100 Emails, 20 Dates An SF girl's systematic quest to end her singlehood

Date 7: The setup, aka Present your best self | Baby Step #3

One piece of dating advice that I think is really, really true is to be yourself, but be a better version of yourself. This isn't to say that you should mask who you really are or pretend to be something you're not in order to make a good impression (thus setting yourself and your date up for disappointment when the real you inevitably reveals itself down the line. It's to be the best you, the good you, but still the real you.

Still not buying it? Let's use an analogy. Sometimes, on weekend mornings, I leave my house with bedhead. I don't put on makeup. I wear the jeans and t-shirt I wore to the bar last night and they may still smell faintly of beer or smoke. I can't tell, because I smell faintly of beer or smoke. That's three-months-in me.

When I go on a date, especially a first date, I make sure my hair looks like how I want it, not how it ended up that day. I reapply makeup. I wear something flattering. I don't make myself look like something I'm not, but I put my best foot forward, physically. Although that's not the real me everyday, that's the real me on my best days.

It only makes sense to put your best foot forward, personality-wise, too, right? So why is that so hard to do?

A friend fixed me up on a blind date a few weeks ago. "Before you meet him, I need to brief you on O.," she said. "He's very dry. For the first few weeks I knew him, I thought he hated me, because he just didn't talk. But now he's one of my dearest friends and he talks my ear off."

Armed with this information, I met him for a beer. She was right. He was very dry. Very. I was working very hard to get him to talk and to open up. He didn't ask me many follow-up questions when I would talk about myself and seemed uninterested in what I had to say. (He didn't even seem that impressed that I was in a band, and let's be honest, if I don't wow a guy with that, the "life history" bag of tricks" is pretty damn empty.)

So I kept asking him questions. I filled the silent spaces. I made him feel comfortable, or tried to. And at the end of the night, he asked if I wanted to hang out again. I said sure.

As I thought about it after, I felt frustrated that I was working so hard. I mean, come on! It's a first date! Ask the girl some questions! Is this a sign of what's to come if we date? Am I going to have to do all the work? And I kept coming back to my friend's warning. That's what made me agree to see him again, because to be honest, it was a fine evening, but it wasn't fun. But he was opening up toward the end, and he was a nice guy. So why not?

And then I realized that as much as he wasn't being the real him, I wasn't being the real me. I was appalled at my somewhat forced laughter that night. I'm normally fine with pauses in conversation. I emphasized parts of my life that normally, I would not emphasize. I wasn't my best self. I was an annoying first date self. That helped put it all in perspective for me. I wasn't just giving him a second chance; he was giving me a second chance.

So I hope I make some progress on this step in "date" #2 (it feels like too much pressure to call the "getting to know you" evenings dates). We'll see.