Sydney helps mom Jennifer navigate the dating apps. Widower Herb offers daughter Jen tips for a successful long-term relationship, even as bad timing keeps him apart from his longtime love. Both stories prove that the ties that bind us need not be restrictive. They can provide just the right amount of support, at just the right time.

What’s a Quaker wedding? Excerpt from Jen and Chris’s wedding site:

LAURA STASSI 00:07

The parent child relationship. Sometimes it’s complicated, even as parents and children grow older, and especially if new romantic partners enter the picture. But those ties that bind us need not feel restrictive. They can provide just the right amount of support at just the right time. Love is a family affair. That’s coming up next, on dating wall Gray, the grownups guide to love sex and relationships. I’m Laura Stassi.

00:41

Dating apps are so ubiquitous. It’s hard to remember that once upon a time, not too long ago, couples met in other ways.

SYDNEY

I’m just old enough we met Olds we met in a nightclub

LAURA STASSI

that Sydney she’s in her mid-40s. And she lives in Atlanta with her husband and two daughters. Up until recently, Sydney had no experience with online dating. But then Mom Jennifer moved to town. Jennifer’s in her early 70s.

JENNIFER

I actually raised my son and Tampa, Florida. And then once he graduated and went to college, I relocated back to Los Angeles, where I ended up dating and marrying one of my old high school friends and didn’t quite work out as anticipated. So I ended up moving back to Atlanta with my daughter. Since then, you know, my son has relocated to Los Angeles where he is married and has two beautiful boys. And so I fly back now back and forth between Atlanta and Los Angeles.

LAURA STASSI 01:56

I actually had an episode, we called it boomerang love. And it’s very common for older people to reconnect with someone from their home, I believe it.

JENNIFER

And how did that work out for them?

SYDNEY

02:10

That was my question in my head. I was like …

LAURA STASSI 02:16

Can you tell me Jennifer, what, from your perspective,

JENNIFER

02:20

I’m sure there are those out there where it’s just been a blessing. I can’t really use my experience as anything to tie any kind of outcome to, so …

SYDNEY

And that is my mom and in essence, a hopeless romantic.

JENNIFER

02:41

I guess for some people, it is easy to go back and pick up from where you left off because of the initial knowing each other so well. You know, it’s easy. And you think that that’s the way it’s going to be and especially at the age that we ended up getting married. How difficult can it be? We have no children. Yeah, I mean, it’s got to be smooth sailing. Well, for me, it just wasn’t the case. And I was actually with him for 13 years Wait — actually it was 11 years. I’m sorry, 11 years.

LAURA STASSI Oh, that’s a good go.

SYDNEY

That’s what I said, I was like, you gave it a try.

JENNIFER
I felt like when I moved here, I had some work I needed to do on myself. So I had to go back and learn to love who I was, again. And so I did that for about now two, two and a half years. And so that was my journey. And I felt like I just wasn’t ready to look at even getting involved in a new relationship at that point.

03:53

So then, when I decided that that’s something that I might — well actually, I had met, I guess, a couple of guys just on a day-to-day basis. You know, walking in the park or as my daughter loves to say, at Costco.

LAURA STASSI

Go, Costco!

SYDNEY

All true, all true.

JENNIFER

And they ended up being you know, good relationships, but wasn’t really what I was looking for. So I thought, well, what’s the next step? Let’s try dating online. And my daughter decided to help out with that.

SYDNEY

SYDNEY

I see her every day. Like, I stop by either I’m on my way to work, my way home from work. So I see my mother at least five out of the seven days of the week. We are incredibly close. We probably talk at least three times a day. And so I was aware of her wanting to start this journey towards companionship, not necessarily remarriage, but this idea of like having someone to travel with, having someone to have dinners with and spend time with, and I was like, I have friends who have kind of started this online dating journey. Folks that I started working with that went from work colleagues to friends that I spend time with and have around my family, and who I know are pretty heavy into the online dating. And I was like, listen, I’ve got two folks that can help steer our ship. It can’t be me because I’ve never done it. But I certainly know how to recruit the right help to launch just appropriately.

LAURA STASSI

I like that. Your manager, your online manager. Okay, so and when you say you were prompted to do this, Jennifer, you had never been online before? Was it really “The Golden Bachelor” that persuaded you to do this?

JENNIFER
I’m not sure it was “The Golden Bachelor” that persuaded me to do it. But I did in watching it think, well, I mean, if it can work for them, then surely there should be some way. And also, I had a couple of girlfriends who had actually already started. And so they would talk to me about some of their, you know, connections and stuff. And so I thought, well, if they can give it a try, I can as well, although their connections have been pretty short term. So nothing that has really blossomed into like a long-term relationship.

LAURA STASSI

Okay, so tell me how this sort of transpired that Sydney, you’re now helping your mom figure out the apps?

SYDNEY

Well, she mentioned that she wanted to get on the app. And I was like, listen, I’ve got two crusaders that I can have come over and help us set up a dating profile. And so that’s exactly what happened. I called my two girlfriends. And I was like, listen, my mom wants to set up a dating app. Come help us figure out what pictures, what to say, what questions he answer. And these two friends are absolute dears and jumped at the chance as you know, as soon as I threw it out there. And that’s kind of how it came about.

LAURA STASSI

Now, are they around your age? Or are they younger?

SYDNEY

Oh, they’re younger. They’re actually both turning 30 this year.

LAURA STASSI

Oh, so much younger.

SYDNEY

Yeah. Yeah, but they had the experience.

LAURA STASSI

Oh, I love this.

SYDNEY

Yeah, this was like a really a team effort. Generational.

LAURA STASSI 07:16

So can you take me back a little bit to that first time y’all got together?

SYDNEY

Well, there was liquor involved. I was like, we have fun. You’re gonna have to liquor us up a little bit.

That’s what she did. Mom laid out quite a nice charcuterie spread with the wine flowing. So we tried to make it fun, right? Because it’s, it’s supposed to be kind of fun. I mean, it’s serious. But then it’s also, it’s life. And it’s the totality of the experiences. So let’s make it fun.

JENNIFER

It was actually really fun. Just listening to the younger to talk about their experiences as well. It was, it’s interesting, oh, well, I guess we all go through that have the same problems. And every generation, you know?

LAURA STASSI  07:59

Well, that’s what I was going to ask, did they find anything — I don’t know, odd or unusual about your dating pool? The older … okay, let me back up a little bit. What was your dating pool?

JENNIFER

Well, initially, I hadn’t put a deal breaker on age.

 SYDNEY

I did. I put a deal breaker on age. I did put a hard deal breaker on age. I was like, we’re not gonna date anyone that would fall into my dating pool.

JENNIFER

08:29

So we had to go back and change that.

LAURA STASSI 08:34

Okay, in all seriousness, would you have wanted to date somebody who’s younger than your daughter?

 JENNIFER

Absolutely not. Absolutely. I have — have I dated younger than me? Yes. Yes. As a matter of fact, the two other individuals that I had mentioned, they were both younger.

LAURA STASSI

All right, so you put a parameter on the age. Can you give me an idea of what that was?

JENNIFER

I think we decided, like 58 to 75. Or maybe 77. I already had photos. They went through and took a look at the photos and figured out which ones would probably be the best. So I left that decision up to them. But I picked out probably about 15 or 20 photos that they could have selected from.

SYDNEY

And I think when we were looking at the photos, trying to figure out which ones to use, it was important that they were current, right? That they look like mom and so there’s no shock and awe or mystery. Nothing posted from like, 1986. No, all the photos were within the last six months. This is what she looks like. These are the things that she enjoys doing so that they can really tell a true story of who she is.

LAURA STASSI  09:56

Yeah, I’m kind of laughing because my son a few years ago for my Mother’s Day present, he and his then fiancé created a Bumble profile for me. And he just grabbed photos off my Facebook page. And I’m like sweetheart, these pictures, some of them are like five or six years old. And he’s like, well, you still look like that. I thought, oh, he’s my son, he doesn’t understand.

SYDNEY

That’s love. You are ageless in our eyes.

LAURA STASSI  10:26

Yeah, but Sydney, was it hard or a kind of a weird switch seeing your mom, considering your mom and how you know your mom as a person, on a dating site?

SYDNEY

It was a little wild. I’m not gonna lie. Like, you know, the mom that I know has always been married or partnered. And so this idea that she was going to be on an app and quite literally combing through profiles of men. I’m like, what is happening? But then, you know, there’s also part of me too that’s like, if she wants companionship, then let’s not sit back and wait till it finds you. Right? Like, let’s be proactive.

LAURA STASSI

Oh, so easy for you to say.

SYDNEY

11:06

For someone that’s been married for almost 15 years? Yeah.

LAURA STASSI  11:11

Okay, so you had your friends over. You’re having a fun little party. You’ve got the pictures, you’ve  got the profile. And then did you sort of just turn it over to Jennifer or Jennifer, did you need some handholding like, with the winnowing process?

JENNIFER

Well, it’s interesting, because I guess, the first night, I didn’t check. The next morning when I got up and checked, I had a couple of likes. So I ended up texting my daughter going, what do you do with the likes? And you know, how are you supposed to handle that? So that we created a little text chat group, we called it the Hinge group chat. It included the two younger girls as well as my daughter, myself, so that we go into that and go, what do you do when you get a like, and you know, so we, anytime I had a question or whatever, I could go into the text and, and get that figured out.

SYDNEY

And we created a group chat  — it’s like the idea that everything needs a little bit of support, right, that things grow with nurturing, tending. And so we created a little bit of support and community that we could utilize, like, what how do I respond to this message? What do I say? This and that so that it could offer, you know, mom some support on the journey.

LAURA STASSI

I love everything about this. And I think your friends might have a career.

SYDNEY

A little side gig, right? A little hustle? Yeah, for sure. Right.

LAURA STASSI 12:32

Or maybe it will motivate the, you know, in my audience, we’ve got, you know, people who have children who have younger friends who could maybe help us all out here, because I remember the first time I went online, it was like, this is awful. It’s like being at a singles bar. But it’s not your neighborhood. And you know, you don’t know anybody.

JENNIFER

So it’s still scary. Even after you make the connections, it’s then getting to know them and doing your dates and doing all of that. So, but it’s getting out of your comfort zone, which is what I think a lot of people are willing to do now. You know, in order to find love you’ve got to take those steps. You can’t just sit back and think it’s just going to come to you. It won’t happen.

LAURA STASSI

How is it working out?

JENNIFER

There are two currently that I’m seeing. So we’ll see how that goes.

LAURA STASSI

So you’ve progressed from the talking on the app to meeting them in real life?

JENNIFER

Yes. One, I’ve had a couple of dates with, set a third date up. And the other I just recently met, and we got offline as well, but mainly through texting and talking on the phone and planning to meet with him.

LAURA STASSI 13:58

Oh, wow. You know, it’s interesting, because I personally need to get comfortable with the fact we’re supposed to be dating more than one person at a time, you know, until we become committed. And so I know I have made the mistake in the past, and I think a lot of my listeners have, you meet one person and you put all your eggs in that person basket. And then, but you shouldn’t.

SYDNEY

You should have all the eggs in all the baskets until you have a discussion of monogamy. Correct? Right?

LAURA STASSI 14:33

So at what point, Sydney, are you going to want to say, Mom, I want to meet him — or I want to meet him.

JENNIFER

Interesting question.

SYDNEY

I know historically, I’ve always let her kind of drive the train. So I think I’m gonna let that happen this time too. My biggest thing is that, you know, that she’s safe, obviously, and that she feels supported. But I think she gets to a place where she realizes this person makes her happy and that the things they do are an added value to her life well, then yeah, I’m gonna want to meet them.

LAURA STASSI 15:11

And Jennifer, when would you feel comfortable introducing Sydney to someone?

JENNIFER

I think whenever the individual feels comfortable, I mean, I wouldn’t want to put somebody in the position of introducing them to my family if in fact, they weren’t comfortable with that at that point.

LAURA STASSI

Are you interested – okay, I’m going to just ask all the questions. Would you ever think of remarrying or living together with someone 24/7? Sydney’s shaking her head no.

SYDNEY

No way. We are done. We’re done with the marriages.

LAURA STASSI

We …?

JENNIFER

However…

LAURA STASSI 15:49

Okay, so back up for just a second. I know you had a marriage to your high school or old childhood friend that went south. Was that …if you don’t min me asking, how many times you’ve been married?

JENNIFER

Do I have to?

LAURA STASSI 16:03

It’s okay. It’s okay. Believe me.

JENNIFER

Yeah. Well, actually, yeah, I’ve been married three times.

LAURA STASSI

Three times. Okay. That’s No, I mean, it’s cool. Sydney, is that why you’re saying that she’s done with the marriages, from your perspective?

SYDNEY

I think so. I think partnership and companionship, do you have to have a marriage to do those things? I don’t think so.

LAURA STASSI

Okay, so Sydney says that her mom is done with marriage. Jennifer, what do you say?

JENNIFER

16:35

I’m still open. As Sydney says, I am a hopeless romantic, as I will never rule out that that would not occur.

LAURA STASSI 16:48

I don’t want to stir up any trouble. But I do think it’s interesting that Sydney is 100 percent behind her mother finding romantic companionship. But she’s thumbs down on marriage. As for mom, Jennifer, she’s leaving the door open to tying the knot. I have to say, I respect her optimistic outlook.

17:10

Jennifer also says she’s happy with the dating apps she’s on now. But she may check out another one just to cover more bases. And while Jennifer was really nervous to put herself out there, she’s happy she took the plunge.

17:24

Next, we’ll hear about a widower whose reflections on marriage guided his daughter through her own romantic journey. That’s after the break.

BREAK

LAURA STASSI 17:42

If you like what you’ve seen with my headshots through the years, you can thank one of my college friends.

JENIFER

I’m Jenifer, 62 years old. Okay, Dad, so why don’t you say your name? You just say Herb.

HERB

Hi, this is Herb.

LAURA STASSI 17:58

Jen’s a professional photographer. Her 92-year-old father lives with her. Herb’s health is declining and speaking has become difficult. But Herb has persevered. And so, too, has Jen. Because living together, that was never the plan. Maybe it was bad luck, bad timing. Or maybe it was fate that brought Herb to live with Jen.

Now, this story has a few twists and turns. So let me start at the beginning with Herb and Jen’s mom, Jeri. Back in 1999, Jen’s parents moved from another state to a college town about 100 miles from Jen’s house. Jen’s married, has a little kid, and soon she’ll be expecting a second child.

18:45

Herb had recently retired from a long career. He and Jeri had sold a bed and breakfast they’ve been running, and they have plans to take advantage of everything their new hometown has to offer. But then Jen’s mom is diagnosed with a very aggressive cancer. She dies only a few months later, at the age of 64.

19:08

Of course Herb is grief-stricken — and stunned. They’d been in their new house for only a year. He’s still active and healthy. And after 39 years as a husband, he’s suddenly …  not. As a way to process his emotions and figure out a way forward, Herb starts thinking about his marriage and what had made it so fulfilling. He puts his thoughts to paper, and he types up a list. He titles it, “Requirements for a Successful Long-Term Relationship.” There are a total of 13 attributes on the list. Herb writes, they’re not in any order of priority, but it’s important for both partners to possess them to quote, ensure a successful marriage.

JEN19:58

Go ahead, take a nice deep breath so you have lots of air in your lungs. Okay?

HERB

Number one, strong self-image. I’m important and worth something.

JEN

I’m important and worth something. Two: an attempt by both partners to be non-judgmental. Three: strong sense of humor and the ability to laugh at one’s own foibles and not to take yourself too seriously.

HERB

Four, the self-confidence … let’s start again.

JEN

OK.

HERB

Four: the self-confidence that you can do almost anything and indeed, attempt it.

JEN

Great! That was good. The self-confidence that you can do almost anything and indeed, attempt it.

LAURA STASSI 20:44

Herb gives copies of the list to Jen and her siblings, Jen tucks it away. Undoubtedly, she recognizes that many of the attributes Herb cites are missing in her own romantic partnership. Jen’s marriage has been crumbling for a while now. She and her husband split up in 2002. And at the age of 40, and with two little kids, Jen’s on her own.

DAVID

Five: a spiritual underpinning. Even though I may question the existence of a god, I feel the presence of a force or power that interacts with something that is receptive.

JESSICA

Number six: a passion for intimacy and the desire to communicate it. Number seven: it is important that both partners not be prejudiced toward any group and never refer to a person by a derogatory name, and or stereotype description. Number eight: sensitivity to the feelings of others and not saying something for the sole purpose of degrading or embarrassing another. Number nine, the ability to compromise over differences and achieve an agreement in which neither partner feels that he or she has been ill-treated.

LAURA STASSI

That’s Jen’s brother, David, and sister, Jessica, reading from their father’s list. After Herb writes it, he reconnects with a childhood neighbor. She’s now a widow living in California. Let’s call her Marie.

Marie is about eight years older than Herb, but you wouldn’t necessarily know it. They start a long- distance relationship and eventually decide they want to make their love official. So they declare their commitment to each other in front of family and friends. That’s in early 2003.

22:34

Herb and Marie decide they’ll live half the year in her California home, near her family. And then they’ll drive cross country to spend the other half living in Herb’s home, near his family. For almost two decades, it works great. And then, it doesn’t.

DAVID

Ten: mutual respect for each other’s space and to recognize that sometimes, there’s a need to be alone.

LAURA STASSI 23:04

It’s almost time for Herb and Marie to leave California for their latest cross-country trek. But Herb’s driver’s license in his home state is expiring, and his house needs a little bit of work. Marie doesn’t like to fly. So Herb decides to make this quick trip without her to get those chores done. It’s all good. It’s one of his attributes. “Sometimes, there is a need to be alone.”

23:30

Herb packs a small suitcase and boards a plane heading to the East Coast. He arrives on March 1, 2020. No one could have predicted that days later, the world will go into coronavirus lockdown. Herb can’t travel to get to Marie, and Marie can’t travel to get to Herb.

23:50

At first, everything is as fine as it can be. Herb creates a pandemic bubble with his kids. Marie creates one with her kids. Herb and Marie talk on the phone every day. My friend Jen’s work has dried up. It’s a big financial strain. But the free time allows her to help her dad tackle some of those long put-off projects, like going through her mom’s stuff and cleaning up the garage.

24:17

And like her dad, Jen has re-partnered. She met Chris when she’s in her early 50s, through a cycling group. They’re practically neighbors, and they are very happily living apart together. Chris, who’s never been married, understands and supports Jen’s devotion to family.

JEN 24:37

Eleven: speak out as soon as possible about real or perceived problems, and not allow anger or frustration to build up. Do not let the sun set on any problem. Twelve, opinions and points of view different from one’s own are acceptable and will not give rise to the feeling that the other person is not supported.

LAURA STASSI

Months ticked by. Then in early July, after Jen and her dad return from a road trip to see sister Jessica, Herb has a stroke. For two months he’s in the hospital, in rehab. Afterward, as Jen says, the only option is for him to move in.

25:27

With home health aide and virtual classes with the Stroke Comeback Center, Herb is progressing well. Jen’s brother, David, arranges his work schedule so that he can make regular trips from out of town to help out. But then — you’re not going to believe this. I’m not making it up. A tree comes crashing down on Jen’s house.

 

They’re all inside: Jen, Herb, Herb’s health care aide, David. Thankfully, no one is hurt. But the family is displaced while major repairs are made. It’s traumatic and stressful. Jen is now juggling insurance claims, contractors, physical therapy appointments for Herb. It becomes more and more difficult for Herb and Marie to communicate.

26:14

And every time Jen and her siblings start talking about how to get Herb and Marie together, something inevitably arises to thwart the plan. Like April, a year ago. Herb falls and breaks a hip. He now needs around-the-clock care. It seems unlikely that he and Marie, who recently turned 100 years old, will ever again see or talk to each other in a meaningful way.

26:44

And Herb’s at the point of his very long life that I remember my dad experiencing a bit of shortly before he died at age 95. Herb’s looking back on his years and all the memories. He’s expressing some regrets. And he’s longing for the companionship and love that he once had in abundance with Marie and before that with Jen’s mom, Jeri.

27:09

As for Herb’s list of attributes, my friend Jen already knew instinctively that Chris possesses them. Still, she dusted off her copy so that her brother and sister could take turns reading it aloud at her wedding. After eight years of dating, Jen and Chris tied the knot. They had a small ceremony for family and then in October, they repeated their marriage vows during a Quaker worship service.

Jen and Chris are still living apart together. But for them, the ultimate expression of their unconditional love is marriage.

DAVID

Thirteen, the most important is the existence of unconditional love. For if this exists, most of the above will be achieved.

HERB

Most important is the existence of unconditional love. For if this exists, most of the above will be achieved.

JEN 28:09

Wonderful. Thank you so much, Dad.

END CREDITS

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I’m Laura Stassi. Thanks so much for listening.

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