Is This My Craziest First Date Yet?

Screen Shot 2013-09-18 at 2.16.18 PMHave you ever wanted to go visit a new city in a state you’ve never been to?  Have you ever agreed to go to that city on a first date with a guy you’ve never met?  Well, now I can say I have.  I’ve agreed to be flown to a new city that I’ve always wanted to visit, for a weekend with a guy I’ve never met.  Crazy?  I don’t think so.  He’s my close friend’s cousin, and I’ve heard about him since I was a kid.  She always looked up to him.

He got in touch with me for the first time on July 29th.  At the time he didn’t realize I was in Florida (he’s in NY) but that didn’t deter him.  Since then we’ve been talking and texting everyday.  It almost feels like we’re in a relationship already.  So much so, that I felt a little guilty going out with George, but my other friend talked reason into me… “You haven’t even met the other guy yet, just go out with George!”

I did, as you all know from my last two entries.

I’m really excited about my weekend getaway though!  He’s made all the arrangements, all the plans… which leads me to my Tweetable:

“Sometimes you just gotta fly by the seat of your pants” @50FirstDatesG

… and a seat on Southwest airlines 🙂

What I especially like, is that I’ve already fallen for his personality through talking to him, and though I have an idea what he looks like (he always sends pictures of himself from far away with sunglasses and hats), it really doesn’t matter because I’m already “in like” with him.  I know, I know… don’t set my expectations too high, but I can’t help it.  He doesn’t play games, he says what he’s thinking and he’s extremely thoughtful.  All qualities I look for.  So as long as he doesn’t call me a C-word or punch me in the face, the odds are stacked in his favor.

I leave Friday and get back Sunday.  My mom wants to know if he got us separate hotel rooms… I don’t know… flyin’ by the seat of my pants.

Next time you hear from me, you’ll know how it went.  Will Date #12 be it?  Will George call even though I didn’t sell him my leased car?  Will I really have to go on 50 of these things? These questions and more answered.. as my world turns.

What’s the craziest thing you ever agreed to on a date?

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13 Responses to Is This My Craziest First Date Yet?

  1. Sue Painter says:

    I’m not telling what the craziest thing is I ever agreed to do on a date, LOL. But yours sounds fascinating and I can’t wait for the FULL report!

  2. Jessica I can’t believe you are doing this! Yikes. I would be terrified but I guess you’re braver than I am. I would love to hear a man’s perspective on this first “date.” Good luck!

  3. On the edge of my seat!! Fun to think back and review my dating history. I’ve been single most of my life; so, I have been on a LOT of fun dates. 🙂 Nothing particularly “crazy” stands out, but I do remember a date in Italy that started in one town for a drink, moved to a mountain town for the specialty of the house to eat for dinner, another town (about an hour away) for dessert, and then to the beach for some dancing. As we were driving back home, the sun was rising. I just LOVED the way Italian men wanted to show-off their fabulous country and its offerings! 🙂 Thanks for triggering those memories!



    Katherine C. H. E.
    Author, Be True Rich

  4. The Geek says:

    Very cool

    I don’t think it’s totally crazy. You seem to trust him, and it’s not like he’s a total stranger.

    The craziest thing, which is not so crazy, I did on a first date I guess was drive 4+ hours with a woman I never met to go to an Air Show. (we did talk on the phone, and I had agreed to it). After 3 dates, I started to figure out I was her taxi service. LOL. I’m slow.

    The second craziest thing: I was dressed as a Viking that couldn’t swim at a Halloween party (the theme was “Under the sea”), and had an auburn colored wig on that matched my mustache. I had seaweed hanging on me and gave out little plastic crabs to all the ladies. People that didn’t know me were impressed by the wig’s split ends (result of the metal chain mail) and the color matching, and thought it was real. Then I met this woman … guess that was our first date. She asked what I did for a living. I told her I was a Captain the Marine Corps (I was). I had to take OFF the wig to prove I had a buzz cut. She was quite disappointed it wasn’t real hair.

    I ended up marrying her. Ironically about 4 years later when I got out of the Military I asked if I should grow my hair, and she didn’t seem to care or be interested either way. Then again, she’s now an Ex, so that settles that.

    == The Geek ==

  5. Heidi Alexandra says:

    OMG I need to know how it goes what is it – Sunday over there in the USA – the suspense is killing me. Don’t make us wait a whole week!

  6. Mitch Tublin says:

    Wow! This may be the best story yet!

    We left a party at a house by the beach. It seemed going to a party
    would be a good way to date early on in our relationship. The crazy
    thing we did? Went skinny dipping in the ocean.

  7. Mira Dessy says:

    Can’t wait to hear what you thought of your trip and your date

  8. This is so exciting! You just left us with a cliff-hanger. Can’t wait to hear how it went! 🙂

  9. What fun! he sounds quite the catch and I hope it’s a fun and romantic trip! and he is as nice in real life as he is texting 🙂

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