Date #101 - Last, But Certainly Not Least

His Age: 46
His City: San Francisco
Setting: “Writers With Drinks” at the Make-Out Room, Doc’s Clock, and The Beast & The Hare -- Mission district, San Francisco.

Can we have a little appreciation and acknowledgement for what I just accomplished, people? I completed what seemed to be impossible – 101 first dates. And this one was definitely worthy of my time and attention.

Our date was set for my favorite event, “Writers With Drinks” at the Make-Out Room. You might consider it a test date. If a man can’t hang here, he probably isn’t going to be able to hang with me. The writers are irreverent, bold, edgy, and usually read their books on sex, BDSM, or lesbianism, and sometimes on lesbian BDSM sex, in the case of this evening.

On 22nd street, in front of the old marquee, I stalled to read his texts to see he was already inside, had covered my admission into the club, and had secured two seats. A minute later, a new text: “You’ll be able to spot me easily – I’m the one with the jitters.” Learning this new information began to calm my trembling hands and wobbly legs. How could this be? How could I be so nervous? I just had to remind myself, I’ve done this before (100 times already).

I spotted him holding our two coveted barstools – cute! He quickly bought me a drink, and for the first few minutes he was unnaturally quiet – it was nerves. Sweet. We both relaxed pretty quickly and started exchanging stories before the show started. I found him smart, insightful, interesting and really funny. We both laughed at the same things when often other people didn’t – always a good sign.

He looks like Hugh Laurie, my go-to crush. He is so my type I considered not even attempting a date – chemistry is like crack, after all. My saving grace is he doesn’t sound or act like Hugh or, more importantly, his character, Dr. Gregory House. Having his very own personality gave me a shot at being myself instead of some odd and contorted version of something that might resemble me.

His formative years were spent in New Jersey, which gives him an accent. It’s slight, until he gets animated in storytelling, at which point it fills out. Then he talks about this mother and I wonder if I’m not sitting in her kitchen in Hoboken.

As the show wrapped up, I made quick introductions to old friends of mine, one of which was the bar owner. And I got to say “hi” to the world’s most adorable MC, Charlie Jane, also a highlight. And as everyone poured out of the club, we realized we weren’t done with each other - not quite yet.

Our next stop, Doc’s Clock. A woman looking much like Susan Sarandon’s twin sister with a little bit of Shelly Long thrown in for good measure asked what she could get us to drink to start us on what turned out to be the storytelling portion of the evening.

As we’d stumble onto taboo topics I’d get tentative and back off. Finally, he told me to knock it off – to trust him. That maybe, just maybe he wouldn’t judge me for what I wasn’t saying. So I went for it, often. We had all kinds of treacherous first-date conversations that should have killed any potential for a second date, and it all turned out just fine.

I feel safe with him. We talk, look into each other’s eyes, and kiss, then talk, look at each other, and kiss some more. We repeat this cycle several times. I love my life. Eventually, I look at my phone to check the time. It’s 1:30 AM. In horror, I realize the parking garage I used closed at midnight. BART stopped running at midnight as well.

“Can you drive me to my friend Melissa’s house? She has four children I’ll probably wake them all up. She won’t mind.” I say.

“I could, but I’d rather you stay with me. Don’t worry – we won’t have sex. I just want more time with you.”

What’s a girl to do?

In the morning, he told me I looked pretty without makeup. No one had ever said that to me. In that moment, it felt like one of the best compliments I’d ever gotten.

He was kind enough to lend me his red Converse sneakers, because I couldn’t bear putting on my knee-high, 6-inch-heel stripper boots for the “Walk of Shame,” which we renamed the “Walk of Pride,” on a Sunday morning. So in my short black dress, black tights and borrowed red Converse, I fit right into the Mission on a late Sunday morning.

After a tasty breakfast of chicken and waffles, he walked me to my car, kissed me goodbye and we parted ways.

Broken Rule #1: We discussed taboo topics I would normally save for much, much later: Things like I lead workshops about relationships and sex; I teach dating classes; he’s first date 101; I dance on a pole at the Power Exchange.

Broken Rule #2: I stayed the night at his house – on the first date (yes, I did). Hey – I was stuck! Don’t judge, and if you do, judge how pretty I look in the morning without any makeup.

P.S. An equally if not more successful second date has already taken place. I see a very nice little friendship here.