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This IG Page Shares The Most Hilarious "Looking For Love" Ads, And Here Are The 50 Best
CuriositiesAUG 7, 2025

This IG Page Shares The Most Hilarious "Looking For Love" Ads, And Here Are The 50 Best

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Today, people look for love on dating apps. In 2023, at least 30% of adults in America said they've used dating apps at least once. But back in the day, you'd have to take out a personal ad in the local paper if you wanted to find love or reach out to a missed connection.
Also called lonely hearts ads, these short messages would often be quirky, romantic, and witty. But they could also be direct, morally questionable, and contain a whiff of casual sexism. Thanks to the Instagram page Long Lost Personals, today we get to see what folks from the '50s might've put in their Tinder bios if they had a chance.
So, what are you waiting for? Scroll down and maybe you'll get some inspiration for your next conversation starter from these vintage Don Juans and Femme Fatales!
More info: Instagram

#1

Vintage personals ad describing an inattentive, plump female who is a compulsive reader and good cook.
1983. At least she got around to placing this ad.
35points

#2

Vintage personals ad titled Ex-Nun Starved for Romance seeking companionship and marriage-minded man.
1967. For your Sunday morning This is the closest I could find to the Sister Act soundtrack version. Now I feel like watching Sister Act.
35points

#3

Personal ad expressing love for dog and Mozart, seeking slim dark-haired scholarly men for romance connection.
Late 1980s-ish. A couple more personals from the bedsheets! I found an awesome set of vintage bedsheets with personal ads from New York magazine printed on them. Unfortunately they are twin size, so I can’t sleep in them unless I get a twin bed.
28points

The modern newspaper came out around 1690, and it only took a few years for horny folks to start looking for hot singles in their area. At the beginning of the 18th century, matrimonial agencies were a very serious thing. Men would pay these agencies to post ads in the newspaper on their behalf to recruit a good wife for them.

There was little pride in using this service. Unmarried men and women past the age of 21 would be shamed to no end by society, and if your friends found out you used the services of a matrimonial agency, it would signal your own inadequacies as a wanted suitor.

By the early 20th century, personal ads were much more mainstream. There was less pressure and expectations, and some people really were just looking for pen pals or friends.

#4

Tattooed and pierced vampire in Detroit seeks local Gothic lover for unusual and bizarre romantic connection.
1995. Detroit vampires always trying to glamour you with their long letters.
27points

#5

Vintage personal ad from a 22-year-old woman seeking meaningful romance and connection beyond appearances.
1967. An early sapiosexual.
27points

#6

Personal ad from a petite lady nurse seeking romance with an Italian or Jewish gentleman for activities and lasting relationship.
1976. Finally, someone who sees the virtue in vice.
27points

Until around the 1960s, personal ads were used mostly by "lonely soldiers" and people looking for pen pals. According to history lecturer at the University of Nottingham, UK, H.G. C***s, it still wasn't as widely accepted. "At that time, advertising for pals or for lonely soldiers was fashionable and contemporary," he explained. "Something done by those who were, as they put it in their ads, 'bohemian and unconventional.'"

For many years (and perhaps until today, even), people associated personal ads with suspicious and seedy folk. "At least that is what the police tended to think, and they only stopped prosecuting lonely hearts ads in the late 1960s — until then, they often thought that they were mainly placed by [adult workers] and gay men," C***s says. 

#7

Vintage personals ad from a small Montana town seeking connection and romance, featuring a pierced nose detail.
1995. The whole town freaked, even the horse.
26points

#8

Personal ad from a shy 31-year-old virgin seeking romance, highlighting timeless themes in personals columns.
1981. Time to face your fears.
26points

#9

Personal ad describing an articulate, witty woman seeking emotional connection and friendship in romance personals.
1984. I am not a dream boy.
25points

Today, some people equate internet dating sites to the personal ads column. They attract people who have failed to court a partner in the traditional way and are often used by older people. People over 30 still prefer dating apps or meeting people the old-fashioned way.

When asked whether personal dating ads just boil down to "Loser seeking Winner", C***s has a more nuanced view. "I think those opinions are really those of younger people, [such as] those under 30 who see no need for Internet dating. Or of married people."

#10

Vintage personals ad titled Pink Pig Girl recounting a heartfelt encounter and offering to return a lost doll.
2004. Fun to throw a missed connection into the mix every now and then.
24points

#11

Personal ad seeking woman to marry German friend, highlighting themes of romance and connection in vintage personals column.
1984. From Bay Windows, New England’s largest gay and lesbian newspaper.
24points

#12

Black and white photo of a man in a bow tie with a personals ad seeking diabetic singles for a nudist colony.
1976. According to Wikipedia, the first insulin pump was manufactured two years before this ad, in 1974. I wonder if this nudist colony ever got off the ground.
24points

We might think that personal dating ads are a thing of the past. You might listen to "The Piña Colada Song" by Rupert Holmes and think: "This is so '70s! Who puts an ad for a hookup in a newspaper?!?" Surprisingly, these types of ads might actually be making a comeback. Lately, experts have noticed a trend where people are craving a slower type of dating – one that Hinge, Tinder, or Bumble can't really provide.

#13

Vintage personals ad seeking hypnotic romance from an aggressive woman with knowledge of hypnosis and strong beliefs.
1974. You’re getting sleepy. Very sleepy.
22points

#14

Vintage personals ad from a girl in a wheelchair seeking connection, illustrating timeless themes in romance ads.
1972. Beep beep. This is what the horn plays.
20points

#15

Vintage personals ad with a poetic message about life and romance, featuring a phone number for contact.
1966. I knew there was an answer. RIP Brian, one of the great American composers.
19points

In 2019, several pages dedicated to posting people's personal dating ads began making the rounds on Instagram. One LGBTQIA+ personal ads page even had 60k followers at that time. A similar page still exists today on Twitter and Bluesky – it's the Red Yenta for socialists. The QPOC Personals for queer and trans people of color was going strong until COVID hit, but is still a testament that we're craving another kind of dating experience.

#16

Handwritten personals ad titled very lonely girl describing a woman seeking romance with simple joys and physical details.
1968. For those who are lonely.
18points

#17

Vintage personals ad featuring a woman seeking a submissive spouse and patron of the arts, highlighting romance themes.
Date unknown. She’s just after your Dalmatians.
18points

#18

Black and white vintage personals ad featuring a man seeking single girls for fun and romance, reflecting classic personals.
1972. I can dig it.
18points

Cincinnati magazine CityBeat also tried bringing back looking for love through personal ads for Valentine's Day 2025. Years ago, the publication ran a section called "CINgles." As co-founder of the magazine Dan Bockwrath explains, they "were kind of the original social media before social media went digital."

"I think there was some authenticity to what it is that we did," he went on. "I think people were very genuinely interested in using the platform for its intended purpose."

#19

Vintage personals ad featuring a young person from Sandusky Ohio seeking boy and girl pals aged 14 and up.
1965. These are from a teen beat magazine from 1965 where adolescents and young adults are seeking pen pals (and some flirtation, from the looks of it). We are wishing Joy the best of luck in her collecting endeavors.
17points

#20

Vintage personals ad text reading a playful birthday message referencing biting a neck, illustrating romance and personal ads.
1972. Time to go see Nosferatu.
17points
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