This happened four years ago (at the time I was 27). I was in grad school, finishing my thesis film and going through a kinda-sorta slutty phase. I lived in Chicago with two roommates. I strongly felt--fuck that, straight up knew--that my thesis was superior to the work of all my colleagues. This made me supremely arrogant and in some ways insufferable, but the upside was I oozed self-confidence. And I was enough of a workaholic that I needed a pretty high volume of sex just to make me unwind and gratify me. So from the fall through March I'd had my fair share of conquests; mainly one night stands, usually coupled with plenty of alcohol. You could say that, ultimately, I was just lonely and troubled.
In April I began seeing a woman I met on OkCupid named Lauren. She was African American, about two years younger than me, wore her hair in a bob, nerdy-cute in her glasses. She had recently moved to the city and worked a well-paid job as a sales associate at a bra retailer. I swear I am not making that last detail up. We talked on the phone first--she was apparently looking for boyfriend material--then met for lunch that weekend. She texted me a picture of herself to show me what she looked like. Simply from sending me that picture I got the sense that she was the type who would sleep with someone on the first date. Which made me glad, especially considering I carried a condom in my wallet.
She was a little late to lunch and apologetic about it. We somehow didnt have much to talk about on that first date but still hit it off. She wore a cutoff blouse and had thick arms. She suggested we go back to her place and hang out and I pretended to be a little taken aback and hesitant. She apologized again and said she understood why that sounded wrong. So I told her it was okay and said sure, we can hang out for a little while.