Updated: ‘When You Know, You Know’: Upper West Siders Share Stories of Lasting Love

By Liza Cooper

As a love and dating coach, I speak regularly with singles who are searching for love or are in the early stages of dating.

Every week, I go out into the streets of the Upper West Side, carrying a big red sign, asking strangers for their burning questions about love, dating, and relationships.

Many passersby are more than willing to share their romantic questions and quandaries with me. 

Recently, I met a woman named Katia, chatting with her friend outside a café on West 72nd Street. Her friend didn’t want to talk about love, but Katia did. She posed one of the questions I am most frequently asked by singles in the dating world.

Katia, age 32, single: I recently started dating someone. How do I know if I am with the right person? 

The Love Coach (TLC): One of the most important things to notice is how that person makes you feel. 

Katia: I feel excited when I’m with him. He’s open to feedback and communicates well, so that makes me comfortable to speak up. It feels promising, but can I tell if he is the one after only six or seven dates?

“How did you know?”

After my conversation with Katia, I interviewed a variety of Upper West Side couples about their relationships, and posed a version of Katia’s question. Last Saturday, I spent the afternoon at the West 104th Street Yard Sale asking random couples: “How did you know?”

Corey, 38, and Emma, 36 

Emma: On our first date, we talked until 4 a.m., even though he had a marathon early the next day. 

Corey: How could I leave? I wanted to talk to her all night. 

TLC: That’s beautiful, chemistry from the start. How did you know this was the real deal? 

Corey: In past relationships, I was slow to meet a girlfriend’s family or to use the L word. With her, I broke all those rules, because everything was easy and fun. She had two dogs and that was the icing on the cake. 

Emma: Something traumatic happened to us, too. We lost a pregnancy early in our courtship, and he took care of me, so that I could heal. His support meant everything. 

TLC: When you go through hardship together, how your partner shows up tells you a lot. 

Emma: Before I met him, I struggled to find someone I clicked with. People would tell me, ‘When you know, you know.’ That drove me crazy, because I never experienced it. But I realize the saying is true, because with Corey I just knew. 

Ruth and Joe, 59

Ruth: We grew up a few blocks from one another, went to the same schools from when we were 5 to 18 years old, but we were in different social circles. 

Joe: Admittedly, I had a crush on her from kindergarten on, but didn’t have the courage to act on it.

Ruth: We finally met and spoke at a high school reunion years later. We were 52! We’ve been together ever since. 

TLC: How did you know this guy from kindergarten was for you?

Ruth: That’s a crazy story. We planned our first date, but a tragedy in my family made me cancel. He was there for me, even before our first date. I knew he was special. 

TLC: That speaks volumes. What are the qualities you love about one another now?

Joe: She’s a strong woman, and I was attracted to her since we were kids. We like the same things.

Ruth: But we are opposites (laughs), in everything, including politics!

TLC: Different politics! How do you navigate that?

Ruth: We don’t talk about it! I’m hot-headed and have a terrible temper. He stays calm, and never gets angry. He was kind from the start. 

TLC: Wonderful traits. What’s your tip for singles who want what you found?

Ruth: We were 52 when we fell in love. Never give up on finding someone and go to that reunion!

Simon, 47, and Sarah, 43

Simon: I had just come back from an extravagant adventure in Madagascar and was in peak bachelor mode. As a producer, I was invited to a press conference for Erykah Badu [an American singer-songwriter] at the Montreal Jazz Festival. The only seat available was in the front next to this gorgeous woman. I sat down and said, “Do I know you from somewhere?”

Sarah: I didn’t even look up. He started telling me about Madagascar, which he said was ‘sexy’. That piqued my interest. 

Simon: Then, a lot of people rushed in with Erykah, and Sarah vanished into the crowd. I was crushed.

Sarah: Then I saw him later and my heart dropped, because we had a connection. He was a charming, forward New Yorker, so different from the men in Montreal

TLC: What made this the relationship you both wanted?

Simon: There is a telepathy between us. As someone who has dated extensively, I know that is very rare. She is the sexiest woman alive and has this massive vinyl collection of all the jazz and blues artists that I studied – so she’s like a fantasy character that I dreamed up. 

Sarah: He is this perfect balance between playful child and mature man.

TLC:Two endearing qualities to find in the same human.

Simon: We met because of jazz, and now we are a jazz powerhouse couple.

Sarah: I had vowed to never remarry, but a year and a half after my divorce, I was married to this guy.

Edafe, 34, and Nick, 34

TLC: When did you know this was it?

Nick: We were walking around McCarren Park in Brooklyn and joking around. I realized I could spend the rest of my life with Edafe, because we had fun together. 

Edafe: For me, it was a different moment. I was washing dishes during the pandemic and said to him, “We should get married.” Everyone was breaking up around us, but we became stronger as a couple. During that time, I lost my father. Nick supported me. That’s what love is – having somebody to rely on when you are in need. 

TLC: Joy and caring – you have both. 

Edafe: Society tells us love should be watching sunsets, things like that. But it’s about improving together and being there for one another day after day through the routine, and through challenges. He did those things for me. 

TLC: What did it mean to feel supported by Nick through all of that?

Edafe: If he didn’t leave me during those hard times, he would never leave. I knew he was my person. 

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Editor’s note: The final couple was added shortly after publication, when their picture arrived.

Liza Cooper is a Love & Dating Coach. If you have questions or quandaries for her, please put them in the comments.

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