"Find Love. Guaranteed." --Match.com tagline

I have a friend--let's call her "Ruby"--whose dating life has lately experienced a dry spell. Worse than a dry spell, actually--more like a dry spell interrupted by intermittent acid rain. Things reached a crisis late one night, and in a fit of defeated desperation, she got out her credit card and pressed the button that sent $39.99 to Match.com, securing her a one-month membership with the online dating service. She told me of her decision the next day, and began a month-long quest for love through online dating. Naturally, I was suspicious of the whole endeavor from the start, but at the time I could not adequately explain why Match.com seemed so sketchy.

"Their ads are lame," I told Ruby (some of whose experiences described here are actually those of other friends of mine; I was keen to protect her anonymity). "You're young and beautiful, and you live in a city! Why are you wasting your time on strangers?" But Ruby grew up in the Midwest and has never managed to shake the conviction that dogged work is correlated to success in all realms, and she was determined to apply herself strenuously to dating on Match.com.