Am I Jaded, Cautiously Experienced, or a Perpetual Bachelorette?

26 Feb

Since many have been asking for an update, I figured now was a great time. I’m slightly hungover, extremely tired, and in need of a small break.

Date went well – we met up for a drinks that, I think, he and I both thought would only last a couple of hours (tops.) He even admitted he thought of bailing on it earlier in the day (what nerve! HARUMPH!)  Anyway, what we thought was only going to be  a one or two hour date turned into a five hour one.  Great conversation, learned a lot about each other (I’m debating whether too much on a first date), and we even set a second date for tomorrow night (YAY!) And yes, we may have even smooched a little.

But every time I date someone new, I have to question – am I jaded or cautiously experienced?  I’m going to take a line from Sex and the City: I’ve been dating since I was fifteen! I’m exhausted! Where is he?

I have a lot of experience going on first dates and I’ve realized I look more at the bad than the good in people.  Maybe it’s because I’ve been hurt deeply by a couple of men in the past or maybe it’s because I’ve been on SO MANY DATES over the years, but I seem to pick at a guy (in the privacy of my own home ) than actually looking forward to spending time with him. Weird and wrong, I know. Trust me, I know.  I’m trying to change. It’s hard.

BSF and I were having a similar conversation on this topic – stay tuned for her musings later on. And as she is an Optimistic Ollie, she already “yelled” at me over IM when I said “maybe I’m always going to pick at a guy and I’m just meant to be single for the rest of my life.”

Another thing that I think about is – how will my friends and more importantly THEIR husbands take to this new beau?  Trust me, I had a conversation with EatDrinkBreatheSweat earlier and said I’m really concerned how her hubs and how Life by the Day‘s hubs think about the next guy I bring over.  Why? B/c I’m nervous they’ll see bad things I’ve missed.  Which I think is so sweet, because they only want the best for me and I know they’ll tell me the truth.

These are some of the reasons why I think I should be a perpetual bachelorette. I worry about any flaws this dude will have, how I will handle it, and plus, I don’t like anyone messing with my routine.  Is that wrong?  Don’t answer that – I know it is.

Just give me advice on how to change this mentality of mine…


4 Responses to “Am I Jaded, Cautiously Experienced, or a Perpetual Bachelorette?”

  1. jolene1079 February 26, 2010 at 2:42 pm #

    Thanks for the shout-out friend! 😉 And I don’t think there is anything wrong with your cautiously experienced self – just take it day by day, the “we’ll see” approach I love so much. We’re in this together, right?? And I totally know what you mean with the whole intro-ing a new guy to friends and family. I haven’t ever gotten that far with anyone I’ve dated yet and no matter what, it’s going to be way more stressful than it should haha! XOXO!

  2. Dee February 26, 2010 at 4:24 pm #

    when you meet the right guy you’ll like his “flaws” and all! I’m so happy it went well!!! I knew you would make out with him! ha.

  3. jsutera654 March 1, 2010 at 6:28 pm #

    I agree, nothing wrong with being cautious, going in eyes wide-open. You’ve been burned before, you are trying to prevent that from happening again. But on the other hand, you should also trust your gut. I know it’s hard to do when you’re fearing the worst, but it’s the only way to truly BE in the moment with a new guy. And trust me, Scott (aka “your boyfriend”) only looks out for ya, he just wants the best for you cuz he loves you 😉


  1. Dating is Easy, Relationships Take Effort « This is Why I Date - March 10, 2010

    […] I can date half the men in Boston – hell, I feel that I have, but actually moving that from dating to a real relationship where you have to care about another person and take their feelings into consideration, is the tough part.  Hence, why I have to pose the question AGAIN of whether I am jaded or cautiously experienced. […]

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