The School Administrator

It seems like time is going too fast these days and I never have enough time to sit down anymore and just reflect on how things are going. Particularly, when it comes to the dates I’ve had recently, I’ve just had to fly through them without having the luxury of summertime to sit and ponder for very long. So, to get back into the swing of things, let me tell you a little about the last two dates I had over this past weekend.

First, there was the school administrator. He has long, curly black hair and fierce eyes that are a dark brown almost black color. He is fairly slight in build. I know that he plays guitar and is about the same age as I am. Beyond that, there are a lot of unknowns. For this reason and also because I’ve learned some good lessons as I’ve been doing this online dating thing, I have us meet at a coffee shop not too far from where I live. He’s there a little before me so when I arrive I see him sitting at a table. I can recognize him right away. There is something about his energy that is intense.

For a good 15 or 20 minutes, we sit and talk at the table without ordering anything to drink. Eventually, I find a break in the conversation enough to make the announcement that I plan to order a drink. He follows me to the counter. There seems to be an unspoken agreement that I will at least be paying for my own drink if not his as well. The barista forces me to clarify this as he asks me if I’ll be paying separate or together.

A time ago, I never would have thought twice about paying my own way, but now I’ve come to find that the guys who are willing and able to foot the bill (at least for the first date or two) are a little more considerate and mannerly in general. They open doors and give compliments and sweet goodbye kisses. Somehow, I think they will be better partners for me and less selfish than the non-payers. Who knows if this is true, and I try to keep an open mind. I’ve never minded paying for myself before and certainly love to be independent, so this tide could turn. For now, it is one more element that puts question marks in my head about this guy.

We continue to talk and he asks me a pretty personal question about my dating history. I am nervous about answering this question, so my response is way too long and way too honest. I’m embarrassed and then relieved when he gets up to go to the bathroom.

When he comes back, I return the favor and ask him to answer his own question. He tells me it was never that important to him to find a lifelong partner and he tops it off by saying that he’s never had any trouble finding women to be interested in him. The little me inside giggles and thinks to herself, “good, then he won’t have a problem if this girl isn’t interested…”

Soon after, I make moves to hit the road and he walks me to my bike. He tells me something like, “You are the type of girl I really like. You’re nice to look at and I’d like to go out again. Would you like to go out again with me?” There’s already something inside of me that is gently speaking, “no, I sure don’t,” but I don’t know how to express this having felt put on the spot. So, I say, “yes”. I think he could tell something was off about my response because he said, “really?” But, again I said “sure”.

At the time, I was thinking, ‘why not? He’s an interesting guy to get to know.’ In reality, I already knew I didn’t want to date him, and as much as it would be fun to have another friend, our connection was off-kilter enough that it would have been too much work even for that. I haven’t heard from him, so perhaps we are on the same page.

The Entrepreneur

I’m on a second date with the entrepreneur. I don’t know how to describe his job exactly. He works for himself and owns a company that somehow runs itself and makes him a lot of money without him having to do much work. It’s still inexplicable to me and reminds me of the plan that the guys in “Office Space” hatch to skim a few cents off of every dollar and become rich overnight. Anyways, however he does it, he is able to simply bring his laptop with him and go mountain biking or hiking everyday and do a bit of work from the side of the trail. Hearing this, I try to remember how much I love my job. Still, I think I would love his job just a little bit more.

He gets a lot of points for thinking of something really unique and fun to do. We meet at a place called, “Cocktails and Canvass”. He’s there a few minutes before me and has already purchased two bottles of wine (a red and a white because he didn’t know which I’d prefer). I try some of the red since it’s open and I’m so starving from having not eaten all day. We receive a demonstration from an instructor on how to paint a specific picture. Then, with the paint and canvass provided, we follow her lead- step-by-step-until we each have a painting of our own. It’s a fun and flirty way for us to get to know each other a little better, and having this other thing to focus on takes some of the pressure off. The two glasses of wine on an empty stomach may have helped as well.

After painting, we go to a very nice Italian restaurant down the street. It’s late and the kitchen is nearly closed, so we order soup, salad, and a meat and cheese plate. The conversation gets better and better as the night progresses. He’s able to relate really well to my experience in the Peace Corps because he had similar life-changing experiences in the army and living in Kuwait.

I appreciate that Mr. Entrepreneur seems to have come from a similar background to me. I like that he has learned to enjoy and appreciate each day he’s given. He seems to have a genuine optimistic and kind nature. His family and friends mean a lot to him just like mine do to me. He is a sports nut and I can totally see him getting along great with my brothers, which is kind of a good litmus test.

I have felt at-ease with him while still feeling stimulated at the same time. At the end of the evening, he’s a perfect gentleman and asks permission to steal a kiss. I’m glad he did. We have another date scheduled to go hiking this weekend.