I also pulled from these related reddit threads to keep it spicy. 

"The next day, I tried again. Her older brother opened the door, said she was washing her hair, and told me to take a hike. I tried again the next day, and her grandmother answered. She didn’t speak English and gave me the evil eye before closing the door. The next day, I took a shower, put on brand new clothes I got for school starting the next month, crossed my fingers, and knocked on the door.

Her mom answered the door, said she liked my shirt, giggled, and asked why I didn’t take the price tag off, but invited me in for lemonade and to say hello to her daughter. Her mom said she admired my persistence, that I was the cleanest boy she ever met, and 'You smell like Palmolive soap!'

That girl and I would go on to watch lots of movies together."

"So the biggest difference is you had to go into the actual world to meet a prospective date — they weren't on an electronic device. And I'm talking to the gay world."

"There were very specific places you went on dates with a regular boyfriend, usually the movie theater. They would start a new movie every Friday. There were lots of parties at people’s houses and your regular gang always came. Everyone took turns either having a party in the garage or basement of their house with the record player going and everyone dancing and laughing. It was very fun because it was pretty much everyone in your age group in town invited. This was dating in the late '60s for me."

"I don’t think that sex between coworkers happens nearly as much as it did in the '80s. However, I may just be noticing that I have aged out of the group that engages in this behavior..." 

"Today, dating a coworker is considered risky. Many of my coworkers have a 'no dating coworkers' policy. I know I do." 

"For the check amount, it really depended where you lived. I was in Silicon Valley at the time, which was heavily populated by single, lonely, horny male engineers — the fee started $2,000. The ladies were in real demand so they often were charged $800 or less. The opposite happened in the Castro District of San Francisco. Straight men were in short supply, so the ladies were paying premium prices and the guys were getting good deals.

My sister was so impressed with my success that she joined Great Expectations in Denver and met a guy who was driving from Breckenridge, two hours away, for each of their dates. She moved in with him and they married two years later. 

She passed away about five years ago, but he and I are still good friends."

"I know for some people it worked out, but it didn't for me." 

"Those personal ads could be pretty funny, unintentionally so. There were as many as a full page of them. 'Christian gun owner seeks same. Likes movies, walks on the beach.' That sort of thing. Online finished them off: dating services, social media, Craigslist, and so on." —u/Tall_Mickey

"When you'd meet someone online back in the '80s and '90s, it was likely through a shared interest group, so you automatically had something in common. And the amount of media to consume was smaller. Getting a picture digitized or scanned was not something everyone could do, so seeing a physical representation of them was also exceedingly rare.

My late wife and I met online in 1992 through a multi-user server (specifically, TinyMUSH). We knew several other couples who met that way. In all but one case that I can recall, we all lived hundreds to thousands of miles apart. Some were even on different continents. We, for instance, lived roughly 1,500 miles apart."

Note: Responses have been edited for length/clarity.