In the early 90s I had a roommate who used the printed personals for dating for a while

I met up with three women I think. Each time we'd have at least one, probably more, conversations before agreeing to meet up somewhere in central London for dinner or coffee.

Note that at that point, neither of you knew what the other person looked like. There were no camera phones, not a lot of digital cameras, etc.

I guess she had a really sexy phone voice because they spent a solid couple of weeks having intense phone sex every night (tying up our single phone line, of course), and then one night the phone sex was so good he headed over to see her

Two dates were. not awful, but things clearly weren't going to go any further for either side. The other one, we became friends for a while after.

Fwiw, the LRB ended its personal ads in 2010. It still has a small handful each issue but they're quite conventional compared to the pre-2010 ones. posted by fabius at 5:35 AM on [1 favorite]

My memory is that there was a much closer balance in numbers between men seeking women and women seeking men, unlike apparently the situation on dating apps now

In my experience, ads were classified as Men Seeking Women, Women Seeking Men, Men Seeking Men, and Women Seeking Women. There might have been one for people seeking friends, but I'm not sure (the "friends with benefits" thing didn't really exist).

Like others mentioned, there was also the Missed Connections section, which I always read and was always disappointed that no one was ever describing me.

He placed an ad in the local free alternative weekly paper and also responded to other people's ads. It was via voicemail, so you got a PIN and could call in to see if anyone had left you a message (so much miksi itäeurooppalaiset ja venäläiset naiset ovat kauniimpia kuin amerikkalaiset tai englantilaiset excitement if there were messages, and much disappointment when there were not). Then it would move to phone calls, and from there maybe a date in person. He stopped using it after he got catfished. Unfortunately she was not as she had advertised, much older, very different physically, and it was overall such an unpleasant experience for him that he quit the personals dating entirely and went back to hoping to meet someone in person.

(But, that also might have been with a bunch of fake ads to pull in men and thereby earning the paper money from the voicemail fees.) posted by Dip Flash at 6:03 AM on [1 favorite]

Back in the 1980s, I worked in an office in Soho, then still a slightly rakish area of London. There was a tiny kiosk next to the door of our offices which sold cigarettes, sweets and other such items. What I hadn't realised was that this guy also operated the kiosk as a discrete forwarding service for anyone not wishing to receive questionable letters at their home address.

One of my jobs was to open the the stack of hard copy post our office got each morning. If something was in the pile I'd been given, I automatically assumed it was for us and sliced it open without even glancing at the address.

One envelope on this particular day disgorged a dozen or so explicit photographs of a middle-aged couple shagging, together with a covering letter explaining they'd seen the intended recipients' personal ad in a Readers' Wives style porn mag, and looked forward to receiving their own pics in return. Retrieving the envelope, I realised it should have gone to box whatever-it-was in the kiosk downstairs - which I guess was one of the ways amateur porn operated in those ancient times.