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As you can tell from the title, last night’s first date with Boston was a success! We had a blast the entire evening, from the minute we first met at the bar to several hours later when I left his hotel.

We had initially agreed to meet at Bar Basic in SOMA at 6:30. He chose the spot because it was right around the corner from the restaurant, Cockscomb, where he wanted to have dinner if our drink meet went well.

Earlier yesterday I told him I would be arriving at the bar quite a bit early in order to save about an hour of commute time. He said he wouldn’t be able to arrive any earlier than 6:15 but that he’d do his best.

I arrived at the bar at 5:45, ordered a glass of pinot noir, and entertained myself while I waited for him to arrive. I was wearing dark blue jeans, navy blue long-sleeved blouse, and leopard print lace-up flats.

He lives in Boston but travels most of the month, including to San Francisco once or twice per month. I have a fairly strict dating policy about dating only locals but I made an exception for him because of his frequent visits.

And he’s age-appropriate!

Name: Boston

Met on: OkCupid

43 years old, medical entrepreneur, separated, 2 kids

Boston arrived at 6:20. He was very attractive with clear blue eyes, straight white teeth, and a nice smile. We immediately hit it off and had great conversation, like we were long-time friends.

He ordered a margarita. He was animated and had an almost nervous energy… leg bouncing, toe tapping. I commented on it, joking that I felt really calm next to him, and he said he’s always high-energy.

As I got to know more about him, I realized he was loaded. I loved that he wasn’t flashy about it. I learned that he used to be a general practitioner doctor but switched to starting medical technology companies 12 years ago.

The only thing he was reluctant to discuss was his family life, claiming it’s currently a difficult topic. He and his wife have been separated for a year and will be filing for divorce soon. He says it was an amicable split but that it may become hostile as they move forward. All he would divulge about his kids are their ages; they’re close in age to mine.

After we’d finished our drinks, he asked if I was read for dinner. Oh, so I made the dinner cut! I joked with him about that. He told me that I was his 2nd OkCupid date and that the date he’d had before meeting me was a disaster. She claimed she was 42 in her profile but was clearly in her upper 50s/low 60s. He was stunned. I asked him if she’d used old photos and he said, “Actually, I don’t think they were photos of her at all!” Yikes. He ended the date after they’d had one drink.

He’s frustrated with OkCupid. He said that he’d had many conversations but ultimately decided that none were worth meeting. He said red flags would come up in conversation and he wouldn’t pursue any further.

Then he found me. He said my communications were like a breath of fresh air and he was truly excited to meet me.

He paid the tab then we walked hand-in-hand to the restaurant for our dinner reservations. We were seated side-by-side at one of the best seats in the restaurant: at the bar overlooking the kitchen.

The restaurant smelled divine. Boston was excited; he’s a huge foodie. He told me the story about how he’d stumbled upon the restaurant as he and a buddy were on their way to see Dave Matthews in concert as part of the Superbowl festivities two years ago.

He brought a special bottle of wine from his home wine cellar for us to enjoy with dinner… an amazing French red! I swooned. He said he’d called ahead to make sure it was okay with the restaurant.

He pointed out all the items on the menu that he loved, saying he highly recommended the bacon chop or the hamburger with the sizzled egg and foie gras add-ons. I had a hard time deciding between the two but ultimately decided on the bacon chop: a large pork chop surrounded by a slab of bacon. Boston opted for the corvino. He also ordered a dozen oysters and the duck fat cauliflower for us to share.

Holy shit. The food was amazing! Everything was decadent and lovely. The wine he’d brought was incredible as well.

Our server, who was from Florence, Italy was so sweet and friendly. Boston even offered her a glass of wine but she couldn’t accept it, saying she was tempted but that she’d get in trouble.

We had so much fun laughing and talking throughout dinner. I told him things I don’t normally divulge on first dates. I felt comfortable and safe around him. And I was being completely honest without screening my thoughts. I told him why I made a dating exception for him. I told him that I don’t usually like knowing what someone is looking for because it’s impossible to know how things will change over time. He agreed.

He was complimentary but not overly so. When he told me how beautiful I was at one point, I stammered a little. He said, “Why do you act like you’ve never heard that before? I’m sure you get told that often.” I told him I’m still unused to it and explained how I was nearly invisible in my marriage. My husband never looked at me, let alone complimented me. Also, I explained that most guys aren’t very complimentary. He responded, “Really?! Most guys are complete idiots then.”

Boston is kind and genuine. This guy seemed to have it all and I felt lucky and honored to be sharing the evening with him.

He kissed me a couple times during dinner. I felt butterflies.

After we’d finished dinner, we were offered dessert. My eyes must have lit up. Boston said, “I’m not a dessert person but you apparently are so get whatever you’d like.” I decided on the chocolate pudding… and it was off-the-hook. It came with whipped cream and black salt sprinkles plus a divine cookie wafer. I ate the entire thing.

As we left the restaurant, he asked what we should do next and added, “I have some champagne chilling back at my hotel if you’d like to join me there.” Yes, of course! I teased him by saying, “Oooo, were you expecting me to come back to your hotel with you tonight?!” He replied of course not, but that you never know.

We got an Uber to the hotel. He had a room on the 32nd floor. The view was spectacular. I stood at the floor-length window marveling at the city lights while he opened the champagne. We toasted to finally meeting each other, then soon one thing led to another.

He had divulged during dinner that he loved providing oral pleasure and now that we were back at the hotel room, he wanted to get straight to that. He told me, “I want you to have at least one orgasm before we move onto anything else.” He succeeded.

I told him I wanted him to fuck me and laughed when he pulled a condom from his bedside table. He was prepared! And then I moved to get the lube from my purse. He teased, “Oh! Look who’s being presumptuous now! You packed lube.” I laughed and explained, like him, that you just never know….

I also explained my latex sensitivity and that I hoped it would reduce any latex trauma.

I climaxed another couple times during intercourse and apparently yelled so loudly that I irritated my vocal chords. Before long he wanted to go down on me again. He told me to sit on his face. I did, while holding onto the bed’s headboard. Admittedly, this was the first time I’d ever sat on anyone’s face. It must have been the magic position for me.

Because it happened. I squirted.

It didn’t even register at first because I was so in the moment. Afterward, he said, “You squirted! It was so fucking awesome. That was so hot!”

I said, “Oh, so that’s what that was! That was the first time it’s happened. I didn’t even know I could!”

Wow. I can’t believe it and wonder if I’ll be able to achieve it again.

After that, I gave him a blowjob and he came everywhere. We laid cuddling for a bit, until he mentioned that the cum was starting to drip down the sides of his belly. Even though he protested, I jumped up to fetch a hand towel from the bathroom.

He had to be up for an early flight so we had to say goodbye. He waited with me for my Uber and told me to text him when I got home.

As I was walking into my house, I got a text from him asking if I was home yet. I replied, “I just made it home. Ugh, I drank too much. Not a fun ride. Sweet dreams, Boston. Thank you once again for an incredible night.”

He replied, “You too. Glad you’re home. Awesome evening for sure!”

I ripped off my clothes and fell into bed without even washing my face or brushing my teeth. I never do that!

I immediately passed out and woke up at 5:30. I got up to wash my face, brush my teeth, take 2 Advil to circumvent hangover, and guzzled water. As I was laying in bed reminiscing about my amazing night, I received a text from Boston at 6:15 saying, “I slept very well last night I must admit. I hope you have a great day!”


I also had a message on OKC from tonight’s date confirming our dinner plans. I went online to respond to him and noticed that Boston had already removed his OKC profile. He had told me that he was going to delete it seeing as our date was a clear success… but I was surprised he had done it so quickly.

I like Boston and am glad I met him. Being that we live on opposite coasts, there’s clearly not a long-term serious future for us. But I think it’s pretty amazing that I may have found someone who will wine and dine me and make me feel really special whenever he’s in town on business.

Tonight: Another first date. We have dinner reservations at 6:30. Details coming tomorrow!