Miss Margo’s Prime Directive in Dating: Don’t Bore Me (or Make Me Feel Like a Jar of Cookies)

     I decided that I was sick of being bored and sexually frustrated, so I finally got off my ass and scheduled a date for this evening.  It took about six seconds.  I did it via IM–the guy, Matt, has an iPad and a BlackBerry, so he is always online.  Fucking always.  


      This will be my seventh or eighth date with Matt (we chat via IM on occasion when the mood strikes me, but that doesn’t count) .  If I sleep have sex with him, it will be the third time.  At this time, I completely expect to get some action, but with Matt, you never know.  As you will see, Matt’s batting average is not very good with me.  He has a history of spectacularly blowing it and then being shelved for many months until he charms his way back in to my orbit or I forget about why exactly I chose to shelve him (or both). 


       I met Matt almost three years ago on the internet.  He took me out to lunch at a great spot in Midtown which is currently defunct.  I had lamb, he had the salmon.  He was charming, appreciative without being obsequious, and handsome–he looked like a cross between Keith Olbermann and Clark Kent.  Good looks in a man are not nearly as important to me as they are to some women, but still, it was nice to look at him.  Attended a prestigious private university, but I detected no school-snobbishness about him (NYC is full of Ivy-League pricks). And he had a great suit!   


      There is no reason why Matt should not have had casual dates with me on a semi-regular basis (or, as my good friend and former housemate used to say, “been put into rotation”), except for the fact that he has something wrong with his ‘filter,’ as it were.  For the life of me, I don’t understand it.  It really is the damnedest thing.  The guy is an extrovert.  He is very easy to talk to.  Charming, really.  The popular guy who never used his popularity to be a total asshole. He has plenty of brain cells to rub together, too.  And then he will blow it somehow, out of nowhere, for no discernible reason.


      Here, gentle reader, I’ll give you a taste of what I’m talking about: on our second date we were canoodling in the back of a dark, romantic bar.  This was back when I was still drinking, and we were both kinda toasted, but even still…


       Matt said, with all sincerity and enthusiasm: “You’re so beautiful in that dress!  You’ve got a great figure.  I’ve always liked small breasts!”     


      I mean, really.  And lest you go, “Miss Margo, you are being a heartless bitch, everyone puts their foot in their mouth sometimes!” let me assure you that 1) I agree with you and am generally patient, tolerant, and forgiving–more forgiving, perhaps, than he deserves–I am not a fucking NGO, after all, I’m not obligated to take everyone, and 2) the guy has done or said something like this on multiple occasions.  There’s no rhyme or reason to it; there’s no way to anticipate when he’s going to embarrass himself and ruin everything and not even understand how he’s done it.  One time he showed up drunk, just absolutely tanked, for example.  The first time we had sex, it was a lot of fun, and let me tell you, I went to bat for that man–pulled out the special effects, if you know what I mean.  I like sex and I’m good at it. (FYI: Sexually, Matt is a normal regular dude with predictable desires.  Which is fine.  So that is what we are talking about here)  Every other dude in the Tri-State area would think, “Wow, I have something good here, let me do what I can to secure access to it in the future.”  Matt has certainly tried to secure access–if he hadn’t spent 467,900 man hours of productivity perusing me relentlessly from the moment of initial contact, we wouldn’t be in touch today.  And he apologized for showing up drunk the last time he came to my apartment.  But the fact is, he still showed up drunk.


       The requirements I have for men whom I pick to date for recreation are minimal; the rules are simple and straightforward.  I don’t play games with this.  The Prime Directive is: Don’t Bore Me. I have complete faith in your ability to do this; if I didn’t think that you could manage it, I wouldn’t fucking be here in the first place.  It is true that I no longer think that I am capable of being seduced, but I still expect you to TRY.  Like many teachers, I give extra points for effort.   So show up on time, wearing something nice.  Entertain me with conversation for a few hours.  I know that you can do it, otherwise we wouldn’t be here.  And what’s more, I’ll help you, because I like you, and I’m interested in you, and when I feel like it, I am a fascinating and witty conversationalist.  After all of that, I will let you into my apartment.  Be considerate of my needs in the sack (again, I’ll help you–sexually, I’m like the Social Security program, in that I pretty much run myself with Prussian efficiency…and oh my God, did I really just write that?), mind your sexual manners (any complaints about condoms and you will be banished forever–a resigned sigh is acceptable and understandable, however), don’t automatically presume that you’re spending the night.  If you give me fun and satisfy me, you will probably have the opportunity to do it again in the future.  It’s just that simple.  It really is.  


So for tonight: WILL MATT BE GOOD COMPANY FOR FOUR HOURS AND NOT MAKE ME FEEL LIKE I WAS A JAR OF COOKIES AND HE WAS FIVE YEARS OLD?  


Update tomorrow!


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