Dateline: "I'm out at 2 a.m. on a work night with a guy whose last name I couldn't tell you, who pays for everything with huge wads of cash...."

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Female, 26, PR coordinator
with
Male, 33, professional athlete

7:05 p.m. - "Hey grgeous, I was thnking abt u all wkend. What r u up to 2nite?" It's the professional athlete I went out with last week. He's following up on our "plans" to hang out tonight. I wonder what kind of phone he has, and get the feeling he works harder at coming up with these abbreviations than if he just wrote out the actual words.

7:15 - This sounds super-shady, but if I've learned anything in the past year it's that professional athletes love to picture-text.

7:20 - He says we can meet around 11, and he'll pick me up at my apartment. He has clearly never worked a regular job. I agree anyway; random plans at odd hours make my routine more interesting.

11:10 - He texts me when he's outside my building, and I come downstairs. He's sitting in his black SUV (with tinted windows!) waiting for me. A few of my neighbors are around, and I hope they notice me step into his car. I feel like hanging out with a football player on a Wednesday night gives me an awesome new dimension.

11:35 - He takes me to a jazz club in the West Village, parking the car on a side street. A couple walking past sees us and does a double-, then a triple-take. I can't tell yet if the attention is positive or negative, but he won't have any of it.

11:40 - "What you looking at?" he shouts. I'm about to suggest he keep his voice down, that we might get into something. But then I remember who I'm with: a 6'5", 300-something-pound, football player who, honestly, I'm a little afraid of. The couple actually scurries away.

11:45 - We walk into the jazz club, and he starts to order us cocktails at the bar. Before he can finish, he gets interrupted as two men greet him and ask to shake his hand. He's polite but looks distant and mildly disinterested. He turns away, puts his arm around me and asks what I would like to drink. "Do you know them?" I ask. He shakes his head no.

11:47 - We sit down at a table and listen to the music. We don't talk much, but we're both ok just sitting and people watching.

1:05 a.m. - We finish a second round of cocktails then head to a different place.

1:25 - We are standing at the new bar, and a man who is down on his luck and clearly very drunk — to him, we resemble an actual couple — starts talking to us and asking for relationship advice.

1:42 - He tells us of an ex-girlfriend he's trying to win back, but she's stopped responding to his texts.

1:47 - I haven't been in a real relationship in over three years, I'm out at 2 a.m. on a work night with a guy whose last name I couldn't tell you with complete certainty, and who pays for everything with huge wads of cash. The room is spinning a little. I'm in no way qualified to give relationship advice.

1:49 - My date tries to comfort him by telling a story about how he almost got shot in Virginia Beach when he was caught in bed with a military guy's wife. His story seems to work, and the man forgets about his troubles, at least for the moment.

1:58 - My date finishes his drink and notes that there is a massage place across the street.

2:09 - We head over to get back massages. I negotiate him down from a ninety-minute session to a thirty-minute one. I need to make sure I get a good night's sleep for work tomorrow. Er, today.

2:23 - The massage is great but my mind wanders. I think about how my parents probably would never guess 90% of the things I do.

2:45 - We head back into his car. He wants to make one last stop at a club downtown.

3:01 - We pass by W.i.P., and there is a huge crowd of people outside. Apparently Drake and Meek Mill are there. He stops his car in front, and tells me I can wait inside if I want while he checks it out.

3:02 - I watch as he says hello to a bouncer, who lets him in immediately.

3:04 - He comes back out and in to the car. "It's messy in there," he says. "It's like a riot or something might happen. We can go in if you want though, it's your call."

3:06 - We decide not to go, and instead make a pit stop at a local bar on the way back uptown. It is a sad crowd at 3 a.m. on a Wednesday night. We leave almost immediately.

3:15 - We go back to my apartment, and (in his words) "chill just the two of us" for a little while. He leaves around four.

7:00 - As I wake up and get ready for work, I see I missed a text from him while I was sleeping. "It's a gd thing we left wip. Some1 frm Drake's crew strted a fght & threw a bttle that injred Chris Brown & othrs." I consider making some drastic changes in my life.

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