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I'm Laura Stassi, and this is Dating While Gray, the grown-up’s guide to love, sex and
relationships. On this final episode of our first season, I'm sharing some advice I’ve found
especially insightful since becoming single.

Last summer, my old friend Hope came to town and we met for drinks to catch up. In fact,
when we met up for happy hour, she'd just gone through a very messy breakup with her
first love post-marriage. So we talked about that for a while, and then Hope asked how I
was doing. And that's when I said aloud for the first time that I was worried I was attracted
to someone who wasn't really available, at least not by my definition. Hope looked at me
and gently said, “If he can't walk in through the front door, don't let him in through a

Wow. A simple sentence that cut through the fog in my brain and painted a vivid picture of
what I already knew to be true. I needed that. And maybe it's corny or cliché, but I think
little sayings like this serve a good purpose. When I'm going through something really
emotional, like a strong physical attraction or a painful heartbreak, I really don't have the
brainpower to process advice that's much more complex than that.

So I can understand when people say things like “Time heals all wounds,” or, “If it's meant
to be, it'll be,” or “When you're going through hell, keep going.” And it can work!

But now that I've regained my emotional equilibrium, it's time to ponder some advice that's
a little deeper. In fact, sharing advice is one of the reasons why I really wanted to do this
podcast in the first place. Clearly, not any one person has all the answers. I thought it
would be really helpful to bring a lot of voices into the mix with the idea that maybe we'd
each find something that resonates -- that we'd want to explore further -- so we can figure
out next steps to make new romantic connections or get over those that for whatever
reason, don't work out.

You know, I call some of these voices “experts,” but that's because advice giving is part of
their profession. But I don't think you need to be an expert to have valuable insights,
especially when you've gained those insights the hard way: through personal experience.

Sophy Burnham is a writer at her body of work is deep and wide. She's written plays and
novels, nonfiction books, exploring art and angels and intuition. And a recent piece was an
essay for the New York Times's Modern Love column on sensuality and aging. So I was
really interested in talking with Sophy to get dating and relationship advice from her
perspective. She's in her early 80s, married and divorced once, and I figured she would
have a lot of wisdom to share.

So it was a surprise to me that I did not remarry because I thought that was what women


In spite of being very independent and very much a rebel, I'm also a product of my own
culture and my own culture said, “A woman is not herself sufficient. She must have a
It's taken me a long time to realize that this is one more of those unnecessary bits of
information like “opportunity knocks but once” that they tell you and is completely wrong.

You've been in love. Did you ever come close to living with someone or being in a another
committed relationship?

I've been in committed relationships. Mmhmm.

It just never got to the point where you wanted to…. Have you ever lived with somebody

Well, each one has its own story. One man that I was in love with, deeply in love with, and
he with me, was married and separated and after five years went back to his wife. That
was, but I certainly expected to marry him. He said to me, “I will marry you and I want to
marry you. I know I'm being difficult.” And then two weeks later, he ended up back with his
wife because he couldn't stand the pressure of a divorce and what it would do to the family
and everything. I understood.

I've been talking to a lot of women who, it seems like men, there are a lot of men out there
who are what I call “aspirationally separated,” that they, you know, they're unhappy in their
marriage, but they don't necessarily want to get divorced.

They can’t get out of it.

Right. For whatever reasons. But…

But dating is hell. Dating is really stupid. So don't look for a date. Don't look for a boyfriend.
I know many, many people who have gone on and they search. My gift to you
is this.


Find, don't seek. The universe will bring you the right person.

OK. I like that.

We spend much too much time wasting time trying to fill up something that we think we
need. If you love life, life will love you back. And it will give you what you need. And friends
are much better than boyfriends.


And there's a huge responsibility with boyfriends, right?


So the boyfriend you have now, do you anticipate ever wanting to live together or to live
with anyone?

No, no. My idea of heaven is to have a long-term, perfect relationship with separate
houses and especially separate bathrooms.

Oh, absolutely. Separate closets, too.

Of course! I mean, could you imagine sharing your closet? No!

No. You know, I have spoken with married couples who don't live in the same, under the
same roof.

I know it's a perfect solution. The other perfect solution is a friend of mine. They have a
completely open relationship in which they are free to have any sexual partners that they
wish. And then they come back and tell each other about them. And they are madly in love
with each other. And they have been in love and they have been married for 50 years.

Oh, interesting. Speaking personally, I think I would be too jealous to have an open

You have to have confidence in yourself as a sexual and sensual being.


I think the point that I'm trying to make is that I know women even today who believe they
are not enough without the protection of a man, without having a man not necessarily to
live with, but a man on your arm, as it were. And if you don't have a man now, enjoy this
minute completely, because when you do, you won't have this freedom.


And you probably have seen people dating people that are probably not worthy of them.
And their response is “Well, it's better than being alone.”

Yes that's exactly it! How is it ever better than being alone?

Well, so that's what I tell people. Better, being alone is…
I’d rather be alone with me!

Being alone is your ceiling, not your floor. For some people, being alone is their floor.

Is terrifying.

Yes, yes.

It’s terrifying because they don't know who they are.


And they don't like themselves enough to be their best friend.


You want to be connected physically, spiritually and emotionally. The age is not important,
but you have to have at least two of those and preferably three. I have many young friends
who don't understand at all that things come and go, that there is a change, that there's a
rhythm to life. And they keep trying to hold on to the, hold onto this. So that they're not
allowing the fluidity of time to make any changes. And they're the ones who are most


You have to live it lightly. Make a friend of him. Like him, before you fall in love with him.
And then be prepared to have a lot of tolerance and compassion and patience and
forgiveness, because relationships are really about seeing who you yourself are and the
other person is going to bring up before you aspects of yourself that you don't know that
you have. And sometimes these are really good aspects. And then you fall madly in love
with him. Until you have acquired that, integrated it yourself, and don't need him. And then
you will find it sifting away. And others of these aspects are things, parts of you that you do
not want to know at all.


And your task in the relationship is to discover who you are.

I can relate to what Sophy said about waiting for the universe to bring someone to you. It's
how I've approached it, for the most part. But I don't think her advice is about being
passive, because she says so much about changing your outlook and loving yourself and
your own company.
I checked in with Sophy recently, and I think the pandemic has added some urgency to her
perspective. Sophy told me people need each other and we should strive to couple up
because human touch is important and she misses it dreadfully. She says she can't
recommend online dating because she's never done it herself and has heard too many
bad stories from friends. But she did suggest looking into hiring a matchmaker. I think
Sophy's intrigued with how many people across time and cultures have used them.

Speaking of, I'll be talking with a matchmaker. That's after the break.

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Head to or click the link in the show notes. And thank you.

Leora Hoffman is an attorney who decades ago made a big career switch. She became a
matchmaker. And then while she was matchmaking for other people, she went through a
divorce. She thought it might wreck her business, but it survived and even flourished. And
eventually Leora got married again. She was in her mid-fifties when she walked down the
aisle with a man friends introduced her to. Leora’s coupled up a lot of people. So I wanted
to find out what she knows that the rest of us might not know. And why anyone would need
to hire a professional instead of just, you know, doing it yourself.

So before the shutdown, we met at Tysons Corner for lunch.

Well, you know the expression, “Physician, heal thyself?” It's hard! We don't have the
objectivity as human beings to be able to always know what's in our own best interests. So
it's very helpful to have an objective third party make recommendations where people
might not have thought of a particular type, for example. You know, people come to me,
they tend to be a little bit stuck in some particular patterns. And part of my job is to help
figure out what that pattern has been. And to encourage them to go beyond that pattern if I
feel that there's somebody well-worth meeting who's a different type of person for them. Or
offers them other qualities that they really hadn't thought about. So part of the intake
process is really about deciphering what people's needs are, what's negotiable and what's

So if somebody tells you, “Hey, I'm a tall woman and it's non-negotiable, I do not want to
date somebody shorter than I am.” How would you respond something like that?

I respect people's comfort levels and criteria, and I would tell that person, “I will note your
strong preference, and do my best to find you people taller than you, if that's your criteria.
However, I might suggest somebody to you who's two inches shorter, and I would hope
that you would be open-minded enough to consider that person.”

I myself in my single days dated a man -- I'm 5 foot 5 -- I dated a man 5'5”. I didn't like the
idea, but I liked him.


And I was willing to tolerate that little bit of discomfort on my part. Because…
As you got to know him…

As I got to know him, I was attracted to him, otherwise. I had a wonderful time with him
and I decided that I'm just gonna let that go. And it didn't work out for other reasons, but it
had nothing to do with his height.


People can sometimes make the mistake of thinking that after a first date, if I don't think
this is somebody I could marry, then well, then they're not for me. Relationships are a
continuum. They start with casual dating and hopefully if it's the right person, deepen into
something more substantive over time. But it takes time.

Yes. And dating is a lot of work!

It is it is a full-time job, which is why there's a need for someone like me, because not
everyone has that time. Many people would rather hire me to vet candidates for them and
make recommendations for qualified leads.

Are there certain mistakes people make?

I can give you a list of mistakes that people make. People project. I think that can be a
very self-sabotaging practice where somebody might meet someone on a date number
one and think, “Well, I didn't really feel as strong a connection as I would have liked, and
therefore they're not somebody I could ever see falling in love with.”

I've seen situations that evolve very slowly. It might be a while before a physical chemistry
kicks in between people. It happens in so many different ways. Sometimes people meet
right away and they're off to the races and they know it. And that's fabulous. Those home
runs do happen, but they're rare.


Most of the time it's a process and I have a lot of respect for the process. And I think one
of the other mistakes people often make is impatience, where they want to know. They
want to know, is this going somewhere? Well, sometimes you can't know until you're in it
and you spend the time and you invest the energy to figure out who this person is and
whether you can really communicate with them effectively and whether they share the
same values as you. That takes time!

Do you have any interesting stories you can tell whether it was a long-term relationship or
just a, you know, a great-five-months-kind-of-a-thing?
Oh, I have so many stories.

Beautiful woman, divorced, two grown children. She had met some everyone in her age
group in her area, pretty much, had exhausted that pool.


Or so she thought and decided that she wanted to look beyond her geographic area and
because her children live here, in the Washington, D.C. area, she felt like if she met the
right person, she could easily relocate here. So I introduced her to a local person and he
drove up to Philadelphia for the first meeting. They hit it off beautifully. The first date was
lunch and they spent almost six hours at lunch.

Oh, my gosh.

And she came to this area. They seem to be smitten with one another.

Oh, how lovely.

And he's now invited her to his beachfront property in North Carolina for a long weekend.
So we spent a lot of time talking about how to manage that and whether the timing was
appropriate, whether it was too soon, what to look out for. Part of what my job is when I
work with someone is really to coach them. I did tell her I would have waited a little longer
to really take that step. But if you really feel it's right, make sure you communicate your
needs very clearly and make sure you don't do anything you're not comfortable with.

Is there anything else I need to know?

Well, just that love is a wonderful and, you know, challenging process to achieve. It takes
time. It takes patience. It takes dedication. I'm a I'm an optimist. I feel that it's possible at
any age. And I think that as we get older, our needs are stronger for companionship and
for connection.

Leora has been a matchmaker for a long time. No doubt she's seen it all. So I think it's
especially valuable that she suggests considering people who are not our usual type and
also giving someone a chance beyond the first date or two. People can grow on you.

Another source of advice? Anyone who's ever gone out on a date. Over the past few
months, I've been asking you for your advice to share your stories. And here are some of
my favorites.

Hi, it’s Albert Kaufman from Portland, Oregon. I’ve been thinking about organizing
something called “Speed Friending” where people can find friends in the neighborhood. I
think really we all want more companionship. I think even just people are missing out on
having more close friends in their lives. So thanks so much for your show. I'm really
enjoying it. And good luck with love! Thanks again, Laura, bye bye.

I heard some of your episode about you’re interviewing some other women and men and
they’re saying, “I like this” and “I like that” and “I like this.” I thought that it's a good idea to
hang out with people who like doing things that you like doing. Because if you already like
doing something, it's not such a big step to do it with someone else.

Hey, my name is Mary Pat Hinders. I am calling from Raleigh, North Carolina. I am in the
position of 30 years of no dating after a very difficult marriage and trying to get back into
the swing of it. I need to get some experience of having some dates. My counselor keeps
encouraging me, “You just need practice. You need to practice, and to get practice, you’ve
got to go on dates.” Thank you so much.

Hi. My name is Sharon and I live in San Antonio, Texas. My situation is such that, yeah, I
am single now and I don't really want anybody in my life because I'm healing from a past
relationship I was in, that my heart got broken. Something that's mending my little broken
heart right now is I have a puppy and we're figuring stuff out together. So I just have to
wait and see and figure stuff out. All right. Thank you!

Hi. I'd love to be anonymous for this. I was divorced four years ago, spent that time very
meticulously searching, but at the same time truly enjoying my life. And about seven
months ago, found the next love of my life, no question about it. But it was very interesting,
the process. I don't know if I have anything specific to offer except that I made a plan. I
stuck to it. And then after being on every dating app and working very hard at it, the love of
my life ended up being practically across the street. Thank you.

Thank you, listeners. We are all in this together, and I hope as soon as the COVID-19
coast is clear, we're all going to put some of this advice into action.

Finally, we'll hear from a woman who's made a career out of advising people not only how
to make romantic connections, but how to peacefully end them. That's next.

Are you following Dating While Gray on Facebook yet? I'm posting stuff to keep me going
while working from home. You can get updates as soon as you log on to Facebook by
searching for Dating While Gray and liking our page.

Remember when Gwyneth Paltrow and Chris Martin announced they were getting a
divorce, but they didn't say divorce, they said they were conscious uncoupling? Raise your
hands if you rolled your eyes. I know I did!

But then I read the book, Conscious Uncoupling, by marriage and family therapist
Katherine Woodward Thomas. It's just a coincidence that when Gwyneth and Chris made
their announcement, Katherine was writing her book. It was about her own divorce.
Katherine had also written a book about finding the husband she then divorced. That book
was titled Calling in the One: 7 Weeks to Attract the Love of Your Life. And it was a
bestseller. Millions of people turned to Katherine for advice.
So was her husband not really the one? And did she have any second thoughts about the
advice she was giving? I asked her about it, starting with the moment she decided to set
an intention to find a partner.


Well, I'd been single for decades. I was in my early 40s, so I was kind of a true-blue card-
carrying member of one of the fastest growing demographics in America, which is the
never-marrieds. And I was not happy to be in that group. I had wanted a family since I was
really in my early 20s, but I had had a lot of relational trauma in my early life. And that
followed me then into very unstable relational patterns. I knew my issues backwards and
forwards, inside out. And still this really painful pattern of unavailable people were showing
up for me.

Unavailable? How?


Oh, married men were always coming on to me, you know, engaged men, alcoholic men,
you know, any kind of impossible love, any size, shape or form. That was my throughline
for all of it. And it felt like it was just happening to me against my will. It felt like my fate to
just be alone, that no one would ever really be there for me.

So what happened that changed the game for me, Laura, is that I started to understand
the power of setting an intention and living into a future that was unpredictable and kind of

So you set this intention and then what did you do?


So I began to look at the places within myself where I was pushing love away or
sabotaging love outside of, you know, outside of awareness. The parts of me that were not
it in integrity with that future, not aligned with that future. So I’d started with the basic
questions like, “Well, how is it working for me to be single?” and “What's the part of me that
doesn't want to be in relationship?”

So you start asking questions like that and all of a sudden I started to see the parts of me
that didn't want to be dominated by someone else's agenda or the parts of me that loved
my freedom. And then I asked a series of questions: “What would I have to give up to
manifest this future?” And I would sit with that question and really just listen to my gut.
Next question: “What would I have to begin to cultivate? How would I need to grow myself
in order to prepare myself for that future?” And then I'd listen to that for a while and
contemplate on that question. And then I would ask the final question: “What's my next
step that I can take today?”

How did you actually meet the man who then became your husband?


So I was doing this very deep kind of internal work. A few months, or a few weeks in, in my
meditation, I started thinking about this man I had dated six years earlier who I always had
thought of as the one that got away.



Handsome, kind, educated, successful, you know, fun to be with. So about a couple of
weeks after this started happening, I went to a church service. Now, I'd been going to this
church for 10 years by this time, I'd never seen Mark there. And lo and behold, I'm in
between services and there's all these people milling about in the parking lot. And I look up
and there is Mark…



…across the parking lot. And I had a shy attack! And I did not go speak to him! And by the
time I gathered my courage, he had left. But one of the things my friend told me to do was
to get online.

Online dating?


Online dating. Now we are going back, Laura, 21 years.

[laughter] I didn’t know they had it back then!


It was just the beginning! But nobody had their picture up.



Very few identifying characteristics. I, I gathered my courage again. I was coachable. I did
what my friends suggested. And I found a quarter of a million people on this site. And I
narrowed it down to about 80 just by putting in that I lived in L.A. and that I wanted
children. And what my age group was and all that stuff. But again, no identifying

But I start reading through these profiles that these men had written about themselves.
And one of them really captured me. I liked what he said. He sounded like a well-rounded,
happy person. So I wrote to him completely anonymously, and he was the only one I wrote
to. And the next day when he wrote me back, the technology back then was such that it
came right into my email box. And his name was next to his email address and it was

Oh, my gosh.



Now, I would tend to think that you were meant to be together. So long story short, you
end up dating him and getting married and you met your deadline. Correct?
I came in two months ahead of deadline and then I had my first baby at the age of 43.

Oh, my goodness. So…


So I really was living happily ever after. And then I thought, “Wow, this can't be a personal
miracle. I have to share this with people. And that that was what my first book was, was
Calling in the One.

You called in THE ONE. You wrote a book about it. And then?


The spoiler alert is that we ended up getting divorced after a decade.



And I was able to do that in a beautiful way, even though I think it was, you know, it’s
always devastating. It's always a shock. None of us ever think when we're walking down
the aisle to pledge lifelong devotion to our one true love, that, you know, we will one day
wind up on the wrong side of that divorce divide.

I'm wondering, you must have felt a little hesitation. You wrote about him as The One and
he's not The One. He was…


Yeah. Well. Well, he was, though. There's a point. There's a point we get to where we say
“I have to live an authentic life and let the chips fall where they may.” And if it means I lose
my platform, I lose my audience, then then I will be sad for that. But I have to be true to
myself. I have to be true to Mark. I have to be true to our relationship.

So I did choose that. But I will tell you, on the day that we decided to, that this was really
going to happen, that I went to the park where we'd go and just walk around and
contemplate a lot. And I lay down on the grass. And I looked up at the sky. And I prayed
the only prayer that made any sense to me at the time, which was, “You have got to be
kidding me.”

I'm getting chill bumps. I think all of us…



…who have been in love relationships have kind of felt that. I mean, but the irony. The
irony! Did you consciously decide that “We’re going to make this a loving process?” Or
was it just in your nature to make this as pain-free and loving as a split can be?


Our daughter was our biggest concern. So we were able to align. I remember sitting in the
living room talking about that this was indeed going to happen. But pretty quickly, we
aligned on a shared agreement that we were gonna make sure our daughter had a happy

Did the fact that the marriage ended in divorce, did that change anything about Calling in
the One?


Well, I think, you know, for a while I went through a period where I wanted to not teach it.
So I didn't share it publicly right away, not because I was trying to, you know, salvage my
brand or pull one over. But I had to really think about, I wanted to be through it myself so
that I wasn't coming into sharing with students things that I was still dealing with that
weren't complete for me.

I never stopped believing in Calling in the One. What I did is I started to hold more
complexity about it. And I started to research the happily ever after myth because I
realized that, you know, when we if when we end a relationship, most of us feel a sense of
shame and failure about it. And so I realized, I asked myself one day, “Well, whose
standard am I holding myself to?” Because if I really look at, you know, why we made the
decision to separate, how we separated…there's a lot of integrity in it! So the shame does
it really make sense? So whose standard am I holding myself accountable to? And I
realized it was really the happily ever after myth. We just assume that a relationship should
last a lifetime.

The thing that really, I guess, resonated with me is: I used to think I had to fix my ex-
husband. Or, you know, why would he want to leave this marriage? This marriage is fine!
You know, why would he want to leave? I need to fix him, so that he doesn't want to leave
the marriage. And I realize after reading your book -- thank you very much -- that it is okay.
It is okay that the love died. I mean, it's hurtful, and it's best to, when that happens, to end
the marriage kindly and carefully, but that there's no, what you said: that there's no shame
in being the one who wants to leave. And so I should not… I should forgive him and
forgive myself for that. So, thank you.


Yeah. I tell people, if they're not sure if they want to stay or go. That they can do it, to
uncouple from the dynamic as they've known it.



And recreate, really stand for re-creating a different kind of connection without being
attached to whether they're married or unmarried.

Do people sort of need to Conscious Uncouple from their past, whether they're divorced or
widowed, do we need to do that in order to call in the next one?


If we don't want to carry the baggage of our unfinished business into the next relationship,
that we would do well to really put things to bed and really do our deeper reflection work to
be, to come to a place of total peace. And having learned our lessons and having grown
so that we can trust ourselves to not make those same mistakes again with someone new.

Mmhmm. And…


I also say that our next relationship won't begin when we meet our next partner, but with
how we end with this one.

I'm hearing from some people who say, you know, they're doing everything. And they just
can't connect with someone. They can't find someone. Do you have, you know, some very
quick advice, what might be going on that they're not having success?


If the complaint is “I'm not connecting with someone,” I might help someone to really
deepen into their own connection with themselves and then begin to speak more
authentically from there. A lot of my work is about, you know, profound levels of self-
responsibility in a way that really reveals how much power we have in a relation, in any
relationship, in any given moment, to actually create that which we say is missing.

Katherine has a program. She trains therapists across the country how to help their clients
Consciously Uncouple or Call in the One, maybe sometimes both. And Katherine has
called someone new into her own life. She says she and her sweetheart have been
sheltering in place together.

I really found the book Conscious Uncoupling helpful. It led me to understand that the end
of my marriage was not a failure, and that I needed to let go of the anger and the
resentment along with the romantic relationship so I could move forward in my own life.

You know, I've learned so much in these past few years, but especially since I started
doing this show. But I do understand I'm not done yet! I did buy a Calling in the One
workbook. And let me tell you, it's thick. It'll take me a while to get through it.

But I'm going to have some time on my hands now that we're wrapping up the first season
of Dating While Gray. You won't be hearing from me for a little while, but you can stay in
touch through the Dating While Gray Facebook page.

And as we end this first season, I want to thank everyone who shared their stories with us:
Amy, Ann, Arthur, Beth, Blair, Bob, Brett, Colette, Debbie, Dennis, Diane, Elaine,
Evamarie, Girard, Giselle, Jamie, Jeanne, Jen, Jenevieve, Jim, Joani, Kathryn E,
Katherine T, Ken, Leora, Leslie, Marge, Mark, Maxine, Michael, Michele, Norm, Robert,
Robin, Sandy, Sophy, Steven, Susan, Whitney

And thanks to you for listening and writing and calling. I feel really proud that we've built a
strong and supportive community for Dating While Gray.

Dating While Gray is produced by Poncie Rutsch, Patrick Fort, Ruth Tam, Julia Karron and
me, Laura Stassi. Our theme music is by Daniel Peterschmidt and Mike Kidd mixed this
episode. WAMU’s general manager is J.J. Yore and Andi McDaniel oversees everything
we make. We'd love to hear from you. Send an email to, or
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donation at I’ll miss you. Thanks for listening.