The very first rendezvous in our new monthly dating series, The Sync Up, kicked off with a helicopter ride, but alas, it didn’t result in a second date. Would this month’s blind date be different?
Our latest date started with dinner and a bottle of wine and concluded with a couple’s-therapy session. Was it love at first sight? Lust at first sight? Did the session end with wine-fueled confessions about early childhood trauma and other issues?
First, to back up in case you missed the news, The Bold Italic launched the Sync Up earlier this year 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 an adventure around the Bay and see where it leads. After our announcement went live, we received an overwhelming number of applications (showing just how badly the city needs us). Interested? Submit your application here. We’re selecting dates on an ongoing basis.
We took the role of selecting our second couple very seriously, more determined than ever to have their date result in love. From our pool of qualified applicants we chose the following two folks:
Mark Mastrangelo
Age:
29
Occupation: Product manager
Time in the Bay Area: Two years
Neighborhood: Laurel Heights
Longest relationship: 3.5 years
Interests: Saturday-morning basketball, attending concerts (27 last year), a monthly dinner group with friends exploring bars and restaurants, writing
Eliza K.
Age:
33
Occupation: Health economist
Time in the Bay Area: Three years
Neighborhood: Lower Pacific Heights
Longest relationship: Three years
Interests: Wine tasting, hiking (followed by wine/beer), calling into Australian radio stations (where she’s from), snowboarding and après-ski, scuba diving
Eliza was tired of dates with boring guys who liked to mansplain financial advice to her on the first date, while Mark told us that dating in San Francisco was “great and terrible” at the same time, likening it to pretending to care about someone’s startup platform. Could two San Francisco dating pessimists fall in love?
Since we can’t resist a healthy challenge here at TBI, we decided to set them up. We thought that their active lifestyles, curiosity about exploring the city, and general down-ness to try new things meant that they’d have something to bond over instantly and could potentially result in building a kickass life together.
The couple knew nothing about one another, except Eliza knew that Mark would be wearing a red shirt. He was nervous about meeting a stranger without knowing what she looked like. After all, this is a time when we have extensively prescreened the people we meet through online dating by Googling their names and stalking their Twitter account back to 2010.
The two recognized each other outside modern Greek restaurant Souvla on Chestnut Street and immediately hit it off by joking about the experience they were about to have—dinner, then couples therapy—which we had prearranged for them.
What did the pair first notice about each other when they met?
“His eyes — they were a gorgeous blue color,” Eliza said.
“Er, her teeth,” Mark revealed. Her teeth? “Well, she had a really great smile.”
So far, so good. They were attracted to each other.
At Souvla, they shared fries, a chicken salad, and a bottle of red wine and chatted about dating and what they did for a living. “The food was great,” Mark said.
Because they were about to attend their first couple’s-therapy session together, on their first date, the pair decided to imbibe before the potentially nerve-wracking experience. They were glad to break the ice and get to know each other before getting to their issues with a near stranger.
“The goal of a first date,” said Jeremi McManus, the psychotherapist and dating and relationship coach they were meeting later in the evening, “should be to just determine if they’re interested in going on a second date. That’s it.”
When it was time to go to their couple’s-therapy session, the pair decided that they could do with another glass of wine. After leaving Souvla, they headed to a nearby liquor store and picked out cheap canned wine, with plans to drink it during the session.
But when they showed up stumbling and laughing, Jeremi, their therapist, wasn’t exactly thrilled.
“They seemed pretty inebriated when they arrived, so I wasn’t OK with them continuing to drink.” Since drinking during a session raises ethical issues for a therapist, he requested that they wait until after they left their session to continue with boozing; the couple reluctantly agreed.
So what’s it like having a couple’s-therapy session on a first date? The idea of going to therapy is something that even those who are in serious relationships may reject or be opposed to. For Mark and Eliza, the details of the session were a little hazy due to their wine consumption pre-session. Luckily, there was an objective (sober) third party we could rely on—Jeremi. (Prior to the session, TBI had coordinated with Mark and Eliza to authorize Jeremi to release the details of the session to us.)
Jeremi started the session with the reason why couples generally come to see him: differences over issues that often revolve around children, sex, or chores. He began the session with an open question: “Is there anything you want to talk about?”
“Just please don’t make me cry,” Eliza said.
“It’s kind of weird, but I’m game to talk about anything,” Mark responded.
Mark was in favor of talking about everything. He goes to therapy on his own and was comfortable discussing his feelings. Eliza was more apprehensive and guarded.
According to Jeremi, the elements needed for a successful relationship and compatibility boil down to geography (where both individuals want to live), a shared desire to have kids or not to have kids, compatible attachment styles, and attraction/chemistry.
Jeremi got right down to business: “How do you feel about having kids?” he asked.
Eliza said that she didn’t want kids, but Mark said that he did want kids. After they shared their opposing views, Jeremi noted that there was an energy shift in the room — they didn’t want the same things. We needed to get the scoop. In his professional experience, is it a good idea to talk about these serious topics on a first date?
He recommended that you have harder conversations (about kids, geography, and attachment styles) on date 4 or 5 but that there’s no need to have them on the first date. He also introduced us to the 30/90 rule. Basically, you don’t want to make a person your official partner—or define the relationship—before the 30-day mark; you don’t know each other that well yet. At the same time, it’s best to have these hard conversations before the 90-day mark, especially before you become exclusive.
The session finished after an hour. Relieved, Eliza and Mark shared a mutual exhale of “Well, that was pretty strange” the moment they stepped out of Jeremi’s office, opening their canned liquor-store wine and chugging it outside on the street.
They headed to a bar to have a few more drinks and to process their therapy session, agreeing that attending a couple’s-therapy session as a first date was hilarious. On their way to the bar, they ran right into one of Mark’s co-workers and her boyfriend, but Mark decided not to tell her what they had been up to. It just would have been too hard to explain.
So did they kiss?
“Yeah, we did. Well, actually, we…ah, I just want to leave it at that.” Mark said, leaving us hanging off a cliff of curiosity.
“I think we did?” Eliza said.
Did the two fall in love after sharing their personal feelings about love and life with Jeremi? Were they now optimistic about the dating scene in San Francisco after years of failed first dates? “We texted after and decided to just be friends,” Mark told us. “We’re on the same page with it. We think maybe a spark was missing.” (Or was it possible the spark was extinguished by all that wine?)
Would the two hang out as friends? “We could. She’s super-funny, and we have a lot in common,” said Mark, “but I wouldn’t recommend a couple’s-therapy session for a first date next time. However, I do consider the date a success — and now I have a great two truths and a lie.”
What was Eliza’s take on the overall date? “It was fun meeting Mark,” she said. “There wasn’t a real connection, but it was an interesting experience. We had a really fun time, though.”
Eliza’s favorite part of the date was meeting Mark. He was outgoing and fun. Mark’s favorite part of the date was dinner and drinks. And the least favorite part of the date? Their hangovers.
Interested in our editorial team setting you up on your very own blind date for your chance to find love? Submit your application here!
