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I had my 2nd date with Attorney Guitar Dad (AGD) last night. One word: fabulous!

He called me yesterday morning to work out the details. He said he wasn’t sure he could make it to my office to pick me up when I got off work and instead suggested meeting a couple neighborhoods closer to him to buy him some time.

I told him that was fine.

We met at Rockridge BART station in Oakland at 5 pm. He pulled in not long after I arrived. I got in the car and gave him a hug. He looked even cuter than I remembered: dark eyes, adorable dark hair with some salt & pepper gray, and a sweet dimpled smile. It occurred to me that he resembles Justin Trudeau, who I have a bit of a crush on.



Justin Trudeau


He asked if I wanted to go to a tiki bar in nearby Piedmont. Hell yes!

We talked nonstop while sipping tiki-themed cocktails and beer. He did his fair share of asking questions, which I loved.

It was apparent he was really inexperienced at dating. He met his ex-wife in college. They married in their mid-twenties and were married for 20 years. He’s had one serious relationship since they separated 3 years ago. (She was a friend who was also going through a separation.) I was the first person he’d met online… and the first person he’d gone on a date with since splitting from his ex-girlfriend.

He told me he wanted a break from the heartache. I could be wrong, but I read between the lines to take that to mean he didn’t want to get himself into a serious relationship again anytime soon.

It’s apparent he’s a relationship person like me, though.

After a couple drinks, we headed across the street to an Italian restaurant & bar. We sat at the bar and shared an antipasto plate plus more cocktails. He had a Sazerac, I had a grapefruit gimlet. Sitting next to him at the bar was nice. He’d occasionally touch my leg or arm.

I offered to pay for the antipasto and cocktails since he’d paid for our tiki drinks plus lunch earlier this week. He wouldn’t hear of it. When I balked, he said, “No, just deal with it.” Haha. Okay then. I loved that he was insisting.

After finishing up there, we headed back to the tiki bar because he’d remembered he’d left his tab open. We opted to stay and have another cocktail. Of course, he insisted on paying again.

Eventually, it was time to call it a night. We’d had a 6 hour date by that point and I was loving every minute. He asked if he could drive me back to San Francisco. What what?! I was impressed. What a gentleman!

Once at my place, I asked him if he’d like to come inside. Luckily, he agreed. I wasn’t ready to say goodnight.

I gave him a tour, poured us some seltzer, and we settled onto the couch. We talked for about another half-hour before he leaned in to kiss me. Things got heated quickly after that.

We tore our clothes off and then moved into the bedroom. Factors such as dryness despite plenty of lube (I had just finished my period), the condom, and his large cock size made it a little uncomfortable and I got torn up pretty significantly. I did manage to climax, though.

He asked if he could stay overnight. I was happy he asked! We slept spooned together all night. It was blissful. He’s an awesome snuggler and I told him so. He made a joke about editing his profile to say: “I have no soul left… but I’m good at cuddling.”

He did say that he hadn’t logged into OK Cupid for several days, though. I didn’t know what to make of that.

When we woke up around 7, we continued the sexual fun until he had to leave at 9. A friend was helping him haul stuff to the dump so he had to hurry home.

I walked him to the front door and kissed him goodbye.

I like him. A lot. And I feel a little off-kilter because of it. I’m feeling like a fish out of water, floundering. I would obviously want to try out a relationship with him… but I think he needs to date just to see what else is out there. Does he even know what he really wants?

I hope we can work it out.