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

Why Not?

I’m pretty sure I haven’t told this story here.  If I have it was a while ago, and it’s totally relevant to my last couple of posts so I’m going to retell it.

I was young, in my early 20s.  And I’d gotten sick.  Really sick.  One of those bizarre, mysterious (non-contagious) illnesses that land you in the emergency room and then get you admitted to the hospital for several weeks.  That’s right, I said weeks.

Besides the fact that I felt like shit, I was getting more depressed with each passing day.  Sure, friends and family would come by to visit.  But I was trapped in the hospital.  Oh, and I was NPO which means I was being fed intravenously.  I wasn’t even allowed to drink water.

The only thing that kept me from losing it was that one of my doctors was totally hot.  HOT!  And not only that, but he would take a few minutes each day to come and hang out with me.   It felt like he was flirting with me, but I couldn’t tell.  For starters, I looked nasty.  I was only allowed to shower every few days and I was pretty weak.   He was this gorgeous, older (about 12 yrs older) doctor who could have any woman he wanted.  Eventually I chalked it up to him just taking pity on me.

Jump ahead a few weeks.  I got better and was released from the hospital (no, I’m not going to say what was wrong with me – too much detail).  A couple of weeks after my release I had to go back for a follow up appointment with the hot doctor.  I got all dressed up and made sure that I looked good.  I figured that if there was any chance he really was flirting with me, I wanted him to know I was interested.

He said I looked great, but that was all.  He didn’t ask me out, or even hint at it (what was I even thinking, that would have been totally inappropriate).  I left feeling let down, but I wasn’t ready to give up.  I went home and called information (Yeah, it was that long ago.  I didn’t even know how to use a computer back then.) and got his home phone number.  Luckily, he had an uncommon enough last name and I knew what neighborhood he lived in from one of our flirty chats.

And then I called him at home and asked him out.  Yes, it was insanely awkward.  I’d never done anything like that before.  I’d introduced myself to men at bars, but never actually asked someone out.  But here was this man who I liked, OK – who I had a huge crush on and who I thought might like me back.  I figured we’d never see each other again as doctor and patient and that if I didn’t do something we’d probably never see each other again period.  So I did something.

He said yes.  Not right away.  First he said that he didn’t think it would be appropriate.  I said I understood and was about to hang up (and then go eat a pint of ice cream) when he said, “but as long as no one finds out it’s fine”.  And so we went out.  Several times.  Over the course of a couple of months.  And it turns out that he was actually a total asshole.  Arrogant, selfish and mean.  But that’s not the point here.

Since then I’ve done some equally ballsy things.  Nothing quite as dramatic, perhaps.  It always comes down to the same thing, though.  Why not?  What have I got to lose?  What could I gain?

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6 to “Why Not?”


  1. Alicewillbe says:

    Great story. Sounds like you’re psyching yourself up to do something equally ballsy soon? Do tell. :-)

  2. Teifion says:

    Well that puts my slight illness of several weeks into perspective (on the upside I’ve lost what little gut I had!).

    It’s a great attitude to have and generally the one I have, however it’s not so applicable if you know the person. A friend of mine recently had a friend of theirs ask them out, the two broke up a few weeks later because it simply wasn’t working but it’s been a little awkward between them. In that instance there was something to lose.

    Of course, if you’re trying to pull somebody that you may never see again then yeah, you have nothing to lose but your pride and lets face it, that’s something we hate seeing too much of in other people so odds are we can shed some of our own.

    Good to see that even though it never really worked out but that it taught you such a valuable life lesson :)

  3. Simone Grant says:

    -Alicewillbe
    Thanks darling. I think I am psyching myself up for something big. Though I’m not sure what. Hmmmmm.
    -Teifion
    Yes, altogether different if it’s someone you know and have to see again. But still worth the chance, I think.

  4. Dont Be a Slut says:

    I so absolutely admire you. I do not, and never have had, the nerve to throw my cards out on the table like that. Way to go!

  5. Simone Grant says:

    -Dont Be a Slut
    I’ve never been particularly risk averse, in any area of my life. That has proven to be both a pro and a con. I’m not sure anyone should be admiring me for it :-)

  6. Veka says:

    Good for you! I know there’s so many women out there that don’t have the courage to do that type of thing.

    On a side note: And it turns out that he was actually a total asshole. Arrogant, selfish and mean. I think that’s how it is with every sexy single doctor. I dated one a few weeks ago, and he was the same way! He knew he was attractive and he acted it. Bzzz. Next!