reached the glow and steamy air of the underground station, I took my jacket back, kissed her hand, and we parted ways.

Long story short, I got ghosted and haven't heard from her since.

a man on the phone chivalry dating

The call

In need of a plan B, I returned to Bumble. I had been chatting with a woman on the site who I had genuine interest in, so I was a little gun-shy to try out these new/old moves on her. But this was no time to hold back! I needed to channel the generations of polite and romantic men from eras past. A few days after exchanging numbers and without warning, I hyped myself up, picked up the phone, and gave her a call.

The phone rang a few times while I half-prayed for her not to answer. Her "Hello?" came packaged in a small, confused voice. Our conversation was short: I asked her out for a specific night, she said she was busy, I fumbled through other suggestions, she told me she was cooking dinner, and asked to call me back.

While I did get a text later that night -- and though we have exchanged messages since then -- I still haven't met her. I'm willing to give her the benefit of the doubt and assume this is a scheduling conflict; not her being creeped out by the phone call.   

Calling cards

I clearly needed to leave the app game behind and try for a totally tech-free, old-fashioned experience. So, I met up with my buddy Ian in his neighborhood to hit a few of his favorite bars in classic single guy-and-wingman fashion.

After chivalrously coming to the rescue of a girl under assault from a dude with the absolute opposite approach to mine (Sidenote: it is never OK for a douchebag bro to just start grinding up on a woman in lieu of saying hello), I was able to bust out an old standard for the first time: the calling card.

My wallet was filled with them, ready to be handed to any ladies who caught my eye. When I handed the recently liberated damsel the first one, all I got was a weird look. When I explained that the obviously un-business card was just my way of telling her I was interested, I got some not-so-encouraging feedback: "Well, that's a nonstarter."

I tried the calling-card trick on other women throughout the night. The responses were consistent: "Sketchy as shit," "Thank you, but I'm not interested," "This must be an age thing," and "Depends on the person, and it’s not you." My personal favorite came from a 30-year-old stunner from Seattle who was, unfortunately, just in town for the night visiting a friend.

"If you're handing me a card," she said, "it's going to have to give details of your full sexual history."

The chaperone

After the calling cards yielded no results, I had one last method to try. I set up a weeknight date with a girl I had gone out with a few times before... and then double-checked that my good friend Michelle would be able to make it as well. Yup, we needed a chaperone.

This was to be sure that things wouldn’t move too quickly so I could live up to my romantic aims without succumbing to my baser nature. And yes, there are still communities in the US that do this for every date until marriage.

Amanda, the girl I was meeting, didn’t know the date would be monitored. When she walked into the bar, she saw Michelle but didn't say anything until I introduced her as "our chaperone for the evening." The girls exchanged pleasantries, and we sat awkwardly at the end of a long table as I limped through a conversation with Amanda while Michelle silently observed us.

After about two minutes, I’m ashamed to say that the awkwardness was too much for me. I fessed up and told Amanda about the experiment (much to Michelle's chagrin, sorry dude) and we went on to have an otherwise normal conversation between three friends. Amanda later told me that she knew something was weird, but wasn’t quite sure what to think. How would she have reacted if she hadn't known me already? We'll never know, because I'm not exactly planning on pulling that stunt on anyone ever again.

man texting on phone dating apps

Dating rituals have moved past old-school dating habits

Other than when I was using the more outlandish, outdated methods like the chaperone and calling cards, the ways we interact during the courtship process don't seem to have changed all that much. What has shifted radically are the platforms where we meet. Chivalry isn't totally dead -- it's just gone digital.

Having a virtual layer between people who are interacting romantically stunts the emotional impact and stakes of things. We’re already used to engaging with our phones around the clock, so texting a new romantic acquaintance or meeting someone on an app takes place within a totally familiar context. When I was handing out calling cards to women I had just met, and especially when I made the phone call to a girl I was very interested in, I was more nervous than I can remember being in a long time. But we should be a little scared and excited sometimes! Is dating really worth it if it's so effortless that you barely feel anything at all?

I won't go around handing out calling cards or go out chaperoned again anytime soon -- but I will keep my manners in check and look to find new ways to get out of my comfort zone for more actual, interpersonal engagement within the dating world. And if you're wondering whether any of this ended with any type of 21st-century "payoff," you can let your imagination run wild. After all, a chivalrous gentleman never kisses and tells.

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Brett Williams is a writer in New York City. He’s ready to take a break from dating for a while -- unless he has a chance to try the courtship techniques of the future, that is.