It’s official — the very first rendezvous in our new monthly dating series, The Sync Up, has happened. The 7.5-hour affair involved a helicopter ride, lunch at the Fairmont Hotel, and Netflix and chilling. That sounds like a successful romance in the making, but will it result in a second date for our debut couple?
To back up, if you missed the news, The Bold Italic is launching The Sync Up to bring a little bit of joy back to the San Francisco dating scene. For those who are tired of soul-sucking swiping and uninspired conversations over drinks, we’re presenting an alternative: let us set you up on a blind date and a wild adventure around the Bay and see where it leads.
After our announcement went live, we received an overwhelming number of applications (showing just how bad the city needs us!). Interested in participating? You can still apply here — we’ll be selecting people on an ongoing basis.
We here at TBI take our new matchmaking duties seriously.
The Couple
For our first date, we chose the following two folks:
Jared Markowitz
Age: 29
Occupation: Office manager for a coding bootcamp in SF
Time in the Bay Area: 2.5 years
Neighborhood/city: Castro
Interests: Reading fantasy books, cooking, watching movies and anime, wandering around the city in search of good cafes, and getting lost in forests
Michael Lau
Age: 28
Occupation: Graduate student at the University of California, Berkeley, and “love documentarian”
Time in the Bay Area: 5 years
Neighborhood/city: Berkeley
Interests: Hiking, scuba diving, rock climbing, dancing, drone flying, and revamping his friends’ dating profiles
Both self-described serial monogamists, Jared and Michael stood out as a potentially solid match in their applications on account of their shared sentiment that dating as a gay man in the Bay Area can be tough. In their experiences, they’ve mostly encountered men looking for hookups who aren’t necessarily interested in commitment. And they were both excited about the romance of The Sync Up and what a good meet-cute it could be.
“Everyone is afraid of committing to anything beyond sex. I think most people are just passing through, so they aren’t looking for anything long-term,” Jared wrote in his application.
“This seems like the start of a Hallmark movie. I’m in!” wrote Michael, who says he “absolutely loves” running his photography/videography business, in which he documents proposals, weddings, and other love moments. In addition, he has a side hobby of helping friends with their dating profiles and analyzing the Five Love Languages. “I’m deeply invested in my friends’ love lives to the point that I save my miles to use in case a friend decides to propose to their partner on short notice so I can be there to document their proposal,” he said.
These two were really adorable, and we couldn’t resist their romantic outlook on our new series, so we set them up on a fantasy blind date that came as close to the setup of The Bachelor as we could manage: a helicopter ride around the Bay Area with San Francisco Helicopters followed by an intimate lunch at the Fairmont Hotel, where they could open up to each other. Let’s see how it went.
The Date
Jared and Michael knew nothing about each other except for each other’s first names before meeting up on a cool Sunday morning. That meant they had no clue what the other one looked like. Both showed up at the Fairmont to be picked up for their helicopter ride with San Francisco Helicopters and waited for an awkwardly long time next to each other before eventually realizing who the other person was.
What were the implications of meeting someone and then jumping into a potentially dangerous situation? Would they bond with each other instantly?
Given that we’re all so accustomed to going on dates with people after stalking them and analyzing multiple photos of them online, the experience is understandable for this pair of millennials.
What did they first notice about each other?
“His shirt,” Jared said about Michael, who was dressed in a nice red and blue button-up shirt.
“His shirt,” Michael said about Jared, who was dressed in a more casual graphic T-shirt and a hoodie.
(Apparently, you should wear a shirt when you’re going on a blind date.)
Once the two introduced themselves, they hopped in a shuttle that would whisk them away to their helicopter adventure. What were the implications of meeting someone and then jumping into a potentially dangerous situation? Would they bond with each other instantly? We at TBI certainly hoped so.
But they weren’t alone. San Francisco Helicopters offers a variety of trip types. They were on the Vista Tour aboard a Bell Jet helicopter that glides over the hills of San Francisco and Alcatraz. The other riders included a couple from Ohio and a father and son from Denmark. Jared and Michael were embarrassed among the group when the shuttle driver called out, “There’s a couple here on a blind date! Who is it?” And everyone turned to stare at them when they raised their hands.
It turns out that they couldn’t do much talking or flirting in the helicopter since the group was hooked up to the same headset system. To avoid everyone hearing their “get to know you” questions, Jared and Michael opted for silence instead as the helicopter barreled down under the Golden Gate Bridge.
“It was perfectly fine, though,” Michael said. “Jared would tap me if there was something really cool to look at. I would tap him when there was really beautiful scenery or when we flew over the Castro, where he lives. We weren’t able to talk, but we were able to communicate in that way, and it was great.”
After the ride, the couple was dropped back off at the Fairmont, where they enjoyed a three-hour lunch in the Laurel Court Restaurant & Bar in the lobby of the iconic hotel. They both felt that they weren’t bougie enough to be there, but without their headsets or an audience, they were finally able to get to know each other more freely over their fancy lunch.
Michael revealed his hidden talent for understanding how people work. “I’m really into Myers-Briggs personality types — I love analyzing people’s personalities,” he told me later after the date. “So I casually asked him what his Meyers-Briggs was, and he told me he was an ENFJ, but I knew he was an ENFP.”
Jared said he felt the most connected during lunch. “As the date went on, I saw more of Michael’s personality. We talked about our dating history, and in the back of my head, I was thinking, ‘Oh no, you’re not supposed to talk about your past relationships on a first date,’ but we did…and actually, it was nice to understand where someone is coming from. That felt more vulnerable.”
Ah, vulnerable. Now we were reaching The Bachelor romance territory.
The two hopped from topic to topic during their conversation as they dined. They started with charcuterie and buffalo wings. For their entrees, Michael ordered the chicken and waffles, and Jared opted for the turkey and pesto sandwich. For dessert, they shared a chocolate mousse.
“We talked a lot about dating in the Bay Area and what it’s been like for us,” Michael said. “We also discussed our application to the date, the different responses we shared, and what we like to do in our free time. Jared is super into video games and anime; there’s this one game he really loves called All Hallow’s Eve or something. He’s also super into making bento boxes currently, and he likes to put everything in a little box for lunch.”
“We discussed the different dating apps we use,” Jared said. “Because he’s really into design, he likes Hinge the best.”
After lunch, the moment of truth. The date that we had planned was over. What was next?
Michael asked Jared what he was doing later that day.
“That made me think he wanted to hang out later, so I asked if he wanted to go to a dessert place in the Castro,” Jared said. “I asked if he minded if I stopped at my house first so I could take something for my headache, and then we ended up just staying there because we had actually just had dessert.”
Michael noticed that Jared’s apartment was pretty bare, shocked that there was only one succulent in the whole apartment. “And it didn’t look like it was doing too well,” he said.
The two had the house to themselves, as Jared’s roommate was in his room, giving them privacy. They decided to watch Aziz Ansari’s new Netflix special, Right Now, laughing at the funny parts and “awe-ing” when the episode turned more serious. For Michael, this was his favorite part of the date. They had flown in a helicopter under the Golden Gate Bridge and had had a fancy lunch, but this shared experience of watching Jared’s emotional reactions to the show did it for him.
When it was time for Michael to meet up with his friend, he hugged Jared goodbye. There was no kissing.
After the Date
So would they go out again together?
“Yes, I definitely would,” Jared told me in an interview after the date.
“Yeah, I would be open to going on another date with him,” Michael agreed.
But a few days later, I received an email from Michael that encapsulated an all-too-familiar experience: leaving a first date feeling positive, but after taking time to reflect and talk it over with friends, realizing that there is something nagging you that makes you rethink going on a second date.
Michael shared that while he had had a wonderful time on the date itself and that Jared was amazing, he felt that they had very different interests and wanted different things out of life. He also shared that Jared didn’t seem to have a genuine interest in understanding why he loved photography and videography so much.
Michael texted Jared to let him know his feelings.
“I said ‘OK,’ but on the inside, I was thinking, ‘How can you judge what someone wants out of life after one date? I’m not asking you to marry me. I’m asking you to hang out again because I had a good time, and I thought you did too,’” Jared said. “I know he thinks a lot about relationships and people and classifying them to understand them better. I kind of understand where he’s coming from, but it also seems like kind of a stressful way to live.”
Overall, both agreed that it was a superfun date. Jared appreciated Michael’s honesty, and even though Michael felt that Jared was a great, well-intentioned person, he concluded that they were just looking for different things.
We at TBI still deem this first date a success. Look out for our next Sync Up date next month!
Thanks to San Francisco Helicopters and the Fairmont for partnering with us on this date. Interested in our editorial team setting you up on your very own blind date for your chance to find love? Submit your application here.
