Other people (including my husband) had a much longer, more frustrating time trying to make dating-through-personals work

Off topic to the Askme but I know two couples who met via the Boston Phoenix personal ad section – one of the couples had their ad framed and hung it in their guest bathroom.

A GLOBALLY SEASONED EARLY 70S SoCal media artist, financially stable with abundant Weltschmerz, seeks to meet an erudite, genial, and independent woman 60–75 who remains curious about the wonders that life still holds. My pronouns are ars gratia artis. Let’s be pen pals starting with a short Bio and see, as photographers would say “what develops.”

My now-husband and I met via a personal ad that I placed in the local alternative newspaper. I had read the ads of women in my age range and wrote one that was designed to stand out and give as much info about my personality in a very short written description.

Placing an ad with the newspaper was free, but leaving voicemail to respond to an ad was not. There was also some sort of system where I recorded answers to questions about my age, interests, etc over the phone, and people could somehow browse those responses without reading the ad.