The Time I Broke a Rule (and Why I’m Glad I Did)

o-DATING-RULES-DIVORCE-facebook I had a date on Saturday that would rank as one of my Top Five Favorite First Dates Ever. If you have read any of my other dating adventures, you’d know that this is A Big Deal.

It didn’t start out well–he lives an hour from me, which is no biggie, but I got lost. Google Maps kept telling me the restaurant was located in a tube/tunnel that connects Oakland to Alameda under the Bay, which is clearly impossible. I ended up being 40 minutes late. Plus, I had to park 10 minutes from where we were to meet. When I got there, he was gone.

So I called. “Hey, I’m here, where are you?”

Him: “I left.”

Me: “You left??”

Him: “Yeah, I left. You’re so late–that’s really rude of you to show up so late. So I left.”

Me: (fuming) “Wait – I TOLD you I wasn’t familiar with Oakland. Google Maps was all fucked up and kept telling me the restaurant was in the Webster tube, so I ended up in Alameda. Twice. It was tricky getting here, even trickier to park, I drove to YOU, and now you’re telling me . . .”

Him: “I’M KIDDING. Sienna, I’m kidding. Come outside the restaurant. I’m walking toward you right now.”

And he was. A tall, handsome smart ass with a big grin on his face and a beer in his hand was walking across a grassy area toward the restaurant, and I started walking toward him. Ready to punch him in the balls.

But the minute we met and leaned in to hug each other, chemistry, attraction or whatever the hell you want to call it kicked in . . . and my frustration, anger or whatever the hell you want to call it dissipated.

Woah. Immediate connection. Like a jolt of positive energy. I don’t know why or how or what happened in that hug, but I could tell this was going to be a great evening. And it was.

He was a smart ass to rival me, which I loved. He was witty and funny and charming and sweet. Adorable. Smart. Successful. Let me stop, because I could go on . . .

At the end of the evening I told him, “I wanna see you again.” He said, “Yeah,” and we parted ways.

And here’s where the part of dating that I hate the most kicks in: The After. According to “the rules,” as a woman, it was now my job to wait. Wait for him to text. Wait for him to call. Wait for him to ask me out again.

Wait, wait, wait . . . for what? To know if the chemistry was mutual? To know if we would have a second date? Waiting sucks. Especially when most of us know fairly soon after meeting someone if we’d like to see him again. I’m willing to bet that his mind was made up within 15 minutes of meeting me. I know mine was. So why can’t we all be adults, cut to the chase, and just say it?

The next day, I wrestled with the whole concept of waiting . . . of not wanting to appear too available or needy. I mean, I’m not those things. I don’t need to see him again soon. With my busy schedule, I’m not all that available. But damn it–I wanted to know. Right now. So I did it, my friends. I texted him first. Sunday afternoon, I sent him this:

“So I had a great time with you and I would love to see you again . . . but I think I told you that. I love hanging out with someone who’s as big of a smart ass as I am. I felt like we had a good connection, and I rarely feel that when I first meet someone . . . how about you? I hate trying to guess, and I really, really like being direct.”

Boom. Rule broken. Less than 10 minutes later, he sent this:

“I had a great time as well. Would love to see you again, yes.”

And that was it. I had my answer. I didn’t respond. I didn’t need a full-blown conversation. I didn’t need to know  the details of a second date. I was just satisfied to know that the feeling was mutual. And I decided, now the ball’s in his court, I’m comfortable with that and he can make the next move.


I didn’t play the game. I broke the rules. And I’ve decided this will be my new MO. Even if a second date never comes to fruition with this guy, I’m okay with that. At least I was honest, direct and I was exactly what I wish we all could be in this crazy, chaotic dance that we call dating: True to myself.

Dating would be so much less of a bitch if we could all just scrap the rules and get real with each other. I’m too busy for games and too stubborn to follow someone else’s rules for how my relationships should play out. So I think I’ll continue to shoot straight and follow my own rules.

Now. If Google Maps could get their shit together, life might get even more grand . . .



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  1. YES!!! Good for you!! I texted first after an amazing first meet-up and we’re living together. Rules are made to be broken!! 🙂

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