Ongoing saga of my dating life...featuring a situation I never thought I'd encounter in my 30s. Also, this post is way too long.

Original nickname: 

"The Geek"

Smart, easy to talk to, funny. And also definitely a geek. 

The situation:

First date - not attracted to him, but had fun. Continued to enjoy his company over dates 2-5, but there was minimal touching, flirting. This is mostly ok - online dating means you're getting to know this person that you met out of nowhere, so it can take time to build a report and trust, etc. Still, the lack of any sort of non-friend interaction isn't really that normal - and I feel like I've given him plenty of opportunities to give it a shot. So, date #5 ended with a friend-esque kiss on the lips, then me trying to kiss him again and it was this sort of mostly closed-mouth nothing. He said, "That was nice." I hopped on my bicycle and sped the hell out of there, confused as hell.

(And, I also mention kissing - as in "you should be a great kisser" - in my profile.)

Still, having fun. And I would like to date someone who's really into me.

Decided to go out again - kind of one last shot. By now, I've already formed this picture in my mind of how he's not just very shy, but also really inexperienced and have changed his nickname to "The 35 Year Old Virgin." But, I am optimistic that he just needs to feel more comfortable and if nothing else, either I'll make a move, or just bring it up and talk about how this is moving towards a friendship.

It's a beautiful, unusually warm summery day in the city. We meet up Sunday. Tentative plans to go to a free concert in the park. Last minute, I say that we should bike out to the beach if the concert's not great. 

He shows up and the first thing - his bike helmet is too small or not on straight or something. His white athletic socks are sticking up strangely from his bike shoes and...anyway, his geekness is showing Big Time. I have, on the other hand, decided to wear my shortest sundress and bikini. I think the picture text I sent to G$ said something like "Hi. These are my legs. Will you kiss me, already?" The concert has a long, long line and doesn't look very appealing, so we head out to the beach.

Long walk, talking, laying on a blanket that I brought. Played a little paddle ball (That I also brought - and we both sucked at.).

Walk back towards our bikes. I'm searching for the right way to go, which means I'm being quiet. Then, towards the end of our walk, I finally Bring Shit Up. Express my thoughts about how this feels like it is entering The Friend Zone, but could still go either way for me. He understands. He likes me. And he's not really experienced with dating. Hm. 

Ooookay, it's still a really nice evening and I'm still on the fence. Let's go to dinner. We roll over to BStar, the relatively new cafe associated with Burma Superstar. Dinner is awesome. Then on to Q for dessert - hot chocolate chip cookies w/milk. I am pretty much the best seat-of-the-pants date planner of all time. 

It's just too bad that he doesn't know what he's working with. Le sigh.

Ride back, I go to where we're going to split up, ask him to pull his bike over, take off his helmet. I go in for a kiss.

And it is awkward. So much so that I say, "Wow. That was awkward." He agrees and then says that he's not really experienced. 

Let's review. I tried to kiss him and it did not work and it's because he's inexperienced?!? As the conversation progresses a little and I sort of press him for a little more on this and he doesn't provide much information, it becomes clear to me that I was not that far off on nickname #2. As in, my error was that he's actually 34 years old.

He's like, yeah, I get it if that's not going to work out for you. I'm pretty much clueless. Oh, and by the way, I go to church too. That's a deal-breaker for some people. But, this is who I am and I've got a lot of other great stuff going on, just don't have experience with girls.

Now I feel like a huuuuge bitch. And this shouldn't be an issue. And I don't really feel like I'm being fair. I mean, I have fun with this guy... but... yeah, it's an Issue.

The outcome:

So I didn't drop him, but I did let him know this unexpected and a lot to figure out. We talked about seeing each other again. 

But the more I think about it... I think that we're in really different places - physical stuff aside, he's just getting started with dating and I've lived with a partner. I've been dating fairly steadily since I was 16. That's 16 years of experience to his... um, not much at all. Not a very even starting line. 

And then you add the physical stuff. 

Well, I feel kind of like a horrible person. Kind of like I need to specify that I would like to date a man and not a boy. Overall...once again, it turns into a story.