A 52-Year-Old Guy Dishes on Dating in New York City

Posted by in dating after divorce, dating in midlife | 0 comments

The one thing that threw this divorced single dad for a loop? Dating in New York City in his fifties. Turns out it can be both challenging and fun. 

My radio guest, Matt Sweetwood, is the U.S. CEO and President of beBee, Inc. He is well known for his innovative and transformative ideas in marketing, social media, and business development. He was President of Unique Photo, NJ’s premiere camera store, for over 28 years. However, by far, his greatest achievement is having raised five successful children to adulthood as a single dad. He’s the creator of the Man-Up Project, helping other men though fatherhood and life. He is a regular contributor on national TV and to several publications in the social media, photography, business, ethics, politics and parenting arenas.

52-year-old Matt recently moved to Manhattan after living his entire life in New Jersey. We had a lively discussion about his experience with dating in New York City in midlife. Read highlights below of episode #258: A Manhattan Middle Aged Man’s View of Dating. 

A 52-Year-Old Guy Dishes on Dating in New York City

Can you share what it was like to raise your five kids alone?

When I was younger, success in life was measured by being married and having a picket fence and a dog. If you told me I’d have raised five kids on my own and gone through two divorces, I’d have said, “What, how did that happen?” 

The truth is, it’s the best thing that ever happened to me. I married young and married the wrong person. When you make the wrong choices, you don’t recognizes the red flags. In my case, they were red blankets that spread over my king size bed! 

We had five kids quickly. The marriage deteriorated, and she left us when I was 31 years old. The kids were 18 months through eight years old. I was bankrupt. I had no idea how to be a parent alone and put food on the table. My confidence level was shot. I didn’t know how to take care of the kids. I never aspired to take care of them alone. 

The transformations I had along the way as I went from a boy to a man were: let go of my anger, stop feeling sorry for myself, and raise successful adult kids who are close to me. I wouldn’t be where I am today if it didn’t happen.

I love to help people have a big life and change their thinking. I have immense gratitude for all that I have.

As a person who helps others, do you find it difficult to ask for help or receive help?

I don’t think I ever had anyone in my life who provided me with help. But if you don’t ask for help, it won’t come. The Torah says you should seek out a friend in life who can help you. I’m always in the position to give help. If I wake up and feel down, I go help someone who’s feeling down. [Listen to the interview, as this conversation was quite rich and a bit confrontational].

What is dating in New York City like?

I lived in New Jersey for many years, and I sold my business and moved to New York City. Northern New Jersey is mostly suburban. NYC is a place with tons of singles. The crowd is mostly 20s and 30s. It’s more difficult to interact with older singles. And finding quality dates is just as difficult here as anywhere else.

I have a lot of options, but not for a sustained relationship. What I find bothersome about dating today is that internet dating gives people an excuse to not treat people nicely. People just stop talking to each other. They realize there’s another swipe behind you, so goodbye. There’s always something better coming along. New Yorkers are a bit tougher, too.

One thing I see frequently, is when dating a woman in her late 30s or early 40s, they bring up children on a first date. Many have not yet had kids. It’s interesting to bring up kids upfront in an initial interaction. That’s a good way to get a man to run! People have lists. [Listen to what Matt and I say about dating Trump supporters.]

What message would you like to share with women out there to help them find love?

I’m looking for a kind, compassionate, caring, loving woman, and not a prosecuting attorney who’s going to interrogate me on a date. Many profiles talk about what women are looking for. I think women need to talk about what they have to offer. I’m a successful person, and I have options. I like to say, “I can offer _______ in a relationship.” A woman needs to do the same if she wants a relationship.

NYC is also a difficult place to date because it’s easy to entertain yourself and have a great life. Women don’t NEED to be in a relationship. It’s easy to not do what it takes to be in a relationship. Even when you go to date someone, these women are fitting you into their social schedule. 

When you go out with a middle aged woman who still acts like the prom queen from high school who has to do nothing when she’s dating or in a relationship? I am in a relationship when it adds something to my life. 

Unfortunately, our interview got cut off before I had a chance to wrap, but there’s so much good stuff here, you’re going to want to listen to the whole show!

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