Tour Guide

My next official date with Dimples is this Friday. Somehow I came up with the brilliant idea that we should go stand-up paddle-boarding. I’m sure its going to be a hot mess.

BUT last Friday night I was out near where he works and sent him a text. It was the next day that I found out he had been working, and he responds “why didn’t you come see me? It would have been nice to see a friendly face.” Uh. What!? I didn’t know he was working and I’m not an actual stalker in real life. But I assumed he was flirting. I let him know that I would be out again in the flats with my friend, and jokingly asked if he wanted to play tour guide. I was surprised he agreed. Why does it always surprise me that he wants to hang out with me?!

My friend and I are finishing dinner when he texts me that he is off work. He says he is bringing a friend. Uh ok. That’s cool. This is the first friend I’ve met. And I assume that he’s bringing a friends since he knew I was out with a friend. He buys first round, and then another drink for me. I REALLY appreciate that he doesn’t over do it on the drinking. But, I think it means I haven’t seen him really let loose yet. We have a good time, chatting, people watching. I find out that this friend is the roommate. I always feel weird asking people lots of questions. Mostly, because I don’t want to seem intrusive. So, it was nice that my friend could ask a bunch of questions, and its ok because she’s new to the situation.

Dimples takes leave to go to the bathroom, and his roommate asks me how I met him. Uh, didn’t your friend tell you? He said he forgot. Finally he says, you met at his work right? So, I admit that I basically slipped him my number. I jokingly asked what were all his secrets, but was told there was nothing. That Dimples is a very “what you see is what you get” kind of guy. Well great! That is not helpful at all! Because what I see and what I get is confusing. STILL. I haven’t had the chance to talk to him.

As the night goes on, two more friends join up. Then last call. He goes to give me a hug, so I stand up and face him. I’m facing away from his friends, and he gives me a couple little quick kisses. He tells me he is looking forward to Friday. I basically threatened his life if he cancels. Maybe more than once. I am so awkward sometimes.

Walking away I am wondering – Is he just that shy? Does he not like PDAs? Is he just not an overly affectionate guy? Was it a big deal that I met his friends? A guy that is not into me would stop hanging out with me right? And the fact that he kissed me at all in front of his friends must mean he IS into me?

And the most important question – SINCE WHEN AM I BACK IN HIGH SCHOOL?!

Which is exactly what this feels like at this point. The cute guy that is kinda sorta flirting with you, but nether of you push it forward. Then I realize – he kind of looks like one of my high school crushes. This can’t be a good sign.

Back to THIS Friday. I have a date to go paddle boarding which sounds like tons of fun. So I suggested it. Now I am realizing that I am an idiot. There is so much prep-work to being seen in a bikini by a guy (who I know will probably not even be paying attention). So, of course, I’ve gone out and now have a new bikini, and rash guard. I got waxed. I’m using sunless tanning lotion. Its all so much more work than I expected. I know we will have a good time. And its something I’m pretty sure we will both be bad at – so yay bonding experience!

You know how after the fact you run through the situation a million times trying to figure out what you should have said? Well that’s where I am now – but before the conversation. I feel the anxiety of the conversation that I feel needs to happen, but I have no idea HOW to bring it up, or what to say.

Wish me luck for Friday!



One thought on “Tour Guide

  1. LUCK!!! SO the overall message I get “from him” through this post, is a positive one in regards to “what the hell is going on?!” So that’s good. Maybe he IS just shy… all the misgivings you have about why he would want to hang out with you, maybe he has those exact misgivings himself, about why you would want to hang with HIM! You just never know. I’m glad there was some kissing, but I wouldn’t read TOO much into what that means, I’d just be glad I finally got a signal that he wasn’t just thinking we were buddies…. that’s all you should read into that. We read into SO MUCH that men never even give to seconds thought to…. it gets us into trouble. LOL

    And paddle boarding…. have you never been? It is SO MUCH FUN, but you are right, it’s going to be awkward maybe…. but remember guys don’t really notice all the things we THINK they are going to notice. Like if you have to climb back up on the board from a place you cannot touch bottom? That is the hardest part. It is NOT pretty. Don’t worry about that. Just have a good time. I do know that men enjoy women who DON’T seem so self conscious about everything and just enjoy the moments.


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