Can I just say something? In the world of modern dating, it seems like the concept of courting or pursuing a woman has become simply an urban myth that we read about in early 2000s romance novels. How many actual dates have you gone on, as opposed to a guy you swiped for hitting you up after you match on an app saying, “Come over,” “Let’s kick it,” or some really lazy approach to seeing you? It shows the intent, which is a metaphor for how a man feels for you.
What happened to a man making plans with a woman (in advance) to go to dinner, a movie, or even a museum! Jesus, how about going for a walk and grabbing food after. I’ll even accept a coffee date. What happened to showing a woman you want to actually pursue her and, afterward, planning the next date? It doesn’t have to be anything crazy or fancy…just thoughtful. It seems like the ones that do plan a first date, use all their party tricks on day one and don’t know how to plan the next. Is it because we all have so much at our fingertips that men have too many options right in front of them? You can say it’s the kind of guys I’m hanging out with, but I’ve dated a variety of men — I’ve dated wealthy guys, non-wealthy guys, young ones, old ones, successful, bums, addicts, sober, all different religions…they’re all the same.
Reflecting on my list of dates I’ve gone on, and the men I have spent time with, I decided to share my top five favorite dates I’ve gone on and why I thought they were the perfect date.
5. A Caviar Daydream with the Silver Fox
Starting the top five countdown was my date in Beverly Hills with an older gentleman, we know each other because we frequent the same spots in town. This was during a phase when I was into older guys. But honestly, we had so much fun. He picked me up in the hotel car, a Rolls Royce, we went to Catch Steak, ate amazing food, and did caviar bumps (my fave). I’m not a tequila person, but whatever the tequila was that we drank was chef’s kiss. This was the first older guy I’d ever dated. Honestly, he had such a young spirit, that I couldn’t feel the significant age gap.
Then we went back to the hotel where we smoked cigars outside in our own private area. The thing about the Silver Fox was, he was so established and successful, that everywhere we went, we were treated like royalty. The next day he took me to another steakhouse. We ended up staying friends.
4. Midnight Listings with my Airbnb Host
One of my favorite dates I went on was with my Airbnb host while I was staying at an Airbnb between apartments (we love a Jewish boy in real estate). I was looking for a new apartment in LA and wasn’t having any luck, so I found an Airbnb rental temporarily. Long story short, while I was staying at this Airbnb, I was looking for a place and I called on a “for lease” sign that I saw in the area for a condo and, coincidentally, it ended up being my Airbnb host’s listing. We got to talking and we ended up hanging out. He came over earlier in the evening, and we got espresso martinis and sushi. Honestly, it didn’t even start as a date, but he was driving me around at, like, 1 AM, looking at his different listings because he knew I was trying to find a place to live, and he had access to these spots. He ended up driving me through the flats in Beverly Hills, not that I could afford them, but they were just fun to look at (and let a girl dream). He had one listing in there with another very well-known real estate agent/reality star.
“Want to check it out?” he asked. I wasn’t going to say no, obviously.
We went inside, it was a beautiful home right on Santa Monica and Beverly. It reminded me of Cameron Diaz’s house in the movie The Holiday. It was my dream home, the vibe was very LA.
At this point, it was probably 2 AM. He gave me a full tour and we ended up sitting on the white couch that sat adjacent to the piano and two yellow chairs. Before I knew it, we were making out. There was just something so spontaneous about the whole thing, making out with my Airbnb host in my dream home in the flats. Very memorable. We had a little fling for a minute, but I didn’t end up with the dream house or him.
3. Malibu Beach Day with a Nepo Baby
Next on my top dates is actually a date I talked about in the last issue of Love, Sex, LA. I met this guy on Raya, and he came from a very prominent family in the entertainment industry — nepo baby at its finest. If you don’t know, a “nepo baby” is someone born into a famous family. I coined him as “The Star” in my last issue. On one of our dates, he invited me to the family beach house, where he brought wine and we laid out by the water, drinking wine straight from the bottle. It was like something out of a movie. But then he convinced me to get in the water with him…mind you, I didn’t bring a bathing suit, so all I had was the little black dress I wore. He tried convincing me to go skinny dipping, but there was no way I was doing that in the middle of the day at a public beach, even if there was no one there.
But nepo baby took me by the hand, and we ran into the freezing cold water together, me fully dressed and him in his bathing suit.
There was something liberating about the whole thing. After diving into nature’s own cold plunge, we hurried to the outdoor shower that sat in the courtyard of the front of the house, still fully dressed, and underneath the hot water, he took my face in his palms and kissed me. The whole afternoon felt romantic, like something I would’ve written. And there was something about the Star that was just so sweet. He didn’t make me question anything or wonder about what we were…at least at the time.
2. The Polo Lounge & a Comedy Show with LA’s favorite Entertainer
This date was truly one of a kind. I went out with this guy who is a well-known celebrity known for a very cool show he originally put on in Vegas but made its way to LA. After going back and forth all day about meeting up, we finally met at the Polo Lounge at the Beverly Hills Hotel for dinner. We both got espresso martinis — his with tequila, mine with vodka — and got to know each other. We had really good, witty banter between us. After the Polo Lounge, he invited me to a comedy show because his very high-profile comedian friend (you’ve seen him on almost every comedy roast) was performing. So we went to The Comedy Store, right on Sunset, and of course, even though we were in the back, his comedian friend picked on us because he saw us sitting in the crowd. After the comedian friend was off the stage, we went through the kitchen of the venue and met him in the back.
We didn’t stay too long before we decided to go to the members-only bar, Bird Streets, right down the road. It was my first time there and it was such a vibe. The entire rooftop was empty, so we had it to ourselves, he even joked that he had rented the whole place out for me.
We sat at the desolate rooftop, with an entire view of Los Angeles, and made out. And by the end of the night, he asked me the same question every guy asks me, “How are you single?”
Honestly, it is very much by choice. I have such a great life, that if anyone else is going to get involved in it, they have to make it even better.
The night ended, and he invited me to a very famous director’s house for Thanksgiving the next day, but I ended up traveling to Arizona to be with my family for the holiday.
Overall, this was such an exciting date because it was so much fun, and spontaneous, and I loved the way he wanted to make the night so special. There was thought and effort put into it. And who doesn’t love a filet from the Polo Lounge?
1. Day into Night with the Storm
The top favorite date I’ve been on was less of a date and more of an entire day & night spent together. Obviously, this was with the Storm, who I’ve written about in my last four issues of Love, Sex, LA. I think a lot of the time what makes a date so amazing is who it is spent with, and when you have a deep connection with someone, you can literally be doing nothing and it feels exciting.
I had spent the night at his house in Hermosa Beach which sat right on the boardwalk. The next day, he was having an open house and invited me to stay. So, I hung out with him, while people walked in and out and he showed them the home. I think it was probably hard for him because it had been a house in his family for generations.
After the open house ended, we drove around looking at houses for him in Playa Del Rey, El Segundo, Venice, and Santa Monica. While in Santa Monica, the sun just setting over the water, we got Thai food at this little hole in the wall right on Main Street. His friends called him and invited him out to a birthday party at a ’70s-themed bar in Hollywood. We met up with his friends first at one of their apartments right on Sunset, and being that the Storm was sober, he drove everyone in his Bronco to the bar. There was live music, and we danced the night away, him sober and me tipsy on tequila.
That night, he came back to my place and spent the night. What made this date so special was the energy we had between us. It was the connection. Like electricity. We had spent every day together leading up to that night. And I had just enough tequila in me while we were lying in bed to say to him, “Can I tell you something without it being weird?”
“Sure.”
“I think I’m in love with you.”
“I don’t think that’s weird.”
In that moment, I felt it in my heart and gut that he felt the same way. I knew my confession meant something to him, even if the words weren’t spoken aloud. I blame the tequila.
Anyway, I think what makes a date so special is always the connection you have with the person. Because I’ve been on some pretty spectacular dates with some of the most successful guys you can think of, and what stuck out to me with the top dates I listed was how I felt with the person.
It’s not about the fanciest restaurant or the most exotic location. It’s about those little moments when you feel truly seen and heard. When the conversation flows effortlessly and you find yourself laughing without even realizing it. Those are the dates that linger in your memory long after they’ve ended. The art of dating is about the effort, and someone making you feel special, not the location or the time of day. It’s about effort and intention.