The Dating Dilemma – An Anatomy of My Love Life

I’ve always considered myself a pretty good date.

A charming and witty conversationalist, respectful, flirty at the right moments, very good at avoiding staring at your boobs and seemingly the best good luck charm a gal could ask for.

Remember that movie Good Luck Chuck? Well, it’s quite possible that is based on me.

There are two kinds of girls I date.

The first kind is the girl who has such a good time with me, that a week or two later I find out they are actually back with their ex, or with the new love of their live. This, of course, would explain why they never replied to my text messages or emails the day after we went out. If I had a dime for every time this happened I could quite possibly have enough cash to buy an illegal green card.

I’ve done the dinner and/or movie thing with a fair number of girls over the years, and in fact a lot of you are probably reading this right now (especially if you found your way here via my Facebook profile) and remember that time you and I went out. We had a pretty darn good time, and of course when I tried to request a follow up “meeting” there was always something going on and before long you were in another relationship and didn’t wanna ruin our friendship. This of course made our friendship tense for a while, until you broke up with whoever you with, then we spoke again, until you met the next in a long line of “loves of your life”.

More often than not I’ve been told I’m too intense. Amazing considering I never once made a move, or offered you a ring on our first and only date. Hey, I can take a hint, I’m a pretty smart guy, but I just wish people would stop making lousy excuses like that.

Heck I can’t even bring a girl back to my place for dinner or “dancing” (My mom wouldn’t wanna miss her crime stories.)

The second kind of girl I date is the kind of girl who doesn’t know she’s on a date with me.

These are the weirdest most awkward evenings. To my own downfall, I have always been better friends with girls than guys, and therefore get shoved into the friend’s zone by default and spend the next few months (or years, depending on the size of my obsession).

Whilst I have “hung out” with a lot of the female friends, there is nothing worse than asking a girl out only to find out she thinks its as friends…and you have to play along with the ruse the entire evening. It’s heartbreaking! Let me tell you. The minute she starts asking for advice on the guy she fancies…everything turns to slow motion, and it becomes the longest night of your life.

I haven’t been on anything close to a date for a few years now, and if I have, I’d love for the person to let me know it was an actual date, because I think at this stage of my life I can’t even tell the difference anymore.

Anyways. Let’s fast forward to the here and now.

Yes. I am currently interested in someone (and yes that could mean plural). I’ll talk about one as I know she in all likelihood doesn’t read my blog so I can get away with being completely honest and not making a fool of myself.

I’ve asked her out to movies this week…tomorrow night in fact. She said yes almost instantly, which is a rare enough for me to just die happy now, but of course, she probably sees it as friends.

Is she single? Yes, I as far as I know. Is she interested in someone else? Probably. They always are right? Does she know how I feel about her? I haven’t the foggiest. I like her, I like her a lot actually…she checks all the boxes I am looking for in a girl, and more importantly she fits perfectly into the bigger picture of my life. I’ve known her for years now, and we are only just rediscovering our friendship. I fear that’s all it would be though.
I’ve made the mistake too many times in the past of revealing my feelings to someone, so I won’t be doing that anytime soon…unless she happens across this blog in the next 24 hours, in which case movies tomorrow night is clearly off.

Right now I’d rather risk her never knowing just to spend time with her, than to tell her I’m interested in anything more and scaring her away for a number of years.

So that’s my dilemma. I consider her my date for tomorrow. I consider her my date for a wedding she’s agreed to go to with me, and I consider her my date for New York City.

But I guess to her…I’m just this awesome friend she knows.

Are there any clues so that I know she feels like she’s on a date too? I mean other than if I’m making her breakfast in the morning…and we’re having waffles!


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4 Responses to “The Dating Dilemma – An Anatomy of My Love Life”

  1. Former Date Says:

    Here’s what I think:

    Stop playing it safe, hoping that if she doesn’t have feelings for you now that she may come around later, that maybe she’ll change her mind once she’s over her ex/less busy at work/in a place for another relationship/…

    You’re a catch NOW. And I could be wrong, but you’ve got just about as much female friends as you can handle…. you’re not looking for another, especially from her.

    So walk in there, be your funny, chivalrous (and how!) self without giving her the keys to your heart and leave early. Let her work for it a bit…

    If she cant see that you’re her man… her loss, cos you’re sexy dammit… and you know exactly how to treat a woman.


    • The Burg Says:

      Leave early …like before the movie ends? That’s um…yeah.

      Thanks overall though “former date”
      Wonder which category u fall into…

  2. patissonne Says:

    This is such a sweet post!! The line between friendship and a love story is a fine dangerous line to tread, to cross… I hope all works well for you, wish you all the best of luck for the date, and please keep posted about how it went 🙂

  3. mariahilldublin Says:

    As a girl who has more guy friends than girl friends – I understand the problem. Best of Luck.

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