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

Learning New Tricks

I have a tomorrow night with a guy I first “met’ months ago (pre Mr. Potential).  We met online, exchanged a few emails and then spoke on the phone.  I liked him well enough – he seemed smart, funny and enthusiastic about his life and work although he was a teensy bit of a name dropper (really guys, I don’t care who you know or who you’re related to).  Anyway, we made tentative plans but then something came up (I can’t remember the details) and he had a business-related trip the next week.  I never heard from him again and I wrote him off as one of those guys who was just in it for the quick lay, figuring he’d already moved on to someone who hadn’t heard his shtick.

And then I got an email from him last week.  Not just an email.  Two messages via the online personals site (), a regular email and a phone call.  All within an hour of each other.  He was suddenly very anxious to reconnect with me.

I didn’t answer the phone when it rang because I didn’t recognize the number.  But after some thought I decided to reply to the emails.  And after a couple of quick emails he called again and we spoke briefly and now we have very definite plans for tomorrow night.

And so.  I find this kind of bizarre.  To be honest, I’m going against my instincts here.   My instincts tell me that if this guy was interested in me, I would have heard back from him a long time ago.   And that not hearing from him until last week is a big . Honestly, my gut was telling me to not even reply to the emails.

But I’m trying to rethink some of my old assumptions.  Learn better ways of reacting to guys.  Be less suspicious.  Be more open.  And I figured it wouldn’t kill me to give him a shot and find out why he disappeared and then reappeared.  I’m hoping he’s been in a relationship this whole time.  Then all I need to worry about is not being his rebound girl.


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13 to “Learning New Tricks”


  1. starangel82 says:

    I’m proud of you for trying to rethink your old assumptions. It’s very big and brave of you. I do hope this guy turns out to be a good date or at least you get an answer as to the disappearance then sudden reappearance. Good luck dear!

  2. Anonymous says:

    Instead of worrying about your gut and your instinct, why don’t you just *ask* him for crying out loud?

    All this uncertainty bouncing around in your head? He has no idea about this. And so now you’re going on a date with him with your guard up, on the hunt for red flags, and he has no clue what kinds of tests you might lay out there for him.

    Here’s the flip side. I exchanged emails with a girl and we went on a couple of dates. They went well, but recently she has not been responsive. But if I ask her what’s up, I’m in danger of Not Knowing What She Wants Without Asking (which you listed a while back as one of the top five things women want).

  3. Cute~Ella says:

    Rethinking old assumptions is one thing and is an awesome idea…BUT if your gut is genuinely saying NO then you should probably listen. I don’t know about yours, but mine is never wrong.

  4. Singlegal says:

    Sounds to me like he was dating someone else and it didn’t work out. I think it’s probably a *good* thing, if he was choosing not to juggle. Of course, he could have been extradited on jaywalking charges and “unavailable” until trial … but try not to thing about that :-)

  5. SerialSinner says:

    I think the sudden big anxiety for meeting you is strange (2 messages, email and call in 1 hour?). It might be worth giving him the benefit of the doubt, but I’d be looking out for potential big personality issues…

  6. Simone Grant says:

    -starangel82
    Well, I don’t know about big or brave but I figure the way I’ve been doing things for all these years hasn’t worked out all that well so I might as well try the opposite.
    -Anonymous
    I will ask him, on our date. I’d rather be looking him in the eye when I ask and he answers. Truth is, I don’t think phone or email are much good for questions like that. In response to your situation, I think you’re misinterpreting what I meant. In fact, I’m sure of it. If a woman has stopped responding to your communications and wish to continue seeing her, then you have every right to ask what’s up. You shouldn’t be expected to read her mind. I was referring to the ability to be able to make plans. I cannot stand (nor can many women)a man who leave everything up to the woman, “what do you want to do, where do you want to go”.
    -Cute~Ella
    Truth is, my gut’s wrong all the time. Sucks.
    -Singlegal
    True, he could have been in a foreign jail this whole time. Hmm.
    -SerialSinner
    Yeah, I think it’s a bit odd. But I’m trying to be open minded here.

  7. Alicewillbe says:

    I dunno. Am I missing something? Exactly what did this guy do wrong? Ask to take you out on a date when he actually feels ready rather than when he didn’t?

  8. Veka says:

    I know people who have been guilty of this. When “talking” to someone that they could have potentially dated, and then ended up meeting someone else, they stopped all communication with the first person, in pursuit of something with the second person. When things with the second person don’t work out, they try to see if there’s still any chance with the first person. Not saying this is the case here (and certainly not trying to be the bearer of bad news), but that’s what came to mind as soon as I read this post. At least he made concrete plans! Good luck and have fun on your date!

  9. Jennifer-from-NY says:

    Wow people got really heated. I just read this as a few thoughts pre-date. I think you’re doing the right thing: both to ask what happened and be a bit wary, and to go out with him. And I agree with Veka that that could be the case, but if so why is that a bad thing? He could have been interested in someone else without being a bad guy or disliking Simone.
    I wish yall luck!

  10. Momma Sunshine says:

    I dunno. I’m a firm believer in not making assumptions…there could be any number of reasons why you haven’t heard from this guy. Sure, it’s possible that he’s a dick, but there could be lots of other explanations, too. It’s probably a little unfair to judge this dude based on the gross errors of all the other males on the planet… heh.

  11. alfabeta says:

    Everyone deserves a second chance. Go for it!

  12. Simone Grant says:

    -Alicewillbe
    I don’t think he did anything “wrong”. But we were supposed to go out about 6 or 7 (8?) months ago and then he disappeared without explanation. And now he’s back and superanxious to go out. Not wrong. But honestly, it sets off my red flags.
    -Veka
    That happens all the time. Though I think the mature way to handle it is to send an email saying, I’m met someone else but it was nice meeting you. I just got one of those emails today and if that guy emails me in a year and says, it didn’t work out, and I’m single then I’ll date him in a second. No weird feelings.
    -Jennifer-from-NY
    These are just some thoughts pre date. I don’t think anyone’s getting heated?? The date is tonight so we’ll see.
    -Momma Sunshine
    I’m trying to get to that place. It’s hard. I want to judge each guy on his own behavior and not the behavior of the ones before him. But it can be so hard.
    -alfabeta
    EVERYONE???? Oh, allright.

  13. piter says:

    Just want to thank you for very informative post, regards Ed