There were two cases where the chatting led me to decide not to meet up with the person (tip for guys: don’t tell single Moms you’re angry at Bill Clinton because somehow it was his fault that you couldn’t see your daughter because of your failure to pay child support)

One basic question i have is, if you saw a personals ad that piqued your interest, how would you get ahold of the person? would you then talk on the phone for awhile the way people on apps text eachother forever without meeting up? How much did they cost? How often would you re-write them?

If you placed an ad, you got a dedicated voicemail box or a dedicated email address (there was a time when there was Internet but no World Wide Web), and interested parties would either call and leave you a voicemail or send you an email. As the ad-placer, you would then be able to review the emails or voicemails and follow up.

I did such a thing only once; I placed the add, and it was back in 1995 so I do not remember how much it cost. (I think costs varied depending on who owned the ad site; I used one in a free weekly indie newspaper in GГ¶rГјntГјle New York in the 90s.) I followed up on two guys’ voice messages; in both cases, we had an initial conversation and made a date for a second phone call just in case, and then when that second call went well we went on to an in-person date. (With the second guy, our first phone call lasted 2 hours and the second one lasted 4 hours, and then our first date lasted 18 hours and on our second date he saved my life, so I stuck with him quite some time afterward, and by the time we’d broken up and I was ready to date again the online dating apps were kicking off so that was the one time I did the paper personals.) posted by EmpressCallipygos at 8:27 AM on [30 favorites]

My paper also added an option where the person who wrote the ad could leave a voice recording giving more information and you could respond with a voice recording giving your contact information

Yes, I’ve done this. For my local paper, if an ad interested you, you sent a letter to a box number at the paper and the paper forwarded it to the person who wrote the ad. In that letter, you gave your contact information and the person had the option of contacting you or not. People weren’t really using email for this in the late 80s – at least where I was.

The first contact was generally a phone call with some chatting, but was mostly about setting up a meeting. I can’t imagine just chatting on the first phone call without planning to meet.

As I recall, a short ad was free to place and there was no charge for responding. Longer ads cost something, but I don’t remember what. posted by FencingGal at 8:36 AM on [8 favorites]

My grandfather placed one in the NY Review of Books sometime in the 1970s, and described himself as “gumpy eyed” – presumably he also said a few more positive things about himself, because he did succeed in meeting his second wife.

I do know he kept the length pretty short though to keep the cost low – so whatever the precise cost was, it was high enough to make some people want to economize. The NYRB handled the communication – or at least, anyone interested would need to contact a non-personal address/phone number. I don’t believe he ever re-wrote his ad. posted by coffeecat at 8:48 AM on [4 favorites]