Preface: I've been travelling the country for a few weeks now teaching a few courses through my job. I had never been to this week's city (Oakland) and decided to fly into San Francisco a few days early to check out the area. I didn't realize I had no game plan until I landed.

--Friday--

I arrived at a 12-bunk hostel and while I was catching up on work this beautiful HB9 strolls in. Chatting her up I find out she's a dentist that's coming in for a conference in the weekend. We quickly realize that neither of us know anyone in this city or have any idea of what to do. Luckily, I had spent a few hours walking around and chatting up local restaurant staff and random folks on the street to figure out what I should do here (this is important).

So I suggest to the HB9 that we go for a stroll and check out some of the places I was told. As we're walking down the street, I continue to stop and chat up locals and ask them questions like what they like about SF and what's something we should check out. She seemed to be really impressed by my ability to approach strangers and strike up conversation. As we continue walking, a few people I had met earlier in the day recognized me and would wave, say hello, or ask my how my day was going so far (I'd like to say this was a demonstration of social proof).

We finally pick a bar and eat and get some drinks where the bartender gave us a very thorough run down of the city and I realized at this point I was onto something when she started asking me questions like, "how do you find time to date when you travel so much?". I initiated kino by touching her on the thigh (I was sitting next to her (but facing her with my legs and body open towards her) whenever we hit a positive note in conversation [example... Her: "This sandwich is so good!" // Me: places hand on thigh "I know! We should order another one!"]. She wasn't really reciprocating any of my advances but she wasn't really pulling away either (In hindsight, if a woman isn't reciprocating advances but isn't rejecting them either, You're in the clear!).

After the bar, we started heading back to our hostel and stopped at a wine bar where the atmosphere was a little bit more dimly lit and intimate. The conversation reflected the new setting as well. Some topics we talked about were:

  • What do you want out of life?
  • What makes you happy?
  • What were you like as a kid?
  • How did you know your career is what you wanted to do?
  • What's your dream home look like?

One cute thing we did at the wine bar was order a dessert to share and take the first bite crossing arms like this. The night concluded early as we both needed to wake up early but we agreed to hang out the next day.

--Saturday--

I drove up to Napa in the morning and came back around the same time she was finishing up her day. We started the night by getting dinner around the corner from where we were staying. After dinner I told her I've got a night full of adventure and she's more than welcome to tag along. After agreeing, I held out my arm and said, "Shall we?". She commented on how my 'arm and arm' form was great and I told her I walked my sister down the isle when she got married (DHV?).

We stop at a comedy show where the host stopped the show to call me out, "Thanks for coming brotha! I didn't think you were gonna come but I'm really glad you did. I thought you were gay but here you are with a beautiful woman on your arms. You must have a good job!". We laugh and sit through about 3 sets at which point I tell her we need to keep this adventure going.

We get in a car I rented (I opened the passenger door for her and she asked me if this was a date. I told her, "I'm not a fan of labels, Let's just go with the flow and have fun") and headed up to Twin Peaks, the highest point in SF that overlooks the entire city. I laid out a blanket and poured out two glasses of wine that I picked up from Napa earlier in the day. What I didn't realize that it would be fucking cold up there so after 10 minutes I suggested we go seek out some warmth, but before we do so.... kiss and I told her I had wanted to do that from the second I saw her.

We get back in the car and drive around SF aimlessly for about an hour and talk more about life / career / family before she asked me, "is this the part where we netflix and chill?" We head back to the hostel and watch a movie together. Afterwards she sends me a text saying "feel free to cuddle with me anytime between now and 7am.." needless to say, the rest is history.