Food Influencer's Past Dates Reunite

TL;DR

Jeremy's Date Reunion: TV producer Jeremy Jacobowitz reunited with five past dating-app matches in New York, with five others joining remotely.
50 Dates Over Decade: He has met around 50 women from apps in ten years, mostly for one drink at regular bars, with interactions usually fizzling after one date.
Mixed But Positive Feedback: Women described him as nice but self-absorbed, lacking curiosity, yet ranked him as a positive date compared to others.

The story at a glance

Jeremy Jacobowitz, a 35-year-old food influencer and former TV producer, gathered ten women from his past dating-app matches for a group photo shoot and chat in New York. Five met him in person, while five shared recollections remotely. The piece explores their memories of unmemorable, low-stakes dates and reveals patterns like his self-focus. This is reported as a quirky experiment into app-dating reflections.

Key points

Jacobowitz prefers low-commitment drinks at familiar bars to manage social anxiety from past struggles with weight and talking to women.
Most dates ended after one outing; his longest app relationship lasted 3 months.
Women often forgot details, like Taylor K. needing to check his profile; some noted his height, sweating, or Bobby Flay fandom.
Complaints centered on him not asking questions (e.g., Morgan: no questions in three hours) or focusing on his career (e.g., Julia's Instagram incident).
Reunion felt like networking for women; Jacobowitz was anxious, forgetting most dates, but called it fun for him.
His Hinge prompts highlight Simpsons fandom, sushi preferences, and disdain for rainbow bagels; he uses Hinge, Bumble, Raya, Lox Club.
One match (Arielle) never met; another (Caitlyn) flaked due to a conflict.

Details and context

Jacobowitz, who runs the Instagram account Brunch Boys, started app dating ten years ago after personal insecurities. He estimates 50 matches met in person, sticking to quick drinks to exit bad ones easily. Women ranged from 23 to 35, with dates from 2014 to 2022; some led to brief repeats or professional ties, like Julie collaborating on food projects.

At the reunion photo shoot, awkward silences marked the vibe: Morgan noted his blank look upon seeing her, and Taylor K. saw it as a "networking event." Jacobowitz defended his interviewing style as natural, avoiding forced questions. Overall, women viewed him positively against New York dating norms, despite nitpicks.

Key quotes

“The thing I remember the most is that over the course of three hours, he did not ask me a single question,” said Morgan.
“I don’t want these dates to feel like we’re just quizzing each other,” Jacobowitz said.

Why it matters

This experiment uncovers patterns in modern app dating, like forgettable first dates and mismatched expectations on conversation. For daters, it highlights the value of curiosity and low-stakes meets, while showing how exes might network post-fizzle. Watch if Jacobowitz's approach evolves or leads to more matches, though outcomes remain uncertain.

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