the week of ROG, AKA the weirdest 2 dates of my life

Dear Prep,

So many apologies for the delay in response. I would send you 394739279 dates if I could as an apology, but it sounds like you've been doing quite well for yourself and thus I will let you continue living your life of dating leisure.

First things first, I would like to address your comment that "a woman is, on average, less of an idiot than a man" from your previous post. I am very pro-women's-rights, but I literally read this and LAUGHED. This is interesting to me for a few reasons. 1) I just spent the day talking to smart women who ruminate about the stupid things that males do and overanalyze why this occurs, 2) most of my male friends are not idiots as far as I can tell, and 3) a lot of women want to find boyfriends and if boys are so dumb, then doesn't that make women dumb if they want to get together with someone dumb? (A little circular, but hopefully you'll catch my drift.) It really has become disturbing to me how much women analyze what men do. Seriously, if he likes you, he'll probably call you, so why do you need to know why/why not?

I'll get to my dates this week and will then address yours (three?!!!! bow chica wow wow). I ended up being a little monogamous (don't hate the player, hate the game) and went out with the same guy twice in a row. Which guy was this? Why, Really Old Guy who bought me drinks last weekend. ROG texted me and wanted me to meet him, but I had two birthday parties to attend and no time to spare. You know, a girl's got to keep her social life. Anyway, around 1AM I decided that my social life was sleepy, so my friend and I left the bar and went home. ROG continued texting until about, oh, 3:30AM and I coyly said that I couldn't meet him because I was still at my friend's party. I mean come on, a priss doesn't "come dance with me at the W" with some shady guy at wee hours of the morning. It just doesn't work like that. Regardless, his texts were pretty endearing.

The next day I figured, hey, what the heck? I've never been out with a ROG and I want to do that. Life's for living on the edge! I sent ROG a text about his night before and lo and behold, he invites me to a jazz show that night. Sweet! I agree to go and end up getting there on time (for shame) and have to wait 15 minutes before he and his entourage arrive. His entourage includes a woman, clearly older than me and closer to his own age, who gives me a little bit of a look of disgust as we are introduced. ROG simply tells me the name of each person in his party without any qualifiers such as, "this is my friend so and so, this is my sister, this is my brother's girlfriend", so I have no earthly idea who this woman is. We sit at the table and my back is inevitably turned to ROG and this chick because of where ROG places my chair, so I'm forced to watch the jazz while ROG and Chick whisper behind me. This obviously pisses me off (I'm the priss and don't deserve to be treated like this.

I can only make one conclusion - I must be on the tv show The Bachelor! I can't believe that ROG has done this to me; why would he invite me to something where he's clearly invited another woman? I begin to get fumingly mad and decide that I might just leave since it's so awkward and weird and uncomfortable. Two seconds later I figure, F this! I like jazz! I'm going to watch it and enjoy it! I am a strong woman and I can handle this situation! This gives me renewed vigor just in time to see Bachelorette pay for her drink and ticket and leave, so I am elated and rush to the bathroom so that I can return to the table and swipe her now emptied seat. It was a clutch move. I start asking ROG generic questions, then eventually get to the questions of who everyone at the table is (ie, who the hell was that Bachelorette and what the hell is going on here), and he explains each person's status and says that the Bachelorette is his brother's friend from high school or cousin or something like that and says, "so do you see where you fit in now?[smiling]" I frankly didn't know if I did, so I just said, "Well... I guess..." and sipped on my drink while enjoying the music, which was nice.

So, the jazz ends and ROG and his friends are talking about the business they're in, which is really enrapturing if you're a female because it caters to females and involves shiny things. And I have a strong penchant for shiny things, as we know. Then the bill comes and ROG whips out a hundy and pays (I guess there were tickets since we each only had one drink?) and asks if I want to get drinks. I figure, suuure, why not? We went to grab drinks around my house, which was the other side of town, and it ended up being fairly fun although still somewhat awkward due to the weird start. He walks me home and says, "oh, what day is this... oh, what are you doing tomorrow?" to which I respond that it's a Monday and I typically don't make plans on Mondays. So he asks me out again for the next day for dinner! The balls! And of course I had to say yes based on the plotline thus far.

The next day he's texting me from lunchtime until about 5 and we decide that he'll choose where we go for dinner around 8. I get a text at 7:40 that says, "know a good place in midtown?" No! I don't know a good place in midtown, especially 20 minutes before we were supposed to meet when I probably needed to leave at this time! I text him that I just got home from work (true minus 20 min) and that I don't know a place in midtown and wait for him to respond with a destination, and he doesn't respond again until 8PM at which point he says, "I'll come to your area in about 10 minutes". Umm, what!? You want to not follow through AND tell me ten minutes ahead of time? I'm not going to sit around waiting to eat dinner with some dude who was late the day before and had some sketchy entourage with him! No way! I'm standing up for women everywhere by showing this guy that this is NOT acceptable/nice/thoughtful behavior! So, I promptly text him that I'm making other plans and need more than ten mins' notice. He texts that I can have 20 or 30 and then calls and asks if I still want to go. I tell him that it's not about the time, it's about the consideration, and that I thought that he would be nice enough to tell me where to be and when (as we discussed) more than ten minutes in advance without a plan of where he actually wanted to eat. He persuades me to come eat (asking people on the street, telling me we'll have fun, etc. etc.) and I really have no plans at this point anyway, so I decide to go because it will be interesting. We agree to meet in 30 min, so I finish getting ready and then sit around in my apartment for 20 minutes, just because I'm pissed off and I can. I don't take crap from guys, even if they're old and rich. They should know how to treat people nicely.

The strange part is, when I arrived, ROG apologized and the date ended up actually being really fun and lacked the extreme awkwardness of the previous night. We talked and talked and ate dinner and went for drinks and I ended up getting home at 1AM after discussing whether he usually dates young women, that he had meetings at Cartier that day, etc. etc. He walked me home and asked if I was coming to XX (the city where he lives) to which I said no, and then if I would go to Vegas, to which I said sure. We'll see if anything transpires, but who invites someone they've known for a weekend to Vegas? Who?!

It was interesting to say the least. Will respond to your dates soon, but am very impressed with your work thus far - ballin' and shot callin'.