Love, Dating, and Relationships on the UWS: Singles and Couples Share Their Thoughts and Experiences

By Liza Cooper

As a love and dating coach serving singles across the country, I was surprised to learn that in our own Upper West Side neighborhood, with a population nearing 227,000, about 53 percent of residents, roughly 120,000 people, identify as single, divorced, or widowed, compared to about 47 percent, roughly 107,000 people, who identify as married, according to data provided by the 2022 Census Reporter. 

Who are these singles and couples and how are they doing? I wondered. So, over the past week, I asked Upper West Siders I knew casually, as well as strangers in Riverside Park and in front of Westside Market on 97th and Broadway, about their dating and love lives, and their enduring relationships.

While some passersby quickened their pace when they saw my giant sign that read “Talk to me about…love, dating, relationships” many were eager to speak to a dating coach about their struggles seeking romance, as well as their issues within long-term relationships. They also talked movingly about the joy that comes with good partnerships. 

Here’s a sampling of what I heard from the Upper West Siders I spoke with. Some names have been changed to protect privacy 

Alessandra, Single, Age 34

The dating process until meeting my boyfriend was basically a tragedy. Forget sparks, there wouldn’t even be a click around conversation with the guys I would meet. I never tried dating apps, because that seems like the last frontier and just another job. My partner and I met watching the sunset near the 72nd Street boathouse. It started off as a friendship and we would meet for coffee, a drink, or to play pool in the neighborhood. It was obvious from early on that he was different and special, and I felt comfortable with him right away. 

Alan, Single, Age 55

Dating can be fun, but it can also be a chore. It’s like a conveyor belt – another date, another dinner. I’m looking for someone who gets me, who is curious about their inner and outer worlds, where we laugh, and I look forward to spending time with them. It’s hard to find! Since I work from home, I don’t have a lot of time to randomly meet people, so swiping on dating apps is all I’ve got – the fast food of relationships. If I lived in a small town, there might be only a few options, but in NYC there are so many choices that you think there could be someone else who is better. 

Leora, Married, Age 48

We met at synagogue. He was cute, but his sense of humor was the big draw. Laughter and hard work have gotten us through more than twenty years, including some very challenging times. Both of us came into marriage skeptical – my parents divorced early, and my husband’s parents had a great deal of discord. Conflict is part of relationships, but we work hard to repair when we fight, by owning our bad behavior and honoring the other person’s soft spots and traumatic experiences of marital conflict. We’ve come so far in our time together.

Ella, Single, Age 45

It’s likely one day that I will want to date again, but after a complicated divorce and now raising an 8-year-old, romance is not something I think much about.  Right now, I am in control of how things go and I don’t need to check in with another person about any decisions. Also, I’ve discovered that I hated breaking up with people – because I didn’t want to hurt them – so I stayed in unhappy relationships for a very long time, instead. Fortunately, I have a group of single friends who happen to all be amazing. That is not the worst club to be a member of. 

Marck and Diana, Age 18

Diana: This is our second time hanging out. We talk and text a lot though. Today we spent the day in Central Park in a cute little spot eating frozen yogurt and just talking, because we have so much in common, like watching the show Dexter. I like him [Marck] a lot.

Marck: I slid into her DMs on Instagram because she was going to the gym and so was I. It sparked a conversation. We have those little things that connect us that others might think are insignificant. I like her a lot too, but we are just enjoying each other’s company, and seeing where things go naturally. 

Andy, Married, Age 42

Eleven years ago, I met a man on match.com. He visited my West 87th Street apartment early on and never left. To be honest, I knew within minutes of meeting him that I wanted to marry him; I proposed under the Eiffel Tower. Lee was the opposite of everyone I had met before, and in some ways the opposite of me. I have big feelings; he is grounded. I can be grumpy; he is always cheerful. We both have loving families, though. Although we left the Upper West Side recently, we miss it dearly, and can’t wait to go to Metro Theater when it reopens. Today we are best friends and partners with a lot of gray hair. 

Maddie, Widowed, Age 89

I had two wonderful marriages. After the passing of my first husband, a friend pointed a man out to me at church and said, “That will be your second husband.” He was, and absolutely adored me and my children. I have fifteen grandchildren, and I tell them that the best relationships are when each partner believes they are the one giving 70 percent. When my husband would say something insensitive, I would respond, “I think you meant to say…” He would tell me that I was editing him, and then we would burst out laughing! My best advice for relationships is to always spoil someone you love, because it’s wonderful to be spoiled. No more romance for me though…I’m 89! 

Kara, Single, Age 58

I always thought that if I put my mind to something, worked hard at it, had a positive attitude, that I would see the outcomes I hoped for. But I have done all of that in dating and still haven’t met someone. I have tried every dating app, sat with my laptop in cafes, met with matchmakers. But the thing that boggles my mind the most is that I have many extraordinary friends who care deeply about me, and none of them know anyone great and available to introduce me to. How is that possible? I’m financially independent, warm, open; I have stopped trying to find love, but I’ll never give up hope. 

Barbara, Married, Age, 57

At a singles square dancing event on West 100th Street, I met a man who told me, “The Having Kids Ship has passed me by.”  Since I was in the process of adopting a little girl from Russia, I knew I was going to pass this guy by, too. But then he asked for my number. For me, he had a lot of red flags – in his 50s and never married, no interest in kids, and lived for 30 years in a studio apartment a block from his parents. But throughout and since the adoption of my daughter, I saw that he was meant to be a father. Things are not always easy, but I was accustomed to partners who didn’t prioritize me. He’s the opposite, and he is also very funny. Where I once saw all red flags, now I see all green. 

Udochi and Natalie, Single, Ages 23

Udochi: Last summer, I had a brief romance, and it was the best time of my life. I have never experienced that before. He was quiet, gentlemanly, put me first, and let me shine. I felt seen and loved, but he had to go back to his country and I sabotaged it saying it will never work. We stayed in touch over the past year, though. He’s coming back soon for a few months, and I’m hoping we can continue where we left off.

Natalie: I am disgustingly single and haven’t dated since high school. There hasn’t been anyone I’ve wanted to go out with, and I always download and then delete all the dating apps. It’s hard for me to make space for someone, because I like being alone and I’m used to it. I’m shy, and Udochi is an extrovert, so we make great best friends. 

Liza Cooper is a Love & Dating Coach. Her winning Moth story about finding love after divorce went viral on social media earlier this year, while an article about her amicable marital split was featured in The New York Times in April. 

If you have questions for Liza or thoughts to share, put them in the comments. 

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