I went on a dating memoir binge and found three pretty decent ones. (That is to say, most of this variety are bland). Here are some good prospects for Valentine's reads.
Straight Up and Dirty by Stephanie Klein
Klein married young and got divorced in her twenties. Her memoir explores her time with the "wasbund" and the dating she dove into a month after the divorce. She ultimately discovers (with a therapist's help) that she has much to learn about herself before she can truly be in a healthy relationship. It's a common tale told with a light-hearted and often funny voice.
I Don't Care About Your Band: What I Learned from Indie Rockers, Trust Funders, Pornographers, Faux Sensitive Hipsters, Felons, and Other Guys I've Dated by Julie Klausner
Klausner, a writer for VH1's Best Week Ever, is in her thirties and she's dated all kinds (as the sub-title suggests). She's not completely jaded, though, she declares at the beginning that she "love(s) men like it is my job.”
Dating Amy: 50 True Confessions of a Serial Dater by Amy DeZellar
Another thirty-something navigating the dating scene, an unemployed DeZellar moves to Seattle and begins a blog about all the dates she goes on throughout a year. She doesn't see 50 different men (some stick around for more than one date), but this one's a silly and quick read about just how easy it is to suffer a really, really bad date with what had been a promising prospect.