Trying to Find Love on These Streets? Better Have a Big Roll of Tape.

Alex Miller, a software engineer living in Brooklyn, needed a date for his brother’s wedding. Being a digitally savvy millennial, he came up with a plan to attract a potential plus-one for the ceremony: He printed about 20 personal ads with his contact information and posted them around his neighborhood.

Mr. Miller, 32, was surprised to see people actually messaging him with inquiries. There were some who treated the search like “The Bachelor,” with questions about the “competition” and whether Mr. Miller would be “giving out roses.” Others reached out on behalf of friends they felt would be a perfect match for him.

“I did ask someone, ‘OK, I’d like to see a reference,’ and they had a friend of theirs send me a text like, ‘Hey, my friend is such a great person and I think she would be great to date,’” Mr. Miller said in an interview five days before the wedding. “So that was a fun thing to be happening in my life.”

Long before people were swiping left and dating online, hopeful singles were buying space in their local newspapers to advertise themselves as potential lovers. Such personal ads began appearing in newspapers as early as the 1700s.

By the mid-20th century, the trend had exploded across different publications, including The Village Voice, New York magazine and Singles News, as a novel alternative to bars and clubs for people eager to find a match or just a fling.

With dating-app burnout practically the default mode for digitally active singles (all that swiping! all those paid subscriptions!), is there room today for that kind of old-school approach?

Back in December, around the time his younger brother sent out invitations for his April wedding, Mr. Miller wasn’t sure whom to take as his date. While discussing his quandary with his sister, the idea of a personal ad popped into his head.

“Lately I’ve been spending a lot of time on the dating apps, and they’re good in some ways but not so good in other ways,” he said. “Around the time that I made this flier, I was feeling like I wasn’t enjoying the dynamics of being on these apps and feeling the stress or anxiety of responding to different artificial-seeming conversations.”

Mr. Miller’s dating life isn’t so unusual, he said. It’s a mix of ups and downs, with a lot of time spent on Hinge. “Sometimes it can be a challenge, so it was nice to experience a different way to meet people,” he said.

His flier featured a photo collage showcasing him happily engaged in a variety of pastimes, including playing the keyboard, indoor rock climbing and reading a book on the beach. He screened would-be dates with just three questions: “Do you like dancing? Do you like pleasing Jewish grandmas? Do you want to go to a wedding in April 2023?” For those who could answer yes to all three, at the bottom of the page were tearaway strips printed with a Google Voice phone number he created to avoid any potential trolls having access to his personal line.

He has received at least 20 messages since December, he said. Among the respondents were a couple looking to be a plus-two to his brother’s wedding and a Texas woman who got his number from a friend in New York.

This month, one flier seen freshly posted in Carroll Gardens on a Tuesday was missing all of its phone-number strips by Friday.

“That’s pretty funny, because in today’s day and age, there’s no need to rip off the flier at all: You can just take a photo of it or put it in your phone directly,” Mr. Miller mused. “I guess that’s pretty satisfying, ripping off one of those fliers.”

It could also speak to the excitement of being asked out on a date (sort of) in the middle of your commute: Maybe, just maybe, if a match were made, a number on a scrap of paper would exist as physical evidence of what started it all.

Except in this case, Mr. Miller ended up riding solo at his brother’s wedding, which took place in upstate New York on Saturday, April 15. He said he realized a few days before the wedding that a family function is probably not an ideal setting for a first date.

“I still have to work on my wedding speech, so I don’t want to be off in a corner rehearsing and not knowing if they’re going to be comfortable,” he said.

That doesn’t mean he didn’t get anything out of the experiment. He has made a couple of connections and has other weddings he plans to attend later this year.

“I did start a conversation with one or two people that I’m excited to see,” he said.

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