I
’ve had a crush on a coworker exactly once. We were both in high school, and we both worked at the rec center. Nothing ever came of it (thank god), but after college, as my friends and I all began our careers, the idea of intertwining work and dating became more than a teenage fantasy as acquaintances confessed their desire to meet romantic partners in the office and more than a few already-established couples decided to work together.
Navigating the politics of working alongside a significant other has always appeared complicated to me from afar, so I was curious to hear from people who actually do it successfully. To better understand the struggles, rewards and surprises inherent in relationships that either started at the office or ended up there, I spoke with three couples who work together in different capacities. Keep scrolling for a heavy dose of relationship wisdom, replete with all the highs and lows you might expect.
Lupita and Stanley
Lupita and Stanley work together in Philadelphia at 12th Street Catering, where they first met over 20 years ago when it was just a small café.
What led you both to your jobs at the café where you met?
Stanley: I came to America from Jamaica in the fall of ’86 after my mom passed away suddenly. I come from a family of working-class, hard-working people. My main goal was to play by the rules, work hard and see where that went. I started at Cantina [the café that has since become 12th St. Catering] in the spring of ’87, when it was a very small company. Eighteen years ago I became the executive chef.
Lupita: I’m from Mexico. The economy was really hard there, and I had to help my mother because my father passed away when I was 15. I worked for a Mexican family that was moving to Philadelphia, so I came here with them. After they moved away, I stayed and found a job at Cantina. I started by doing dishes — I didn’t even speak English. I tried to learn the language by listening to the customers. Slowly I started to speak with customers and learn the cooking. I’m the general manager now.
Did you two have an instant connection when you first began to work together?
Lupita: When we met, Stanley was married, and I was dating. We communicated with one another through a Spanish-English dictionary that I kept with me, translating everything. I helped him prep in the kitchen. Once we started to understand each other, we became best friends. I got married after that, and he got divorced. My marriage lasted about six years, and he encouraged me to get marriage counseling toward the end and helped me find places. He was supportive. About four years after I got divorced, Stanley and I got married. This year is our 10-year marriage anniversary.
Is it difficult to balance your work and personal lives together?
Stanley: Lupita is my best friend, but we always kept work separate from dating. Even today, she’s the GM and I’m the executive chef — it’s like east and west. We’re very passionate about what we do. Therefore, we don’t let our personal lives be a part of our work environment. When we’re at home, I don’t really talk about work much. When I leave work, I leave the job right there.
Lupita: In my position though, I get a lot of phone calls and emails, and I have to travel with them. That’s the way it is in my job, and that helps make our company successful — that I’m there to answer any concerns and problems. It’s hard, but we balance it. We never get upset with each other.
What are your favorite ways to spend time together outside of work?
Stanley: Church, movies and we like to travel when we have the chance. I love to go to Jamaica, and we like to go to Mexico. But we have a daughter in college now, so it’s hard to travel.
What are some of the most fun or memorable times you’ve shared working together?
Lupita: It’s fun when we cater together for famous people. We’ve done events with people like Will Smith, Warren Buffett, and Eva Longoria.
Stanley: Everyone dressed so nicely to see Mr. Buffett, and he showed up dressed in a simple blazer with no tie. We were mingling with one of the world’s largest investors! One of the best memories was on a recent catering job for a nice private party. The truck arrived, and when we opened the door to unload the food, it was completely empty. The truck hadn’t been loaded with the food. We had to rush back. We just laughed — it was a lot of fun.
What’s the biggest lesson you’ve learned from working together?
Stanley: We’ve learned over the years to stay humble. Stay sharp, stay creative, keep your feet on the ground — those are the qualities that were taught to us, and it’s what we maintain as we travel through life’s journey together. Also, you have to try your best to understand each other…
Lupita: And support each other.
Meghan and Michael
Meghan and Michael are the co-founders of Curiosity Lab, a purpose-driven marketing company that helps organizations build community around their brand and values.
How did you meet, and how long have you been together?
Michael: I was in an eight-year relationship throughout my twenties. After that, I started online dating, and I met Meghan on the app Happn. We texted on a Tuesday night, all night, and then she ghosted me for two days, but our conversation had been so deep that I just laid it out there and said, “Look, I thought we had a really connecting conversation, and I have no intention but to be a gentleman. Do you want to give this a try?” She responded right away.
Meghan: You don’t get many people who get that real and vulnerable on a dating app — you usually just get a lot of small talk. Before we met, I gave him homework — I sent him this really long article called “Intentional Dating” that has inspired my dating philosophy. He read it. We had amazing chemistry, and we acknowledged that pretty quickly. We’ve been together two and a half years now.
How did the idea for Curiosity Lab come about?
Meghan: I had co-created a company called Canvus, which I still have as a side project. With Canvus, we host small-group travel experiences where we explore different cities around the world through the lens of feminism. Michael and I started workshopping around that idea. Only a month and a half after we met, he came with me on a retreat in Maine to help brainstorm. This was right around the 2016 presidential election, and we both woke up the day after it and realized that we wanted to get serious about the purpose-driven work we’d been exploring and turn it into a full-time endeavor for both of us.
Michael: We moved really quickly. We started dating in July, started collaborating on projects together around August or September, moved in together in October, and then the election happened in November, when we got serious about it. The main goal was to help organizations build community around their values.
Were there any moments of hesitation about starting a company together so soon?
Michael: I had a history of building a business with one of my best friends, and it didn’t go so great. I knew how difficult it could be mixing work and a close personal relationship. So at one point we paused on the brainstorms and figured out what it would actually look like for us to work together.
Meghan: Sometimes other people would say, “Be careful what you’re getting into,” but I don’t think we ever had a ton of hesitation. It’s so incredible to be with someone romantically with whom I can also create.
What’s been the most surprising aspect of working together while living together?
Michael: Because we’re spending every facet of our lives together, from personal to professional, there are things that another couple might uncover throughout a 10-year relationship — like differences in upbringing and communication style — that we uncover every couple of months. We’ve had to figure it out, and the stakes are higher since we’re start-up entrepreneurs together. Neither of us comes from a trust fund that gives us a safety net; we’re just making it happen between our savings and what we earn, and that brings in a level of stress at times.
Meghan: We didn’t have an office right away, so we were doing everything from our apartment at first, and that was a lot. It was difficult not to have any separation from when we were working and when we weren’t. Because we’re together all the time, we brainstorm all the time — we have a whiteboard in our living room.
I’ve been surprised by how much I’ve learned about myself during this time, like that I have a hard time receiving feedback from people I’m really close with. That’s only come out in this professional setting. In traditional professional settings, sometimes people won’t push you to your max because of politeness or a lack of care. To be with someone who is so close with you that they’re like, “You could have stepped it up,” without a sugarcoat, is really effective in making you a better version of yourself.
What’s been the most rewarding part of working together?
Michael: When we first met, I was working at a major advertising agency. I was getting paid really well, but I hated getting up on Monday mornings. I was so inspired by Meghan’s courage to leave her job and pursue what she loved. It made me ask myself more philosophical questions about what I was doing with my time. Now I feel this intense passion for my work on a daily basis, and Meghan gave me that confidence and support to do things I never thought I’d be capable of doing or worthy of doing.
Meghan: An experience we had this past summer was also extremely rewarding for us. We had a team of interns, and we wanted to do with them what we do with our clients — figure out our shared values and what we want to create in the world. We had no idea what the outcome would be. Together, we decided our goal was to fight divisiveness in our country and get people to come together and have conversations about what we have in common. We created a campaign called “Actually Curious” and made a card game inspired by the New York Times article “36 Questions That Lead to Love,” featuring conversation-starting questions that progressively get deeper and more vulnerable. On the interns’ last day, we also created stencil art — and I guess this is illegal — but we went rogue in the middle of the night and pasted giant posters around New York that ask people thought-provoking questions. That process of actually creating something physical together was so incredible.
Sara and Amber
Sara and Amber are an entrepreneurial Brooklyn-based couple who work together on Sara’s company, Harvest & Revel, an alternative catering service focused on health and sustainability.
How did you meet, and how long have you been together?
Sara: We’ve been together about six and a half years. We met for the first time standing in line outside of a rooftop bar in Brooklyn. I was really bold back then.
Amber: She introduced herself and said, “Hi, you’re beautiful. I’m Sara.” We hung out for a little bit, but then we didn’t see each other for another year. We were both dating other people at the time. When we crossed paths again, we exchanged information. Sara asked me out for tea, and that’s how it all started.
What was it like working together to create Harvest & Revel?
Sara: Prior to founding Harvest & Revel, I was working in private wealth management at an investment bank. In my free time, I started cooking and exploring the use of seasonal and organic ingredients. I began to host pop-up events, and Amber was crucial in making them happen. She was supportive in pushing me to explore and helping me develop menus, recipe test and prep. She was also learning about cocktail making at the time, so she did the beverage program for the pop-ups. It turned into this seasonal event we were producing together. Even though it became my company, she always jokes around, saying, “I’m the owner,” because she’s been doing it from the beginning. Even now that I have a team of chefs, Amber still captains a lot of the events and does operations for the company, like onboarding staff.
Amber: The general idea was never for it to be our company. The vision Sara had was something she wanted to explore, and I just wanted to be as supportive as possible, asking, “What do you need to make this vision come true?” We had to have talks about what it would look like when she quit her full-time job, because the events started to become like another full-time job when we got home from work and on weekends. It was a lot.
What’s the biggest challenge of working with your partner?
Amber: In the beginning, it was difficult because we were in the early stages of our relationship, so we were still learning the ways that we both communicate, learn, process and handle stress.
Sara: At first, during stressful times — and producing an event is pretty much stressful 100 percent of the time — it was hard. There was a point when Amber was like, “So, I think you’re going to need to get a business partner because this is not working for me.” I’d get super snappy with people who are slow processors because I’m a very fast processor, and that’s something we know now. We’ve talked about it, and now I’ll slow things down or repeat things, and Amber will be patient with me sometimes not being patient.
What has been the most surprising part of working together?
Sara: It was a nice surprise to see how reliable Amber is in every circumstance. Even now, if I need to leave an event early or can’t make an event and Amber is captaining it, I know that everything is going to go smoothly. I’ve felt like this with her since the beginning, and that’s really rare to come by — someone who can pretty much succeed with any role. I don’t know if it’s surprising now that I know Amber’s character, but it was a huge gift to find a partner who, if I literally had to leave the company, would handle everything perfectly.
What are the most fun or rewarding moments?
Amber: When we’ve taken on a super large event where we need all hands on deck and then we pull it off and receive great feedback, even if it may have felt super hectic on our end. It’s so great to just get in the car to go home and debrief and celebrate. It sets another bar to show that we can do this.
How do you spend time together to get out of work mode?
Sara: We’re really big on leisure and celebration, so we make up lots of little holidays and date nights. We’re always celebrating something — we’ll be like, “Oh, it’s Wednesday! Do you want to celebrate?” Or we’ll be at a restaurant, like: “Today’s our anniversary…of 6 years and 33 days!”
What’s the best piece of advice you’d give to a couple about working together?
Amber: A desire to work together doesn’t mean that you should work together. It’s important to interview each other the same way you would any other potential business partner. You need to see what you could each bring to the business partnership, the same way that you should be thinking about what you can each bring to your relationship partnership.
Illustrations by Ana Leovy.
