Chronicling the History of Yearning with Long Lost Personals

It’s an age-old fantasy: you gaze across a crowded room, lock eyes with an attractive stranger, and fall in love at first sight. Alas, things don’t always work out this way. This is why, historically, so many romantic hopefuls have chosen to take matters into their own hands. 

In the smartphone age, this typically means hopping on a dating app. However, decades ago, star-crossed yearners didn’t have that luxury. Instead, they placed personal ads in their local newspapers, condensing their hopes and dreams into carefully worded lines of printed ink.

Curious to see how the dating and hook-up scenes have changed across eras and how they’ve stayed the same? Check out the Instagram account @longlostpersonals. 

Every day, the page’s creator, a Chicago man named Dan who prefers to remain behind the scenes, posts another personal ad taken from the newspapers of yore. He largely draws from the 20th century but sometimes he travels even further back in time. Some of the ads feature made-up portraits; others paint pictures with text alone. All of their subjects long to present themselves as worthy of attention, achieve meaningful connection (whether through a relationship or a kinky sexual encounter), and, above all, shout into the void. 

Dan seems to understand that his page is so compelling because it highlights the universal nature of these desires. “You will find love, in time,” its bio reads.

Recently, I had the chance to chat with Dan about his archival project. Our conversation covered everything from the genesis of the account and the personal ad as a literary genre to the most memorable character he’s come across (a fedora-clad swindler who was charged with fraud). 

Photo: Emmanuel Codden via Pexels

Juicy Pink Box: First and foremost, what inspired you to start documenting personal ads?

Long Lost Personals: I have always been a collector of things. First, it was baseball cards and comic books, then Star Wars stuff. Eventually, I got rid of all the juvenile stuff and settled into records, LPs, antiques, and ephemera. My dealings in collecting often brought me to the classified sections of newspapers. Every Thursday night, right after I got my driver’s license, I’d grab the newspaper, circle all the garage sales in certain areas, make a little route for myself on MapQuest, and then go sale to sale. And I would buy and sell things in classified ads, both online and in the paper. 

I started selling stuff online when I was 11 or 12 years old. That was predating eBay; I used AOL classifieds. The personal ads were always right next to whatever I was doing and I thought it was so interesting and fun to read these people pouring themselves into one paragraph to try to best describe themselves. 

So [the personal ad] has been in the back of my mind… but what gave me the idea to start the page is, in 2008, a friend of mine who used to be a librarian at the Newberry Library, a private research library here in Chicago. [When she took me there, I saw] a newspaper called “The Matrimonial News and Special Advertiser.” It was a Chicago publication that was published in 1877, and it was all personal ads. 

I thought it was endlessly entertaining to hear people describe themselves and what they’re looking for in this flowery, old-timey language. So I made her make a copy for me, which I took home. When the pandemic started, I came across it while cleaning out my house, and I got to thinking, “Wow, I wonder if I could find more of this stuff?” I went online, and I found another issue from 1872, and then I started finding stuff from other eras—‘20s, ‘30s, ‘40s, ‘50s—and then I started finding more current stuff with [swingers’ ads], and it turned into a whole collection. I decided the best way to share it would be this Instagram page. 

Juicy Pink Box: Where do you find the ads you post on your page? Are there certain websites, libraries, archives, or other resources you rely upon? 

Long Lost Personals: I personally own probably about 99 percent of what I post. I’m not searching online to find this stuff; I am paging through magazines and newspapers. I order from online bookstores. eBay is a good source, Etsy sometimes, Facebook marketplace, Craigslist. Sometimes, I find stuff in person—if I go to an antique mall, I usually come across at least one stall that has some ephemera, and I’ll get stuff there. Garage sales, estate sales.

Photo: Digital Buggu via Pexels

Juicy Pink Box: Has anyone featured in any of the ads ever reached out to you? If so, what stories did they share?

Long Lost Personals: No one has ever reached out and said, “Hey, that’s my ad.” I’m holding out hope—as I grow more visible and as I put more content up, it’s got to happen. I [sometimes post from] a collection of seven or eight books—this was a 1980s phenomenon—that are full profiles of bachelors and bachelorettes. A lot of the people in these books are well-known figures, so you can find them pretty easily. I did have someone reach out and say, “Hey, I know one of these people moderately well.”

There’s another page similar to what I do—Q4Q: Queer Personals. The person who runs that page, Haley, is an archivist, and they archive queer personal ads. Sometimes, I’ll repost their stuff, especially on my stories. One time, an ad was put up—from the ‘80s, I think—it was a guy who was in the rock and roll scene, and he was looking for punk rock boys wearing leather wading boots, something super specific. And one of my followers reached out to me and said, “Holy shit, I think I know who that is. There’s this guy who’s in all these Facebook groups that looks for exactly this. I’m gonna reach out to him.” The guy was like, “Yup, that’s me!” 

So [the personal ad] has been in the back of my mind… but what gave me the idea to start the page is, in 2008, a friend of mine who used to be a librarian at the Newberry Library, a private research library here in Chicago. [When she took me there, I saw] a newspaper called “The Matrimonial News and Special Advertiser.” It was a Chicago publication that was published in 1877, and it was all personal ads. 

The only other story I have is this: in Minneapolis, where I grew up, the local free paper is called City Pages. I had an ad placed looking for something else in Minneapolis. This guy responded [and I went to his house, but I wasn’t interested in any of his stuff]. 

He was like, “Oh, yeah, what are you interested in?” I was like, “It’s kind of weird, but I collect old personal ads.” 

He was like, “Oh, really? That’s funny. I don’t have any, but I used to place them all the time.” 

I was like, “When?” 

This guy was, like, 73. He was like, “Back in the ’70s… any time I got horny, I would just throw an ad in the City Pages. You would not believe how well I did.” And he told me some pretty lurid sex stories that I was not expecting coming from this random 73-year-old man that I had just met.

Photo: 幻影 多媒体 Prado via Pexels

Juicy Pink Box: Have you ever tried reaching out to any of the people yourself to see, “Does this number still work?” or “What’s this person’s deal?”

Long Lost Personals: I never have. Occasionally, I’ll Google people. Sometimes, my followers do, and they’ll be like, “Check this guy out.” I posted this guy… His picture makes him look like an aging Indiana Jones; he has a little fedora on. He mentions one of his interests as “searching through lost mines.” 

But if you Google him, [you’ll find] a case brought against him in the 1940s. He was getting people to invest in these lost mines, claiming he found lost mines full of gold and diamonds, and they’d give him all this money, and he turned out to be a total fraud.

Another one was this magician from the early ’70s. I found two different ads from him and, through a combination of Googling him myself and some research that my followers did, discovered that this guy was involved in a giant pedophilia ring in Michigan. It’s definitely unfortunate. His ad went from being funny and charming to “Oh, this is disgusting.”

Juicy Pink Box: You mentioned that you saw two different ads from him. Is it common to see recurring characters?

Long Lost Personals: Absolutely. Sometimes, I’ll see the same people in two different publications. Other times, I’ll see people in the same publication ten years apart. I can tell that some people are lying about their ages because I’ll get a woman who says she’s 48 in a 1972 ad and also in a 1975 ad.

Photo: Aline Viana Prado via Pexels

Juicy Pink Box: You post about all sorts of connections, romantic and otherwise. Why do you choose to share posts about friendship as well?

Long Lost Personals: The purpose of my page is… I think it ignites some curiosity in you when you see somebody reaching out for human connection, whether that is somebody seeking love and marriage or someone looking for friendship. It could be that a person is hoping for an arrangement—because some of my posts are from mail-order-bride catalogs where some people might be seeking genuine love, but the purpose of some of the ads was really just to get US citizenship. 

I have all these pen pal ads; some of them are kids. I actually just got some children’s magazines from the 1940s with kids looking for pen pals in there. They’re very cute. It’s the idea of connection. 

Some people are strictly seeking sex or kink arrangements or a third in their swinging relationship. And some of these ads… might be from sex workers or might be scams or other types of money-making opportunities. 

You never really know what somebody’s angle is. Ultimately, I leave it to the people looking at it to judge the nature of the ad and what it really is. 

Juicy Pink Box: I’m sure you have a very broad audience, but I would consider myself a Millennial/Gen Z cusper, and a lot of my friends who follow the page are as well. What about the page do you think appeals to younger generations? 

Long Lost Personals: My page at the moment spans from 1850 to 2000. That in itself tells you that there is something universal and timeless about the hunt for connection. The current generation is no different than any generation before them. We’re all looking for connection. Obviously we’re looking for it in very different ways. 

Photo: cottonbro studio via Pexels

I’ve never placed a personal ad, but I’ve responded to some online personal ads back in the day. I responded to many old classified ads. But I’ve also been on dating apps, so I’ve kind of been on each side. 

As far as younger people go, I think they find it a little curious. There’s something about seeing people from the past looking for connection. You instinctively want to know what happened to the person; you want to know the story. Because most of these publications have little, if any, identifying information. Even in the age of information when you can look anything up, we’ll probably never be able to find out what happened to these people.  

It’ll be in your mind as a question mark. And I love that sense of the unknown. We don’t have a lot of that these days. 

Juicy Pink Box: I was listening to your interview with Vintage Annals Archive, and you note in that interview that you don’t post ads past the year 2000, partially because you don’t want to veer into the territory of Tinder screenshots. Would you say it’s fair to characterize dating app profiles or social media pages as the modern-day equivalent to personal ads, or would that somehow be blasphemous to the form of the personal ad? Where do they diverge?

Long Lost Personals: Absolutely. I’m not on dating apps currently, but I’ve probably been on dating apps for a period of two years, if you put it all together. 

In some ways it’s a shortcut, and people are lazy about it, but people were lazy about personals, too. What you see on my page—I post the interesting ones. There are so many that you read, and it’s like, “Wow, I’ve read the same one so many times before.” But some people put a lot of effort into their photos and their descriptions. 

I think that you can put a lot of thought into a dating profile, just like a personal ad. Ultimately, the goal is the same. You want to attract a type of person. And if you’re trying to attract someone who has a witty, creative brain, you’re going to want to put some of that energy into your profile. 

I do think it’s the modern-day equivalent, [although] some things have probably been lost. Obviously, there are a few differences. One of them is [that the apps function as a gatekeeper]. If I swipe on someone and they swipe on me, within the confines of most dating apps, we have the ability to initiate communication, but if we don’t mutually like each other, I have no way of communicating with them, and they have no way of communicating with me. There’s a sense of safety in that. 

But a lot of people posted their contact info when taking out personal ads. Your mailbox, or your P.O. Box, could be filled with letters from anybody—so mail day must have been incredibly interesting. 

Photo: jhenning via Pixabay

Juicy Pink Box: Do you think there’s something about the print medium in particular that lends personal ads their magic or shapes the content differently than writing on a phone shapes the content of a Tinder profile, per se?

Long Lost Personals: I do. Back then, when things were in print, you had to put in effort. To place an ad, you had to get a copy of the publication, go through the trouble of finding the page that tells you the information on how to place an ad, fill out an ad, place a stamp on an envelope, and mail it in—and then you had to pay for it. You would have been paying by the line or by the word in most cases. And that’s quite a lot of effort when you think about it. To that end, people were probably putting a bit more effort into what they were writing. 

Nowadays, it takes almost no effort to put up a Tinder profile. It doesn’t cost any money unless you want to subscribe to Premium or whatever they call it.

Juicy Pink Box: You touched on this a bit, but as a writer, it’s easy to see the personal ad as almost adjacent to a poem comprised of carefully chosen words intended to convey multitudes. What about the personal ad as a literary genre interests you on the thematic level and also the formalistic or sentence level?

Long Lost Personals: There are definitely some trends there. First of all, I have seen personal ads literally written in rhyme or meter. I had one that was written in pig Latin, which was insufferably annoying. (Laughs) 

If you’re swiping on a dating app, people start to copy each other, especially among the less creative of us. I was a little late to the game; I think I first got on a dating app five years ago. It was pretty well-worn territory at that point. I would start to see words and phrases, and the first time I saw them, I’d be like, “That’s creative,” and the hundredth time, I’d be like, “Okay, people are just copying each other.” 

I’ve seen the word “‘enthusiast” a million times. (Laughs) With the ads, people do start to copy each other and sound alike. You start to see a lot of phrases in common, such as “with a view to marriage,” “object: matrimony,” “object: fun,” and “here is a girl of 18 summers.” 

The major demarcation line in personal ads is the sexual revolution. I don’t have anything that is lurid or blue before 1965. Once you get into the mid to late ‘60s, that’s when the first swinger publications start to come up. The first ones are a free-for-all because people haven’t really been able to place this stuff before. The language is not uniform because they have to think for themselves… and this has never been done. 

And then when you get five, ten years in, the language gets very uniform because the people who are placing the ads have read so many that the verbiage gets stuck in their heads. 

When free weekly city papers started coming out—such as the Village Voice, the Seattle Stranger, the Chicago Reader, and the LA Weekly—people are placing a lot more print ads without pictures and it gets creative again. People realize, “I’m not putting a picture in here. I have to stand out in a sea of text.” 

Photo: Aromateec via Unsplash

Juicy Pink Box: As apps and websites emerge as this new romantic and sexual marketplace, do you think it’s become easier for romantic hopefuls to find meaningful connections, or are we somehow lonelier today even with all these means to connect?

Long Lost Personals: That’s a hard question to ask when you put the ads and apps and stuff in a vacuum, because there are a lot of other factors at play as it relates to loneliness and technology. 

I think the main difference is, again, the effort. When you meet someone that’s worthwhile [through a personal ad], I think you’re willing to put a little more effort in because it’s been a lot of work to connect with that person. You’re willing to give that person a little more room, be a little more understanding. 

Nowadays, people are so much more disposable. It’s so easy to look for the next best thing when you’re swiping on a dating app.

Photo: Remi Clinton via Unsplash

Juicy Pink Box: Last but not least, I noticed the page’s bio reads, “You will find love in time.” Do you see Long Lost Personals as a channeling of collective hope? Is there a certain ethos or message that you hope to convey to your followers through posting these ads?

Long Lost Personals: Yeah, I like that. I’m gonna grab one of my publications here… This magazine ran from the ‘30s into the ‘50s or ‘60s. When I put, “You will find love in time,” I was kind of channeling this energy. 

[Dan reads from the publication, which features a variety of platitudes on its cover page—such as “When a man is no longer faithful to his purpose, destiny deserts him” and “Infinitely fast is the flight of time, as they who look back may see.”]

I look at the page as a lens to the past. I like the idea of, Maybe you’ll find a connection with this person you’ll never meet or see who could possibly be dead. This is ephemera, and the meaning of ephemera is “something that you’re not really meant to keep.” It’s something that will be here for a time, and then it will be gone one day. 

Whether you’re looking at an ad from 1950 or 1970 or 1885, it’s a window into a person who was looking for love—or some kind of connection—at some time, and you don’t really know whatever happened to them, but you get to have this weird little interaction with them.