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.