“Sydney Ellen Wade: [as they head to the state dinner] Do you do this often?

President Andrew Shepherd: Well, we had a state dinner for the prime minister of Japan, who died shortly thereafter, so we stopped having them just in case.

Sydney Ellen Wade: No. I mean, do you date often?

President Andrew Shepherd: Oh. No. You?

Sydney Ellen Wade: Yeah, well, lately I seem to be going out on a lot of first dates.”  – The American President

I’ve been doing a lot of first dates lately, too.  I’ll tell you a secret. I don’t love dating.  I especially don’t love first dates. I’m envious of people who think dating is fun. Of course, most of those people are in their twenties, when, indeed, dating IS fun.

Now, though, it’s – not a job, but not precisely fun.

For one thing, I’m awkward with dressing appropriately for the first date. I know, I know. Guys love the skirt or dress. The trouble is, a skirt or dress is almost always either a little too much or too work  or too casual for a first date.  All my dresses are dressier.  My skirts are either work appropriate or casual. There’s not much middle ground. So it’s stressful for me to find a cute, not-too-corporate, not-too-casual, not-too-dressy (and yes, there is such a thing) outfit for the first date.

And then there’s the conversation. One recent first date brought up politics on the first date. Really?  I tried to not engage, and keep things light, but it was obvious quite soon: we do not agree.  I did go on a second date with him.  We were talking about cooking and I mentioned that I don’t grill often because it’s a lot of effort (I was going to say for one person) – at which point he cut me off and said “for a girl?”. Which is a little funny, but…not.  I digress.  When the conversation is good, you discover some things you have in common- music you like, places you’ve visited, other random things you have in common. Interesting differences between the two of you.  But the kiss of death in first date conversation? Talking a lot about your jobs.  While jobs are a part of getting to know the other person, they’re generally not the main topic of conversation of any good first date I’ve had.

But the worst thing about (most) first dates? The disappointment. When you’ve hoped to be excited, you’re only meh. Where you’ve hoped for connection, you feel like you’re stuck making random conversation at a cocktail party where you know no one.  When you’ve wondered if this guy might have potential, and you’ve had a good time and all you get from him is “have a good evening.” No “I’ll call you.”

First dates- the things we do because some part of us believe- or want to believe- in love. Because no matter how bad the last first date was, we can’t help but hope the next one will be different.