Real stories about dating and relationships in New York City. Truth is more interesting than fiction.

Dumb and Dumber

Fact: I like men.

Fact: I don’t have as much patience for dating as I used to. Maybe that’s a good thing. Or a bad thing. Whichever.

So as I mentioned, I spent some time this weekend hanging with a girlfriend comparing our Friday night dating disasters. My story was short. Short, silly and pathetic.

I was supposed to have a date. But I’d had emergency dental work a couple of days before. And so I texted the guy (someone I’ve been out with before, but not  a boyfriend or even a contender at this point). And I told him that I was feeling lousy and I’d love to reschedule. And I’d make it up to him. Tooth pain is not good for my mood.

He was cool about it, which earned him future points. And I was feeling good about him. Skip ahead a few hours and I’m lying in bed with an ice pack on my mouth watching something stupid on hulu. I get a from him, asking me to send a sexy pic.


Here’s how I feel  about the text me the sexy pic nonsense. If we’re seeing each other regularly and you’ve spent the night in my bed more than 3 times then OK, you can send me a text like that. Playfully. Knowing full well I might tell you to fuck off. Note: Dude has never spent the night in my bed.

Otherwise, you’ve gotta be fuckin kidding me.

I realize that I’m probably out of step with pop culture here. THIS seems to be what people do. But NOT ME. Ever. Never.

Anyway. I did not respond. And a couple of days later, I checked my outrage/shock/repulsion with a couple of friends. Each of whom told me I was OK to be creeped out.

I got another text from the guy a couple of days ago. I still haven’t replied. I, quite frankly, have no idea what to say. Sorry, dude, you’ve creeped me out.  Is what I’m thinking.

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13 to “Dumb and Dumber”

  1. That is weird. Context is everything.
    The Naked Redhead recently posted..How I Manage My Online PresenceMy Profile

  2. Dennis Hong says:

    Text him a sexy pic of your middle finger.

  3. Mel says:

    First off: EW.

    Second off: you should MOST DEFINITELY tell him that he creeped you out.

    This, guys, is unacceptable dating behavior!

    (but I must admit that I like Dennis’ suggestion of the middle-finger pic — passive aggressive, but totally awesome).
    Mel recently posted..{pursuit of Pittsburgh} The ToonSeum (and a giveaway!)My Profile

  4. Anon says:

    Am I the only one who thinks this is sorta cute?

    • Simone Grant says:

      I’m sure you’re not the only one. But this isn’t really a majority rules kind of thing. It only really matters how I feel. And I’m creeped out.

  5. D says:

    Hm. I can see why you might be a little creeped out, but your three-times rule is arbitrary. I’ve sexted plenty of women with whom I’ve only fooled around once or twice. In a couple cases we hadn’t even gotten busy once. In all cases it was well received.

    Now that I think about it, one woman sent me sexy pics on my request before we even met IRL. No, she was not insecure or emotionally damaged. Just playful. We hooked up a couple times, but she lives too far away for an (exclusive) relationship. She’s moved on to a very happy relationship with another guy, and we’re still friends.

    Yeah, while it ultimately only matters how you feel, that does not ipso facto mean he’s dumb.

    • Simone Grant says:

      My 3 times rules is entirely arbitrary and not entirely serious. It’s really just shorthard for = someone I feel very comfortable with. One of the best things about human beings, how completely different we all are. So not one size fits all. The women YOU date are comfortable with sexting. The guys I date need to figure out pretty quickly that I’m not. Or they won’t be dating me for long. This is someone who’s met me many times, and I thought had a pretty good sense of my personality. Yet totally misread me/the situation. I get to call that dumb.

      • D says:

        How do they “figure it out?” Do they know about your blog? Do you tell them you don’t like sexting?

        Starting a naughty conversation requires taking a risk. For a long time I was too much of a nice guy. Over the last couple years I’ve started amping up the bad boy side of me and I’ve found I attract more women. Not all of them, of course (I’m sure some would call me dumb too), but taking more risks has meant more payoffs in terms of relationships.

  6. DG says:

    A guy recently sent me the same text, and I sent him a pic of me sticking my tongue out in a decidedly un-sexy way.