Ben Orenstein

Hi, I'm Ben!

I spent much of my twenties dating without direction, and a lot of my thirties focused on building my career, so I've not met the love of my life yet. I made this page to help change that.

The basics

I'm 42, 6'4", and date women. I've never been married, but I'd like to change that. No kids yet, but I very much want them.

I'm looking for a committed relationship. I'm open to standard monogamy or (once we've built a strong, loving foundation) something more monogamish.

I'm ethnically Jewish (50% Ashkenazi) and love the culture, but I wasn't raised with any religion and don't practice any now.

My home is in Somerville, MA and I'm pretty planted here. Last year, I bought a lake house with my family. We're there almost every weekend in the summer, and it's made our already-close relationships even stronger.

Ben with Jason

I'm, uh, on the left.

Below you'll find more about my family (they're wonderful), my work (software company co-founder, now doing passion projects), my singing (barbershop quartet, symphony chorus), what I appreciate in a partner, and how to get in touch.

Ben at Fenway

Bottom left (2021)

Family

I won the family lottery. It's almost certainly the best thing about my life.

I have a younger brother who lives nearby and is one of my favorite people. He's married with a young son and daughter. I knew I would enjoy being an uncle, but I'm liking it even more than expected. I almost can't talk about my niece and nephew without smiling. I wrote an essay about an impactful experience with my niece if you'd like to get a sense of the vibe.

My parents also live nearby. My mom is smart and warm, and my dad is ridiculously handy and protective of his people.

They're a very welcoming group. We're all excited to integrate my eventual partner into the crew.

Ben with Addie
Ben with Ethan

These kids are so cute it's criminal to have to blur their faces.

Work

Ben Orenstein

I'm the co-founder of a software company I started in 2018 with two friends. It went really well! This year, my co-founders and I put new leaders in place and stepped away from day-to-day operations.

I'm lucky enough that I don't currently need a day-job, so I spend most of my time pursuing passion projects. Lately, I've been getting rather involved in local politics (I recently hosted a mayoral debate in my city!) and building a community called Fractal Boston. Fractal is a group of friendly, ambitious people who eat dinner together every Sunday and help each other grow.

Singing

One of the things that brings me the most joy in life is singing.

I was fortunate to be raised by musical parents who encouraged me to join choruses at an early age. Thanks to them, I've been singing in some ensemble or another for ~30 years.

Currently, I sing with the Tanglewood Festival Choir, which performs with the Boston Symphony Orchestra.

Before that, I sang in a barbershop quartet for 10 years alongside my brother. I miss that group a lot and hope to start a new quartet someday.

I've had so many rich experiences in those groups, and I'd love to tell you about them in person.

But for now, here's a little glimpse of my quartet at one of our coolest gigs:

My quartet singing the National Anthem at Fenway Park. (2016)

Meditation

I've been an on-and-off meditator for years, but I've been on a bit of a streak lately! This year I went to my first 4-day retreat, then did a 7-day that was incredible. I've signed up for another 7-day next year, and could see doing even longer. I'm partly convinced that getting to know your own mind is one of the most important things you can do.

Things I love in a partner 😍

  • You're emotionally warm and have nurturer energy. You have a ton of love to give, and are excited about receiving it as well (I'm very affectionate and always have been).
  • You think we'd be good at making each other laugh. I seem to value having a funny partner more than most. I've found it makes life so much more enjoyable. I love quick-wittedness and callbacks. These days, I most enjoy the comedy of Shane Gillis, Taylor Tomlinson, Mike Birbiglia, Jordan Jensen, Tom Segura, and Bo Burnham.
  • You're excited to start having kids in the next couple years (after dating, marriage, and at least one serious adventure).
    • You’re excited to start having kids in the next couple years (after dating, marriage, and at least one serious adventure).
    • Becoming a father is very important to me, and I’m open to a few different paths to get there — ideally having biological kids together, but I’d also consider options like surrogacy or adoption if that’s something we both feel good about.
  • You're willing to live near Boston most of the time
    • This is a pretty hard deal-breaker for me. I very much want to live near my family a lot of the time. That said, if there's a part of the world that's important to you to be in, I'm down to live there some of the year! (Want to get away from New England winters, for example? No problem.)

Things I would be excited to do together

(Just some rough ideas. Naturally we're going to come up with our own list.)

  • Choose a time each week to check in and connect, and treat it as sacred.
  • Decide which of life's default settings we're into, and which we think we can improve on.
  • Start a business (Highly optional! Only if it flows).
  • Create the circumstances for spending lots of time with the people we love.
  • Pick a doubles sport and get into it.
  • Telepathically communicate that we're ready to leave the gathering.
  • Improve the societies we're a part of.

Things that might not work for you

  • I am socially quite liberal, but my economic views lean libertarian. I tend to think that capitalism and free markets usually (though not always!) produce better outcomes than their alternatives. I don't automatically think big businesses, corporate profits, or rich people are bad .
  • I'm a bit allergic to people using astrology as a truth-finding tool.

Getting in touch

If you think we might be a match, I'd love to hear from you: ben@benorenstein.com

Please don't feel like you need to include as many details as I have here. However, I'd appreciate it if you included at least some basics and a few photos. If you have links to online presences that I can check out, that'd be great too.

I hope to hear from you soon! :)

Bonus Photos

Ben on boat with Winnie
Ben with SF friends
Ben at the lake