One of the best 90's relationship movies ever made is Singles. Seeing how gen'xers go through the motions of dating, meeting people, falling in love, falling out of love, facing their fears during the grunge 90s reminds me of when I was growing up and learning who I was and what I wanted out of a relationship. I felt a special kinship to Janet Livermore, and looking back I think my dating life most resembles hers, how she fell for her guy friends and that scene of her hanging out with the phone by her side "in case he calls" was how I spent my dating days before finding my current boyfriend.
One of the most irritating characters by far is Debbie Hunt, a man-eaterish tv exec who decides to make a dating video using a service called "Expect the Best". She also is looking for Mr. Right all through the movie, and the scene where her videodate choice gets picked up by her roommate is priceless "$80 and I'll do the dishes all month" "Deal!"
In that vein, I found an actual video of dating clips from one of those services. It's kinda painful to watch now, but I guess I would have maybe dated the "early to rise" guy from the beginning of the video or "toxic waste guy" from near the end.
On a sidenote, it was only recently that I realized that the guy who plays the mime in Singles is actually Eric Stoltz, one of my favorite heartthrobs from the John Hugues-era Some Kind of Wonderful.
EDIT: I found out via The NY Daily News that the Seattle complex where the Singles lived still stands:
"The “Singles” complex was an apartment complex located in Seattle’s Capitol Hill (19th st. and E. Thomas) and is still standing, with the same yellow paint, today."