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I'm Laura Stassi, and this is Dating While Gray. The grownups guide to love, sex and
relationships. On this episode, stories of facing a brand new day.
I have a confession. These past few weeks for me have not been so very different from
how I spent the six weeks before COVID-19 forced us all to stay away from each other. In
those six weeks, I was working so hard to get this podcast off the ground that pretty much
all I did was work. And when I wasn't working, I was walking the dog, so I wasn't doing any
of the stuff I would normally do every week. I wasn't going to bars or restaurants. I wasn't
meeting up with my running group on the weekends, wasn't going to my yoga studio,
wasn't going to church. I still have plenty of work to do and the dog still needs walking. But
there's something about not being allowed to do all that other stuff that's made me really
think about how I've been living my life, and I'm starting to feel like I've been wasting
precious time that I could have potentially been spending with a special someone. I'm not
beating myself up and I'm striving to not feel anxious, but I am giving thought to figuring
out a plan for my life, not only for when it's safe to mix and mingle with other people, but
right now what can I do to keep myself motivated to potentially make new connections? It's
a brand new day.
Someone who knows what it's like to face a brand new day is Maxine. She's in her early
60's and lived most of her life as Max, a self-described alpha male. Max had lots of
girlfriends and was married three times, but Max was restless and could never figure out
why. It was toward the end of Max's third marriage, when unexpectedly things just clicked.
MAXINE
I was dating someone that was very adventurous.
LAURA STASSI
OK, hold on. You were married?
MAXINE
Yes.
LAURA STASSI
So you were dating someone or were you having an affair?
MAXINE
Well, we could go. We'll say dating someone.
LAURA STASSI
Wait a minute. My definition is if your wife knows, if your current, if you were married at the
time. So if your wife knew you were dating her. If your wife didn't know you were having an
affair.
MAXINE
I was having an affair.
LAURA STASSI
No judging, just, just wanted to make things clear. Yeah. No judgment at all.
MAXINE
And so she said, "I'd like you to dress up as a girl." And I'm like, “sure, I'm comfortable with
my own sexuality," stuff like that. So she was a little petite thing. So nothing fit. So I met a
lady online who was my size, who is now my best friend, and she just had lots of stuff to
sell. I went to her house and I bought a bunch of stuff and she said, "have you ever been
dressed up?" I'm like, "nah, my girlfriend wants me to dress up." She goes, "look, let's just
make you up." So put all the clothes on. She did all my makeup, got the hair on, got it all
fixed and turned me around in the mirror. And that was the answer to every question I've
ever had in my entire life.
LAURA STASSI
Wow. What do you mean by that?
MAXINE
I used to race motorcycles, drag race cars. I've raced stock cars on a big level, ARC and
NASCAR. Won championships, jumped out of airplanes. I'd get to the pinnacle, achieve
what others couldn't and go, "eh, this is nice. Let's go home." And kept searching and
searching and searching. You spend a lot of time just doing, you know, type A personality
stuff. You know, you walk in a room, you take control of the room instantly. People see it.
It's just how you are.
LAURA STASSI
And how about the girlfriend that suggested this was she? How did she feel about this?
Cause it seems to me there might be a difference between wanting your "man," I put that
quote marks, you know, wanting your man to role play.
MAXINE
She loves it.
LAURA STASSI
Oh, OK.
MAXINE
I mean, we're, we don't see each other. She got a job and moved out of state and stuff.
But we're really good friends. We talk all the time.
LAURA STASSI
It sounds like you almost immediately embraced the new you. It wasn't like you had any
struggle, or did you? Did you have any?
MAXINE
I had no, no struggle, none, which lot, lots of girls do. There's two scenarios. You either
know at a very young age and you fight this all the way through your life, which is horrible.
Or there's the ones that later in life just sort of figure it out. Like myself and you know, and
and most of my life I'd been looking trying to figure out, well, what's gonna make me
happy, what's this thing? And a way I determined that this is the correct thing for me is, is
that I quit doing everything else that I did. I haven't raced a car, rode a motorcycle done
any of the, you know, skydived, any of the stuff that I did before. I just don't do. I'm, I'm
Maxine. And that's what I enjoy doing.
LAURA STASSI
Do you think there was something about being older that, that led to your being able to
make this transition, or did your understanding of gender identity change?
MAXINE
My understanding of gender identity changed just shortly before Caitlyn Jenner came out,
and then literally just I mean, I looked in the mirror and all the gears and clocks all lined up
and it was like, yup, that's what I should've been doing all along.
LAURA STASSI
And I think people do get gender identity confused with sexual orientation.
MAXINE
That is correct. Gender identity is who you go to bed as. Sexual orientation is who you go
to bed with. The way I describe it is here's 52 cards. Pick one. You're always right. Cause
there's just lots of choices, you know?
LAURA STASSI
As a woman, is it more difficult to. I don't know. Get somebody's attention if you need help
or you know, I'm thinking when I go and talk to a repair person, I feel like they're talking to
me like, "oh, you know, little lady, is there a man in the house" kind of a thing?
MAXINE
I think my personality's still big enough that that doesn't happen. I have no problems
navigating anything, going anywhere. I have been in a bar one time and I had a guy
messing with me. And.
LAURA STASSI
What do you mean by messing?
MAXINE
He was kind of being a little derogatory and saying some stuff. And the bartender leaned
over and goes, "don't let the hair and the high heel fool you. That used to be a man." And
the guy like, yeah, so.
LAURA STASSI
So it sounds like when you were a man, you were always coupled up. You had three
marriages. You had a girlfriend. Can we talk about your relationship status today?
MAXINE
Let's just attest. Yes, we can. I'm in a polyamorous relationship with a woman and we're a
committed couple.
LAURA STASSI
You're in a polyamorous relationship with a woman?
MAXINE
Correct.
LAURA STASSI
So just, can, for, define polyamory.
MAXINE
Polyamory is the ability to love more than one person at one time, and it forms in many
levels. Some are play partners. Some are committed couples that, you know, have, really
have a deep love and connection and want to have some sort of life together. It gets
complicated because generally polyamorous couples wind up having other partners. I
don't at the moment have another partner, but my girlfriend is married. She has another
partner and then her husband has I think three partners.
LAURA STASSI
I have a hard time with jealousy, so I can't even imagine dating more than one person at a
time.
MAXINE
There's, you have to embrace the term compersion.
LAURA STASSI
Compersian?
MAXINE
Compersian is a polyamorous word. And it is where you are happy for your partner's
happiness.
LAURA STASSI
That sounds like way too open hearted for me.
MAXINE
I mean, you know, I mean, like, you know, I mean, I've I've asked my girlfriend many times,
you know, she's been out with a date on her girlfriend, spent the night. I'm like, "hey, did
you have a good time?" Like "yeah, we had a great time." You know?
LAURA STASSI
But you don't live together.
MAXINE
No, we do not.
LAURA STASSI
So you live by yourself. And you used a term with me on the phone that instantly, I knew.
You used the term nesting partner.
MAXINE
Right. It's a description of the person you live with. It's a polyamorous term.
LAURA STASSI
Do you want a nesting partner?
MAXINE
I think so. I think I'm at a point in my life that my transition has gone you know, along far
enough to where I'm sort of settled into what it is and I'm not a spring chicken anymore.
And, you know, sometimes it's a little lonely.
LAURA STASSI
Even in the polyamorous relationship?
MAXINE
It isn't like I have all her all the time.
LAURA STASSI
So what are you looking for in a nesting partner?
MAXINE
Somebody you have a deep connection with. It really has to be, you know, on that level
that you know, that you trust that you really care for. I'd say you really have to love them
really well and deeply. It isn't really a physicality thing, but, you know, generally really good
lines of open communication where you spend a lot of time discussing a lot of stuff is real
good.
LAURA STASSI
And really hard to do whether you're in a polyamorous relationship or not. Communication
is tough.
MAXINE
When you have two people that are that, or three, or four whatever, that are in that
embrace polyamory and have studied it and go on ahead and understand the principles of
it, discussion and compromise are a huge thing. And it tends, it tends to work out well.
LAURA STASSI
You find it easier to?
MAXINE
Sure, because the person you're talking to is expecting you to go ahead and tell them
things that they might not be comfortable with. And rather than blowing up and losing their
cool, they're like, "well, you know, that's, that's a hard no for me. And I really, I can't go
there. Let's discuss in what we can work out."
LAURA STASSI
What's more important for you right now? Do you want to find a person to, you know, a
relation, to have a relationship with? And if they don't want to be polyamorous would you
be open to giving up the polyamorous lifestyle to be in a relationship just with one other
person?
MAXINE
No, because it would be, it would be a lie.
LAURA STASSI
Oh, OK.
MAXINE
I am not able to honestly be monogamous. And if the person expected that, that would be
hurtful to them.
LAURA STASSI
Mm hmm. And you're attracted only to women?
MAXINE
Well, we're on this podcast. I do like men.
LAURA STASSI
Were you interested in men when you were a man?
MAXINE
No, not at all. Was not interested in men till before hormones.
LAURA STASSI
Tell me about that.
MAXINE
That is an amazing situation.
LAURA STASSI
The hormones?
MAXINE
Yes.
LAURA STASSI
Oh, you like the estrogen, huh?
MAXINE
I love estrogen.
LAURA STASSI
I miss my estrogen.
MAXINE
Yes. Estrogen does wonders to the male body. And it's interesting how little you have to
put on, on the seesaw to tip the scale.
LAURA STASSI
So no regrets?
MAXINE
None. None at all. I well, the regret, yes. I wish I woulda figured this out earlier.
LAURA STASSI
My interview with Maxine was in early February and I called her just a few days ago to
catch up. Like a lot of us, Maxine is feeling stressed. Her business is suffering. The
transgender women's conference she was looking forward to is on hold and she hasn't
been able to get together with her girlfriend. Maxine says they're keeping in touch through
phone calls. But Maxine doesn't want to do any video chatting because she thinks it would
make her feel worse. But when I told Maxine that's a good excuse to not worry about doing
your hair or putting on makeup, Maxine told me visual presence is still important, even if
you're the only one who knows how great you look. After the break, writer Leslie Morgan
Steiner's brand new day.
Dating While Gray would not be possible without support from you, our listeners. That
means going to WAMU.org and clicking donate. We're dedicated to putting out episodes
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show us your support. And thank you.
Leslie Morgan Steiner has written four books. Two are memoirs about her two marriages.
Her first marriage was to a very abusive man and it took a lot of courage for Leslie to
leave. Her second marriage lasted 20 years and in many ways she needed courage to end
that one, too. Leslie's memoir, Naked Truth, talks about facing life as a newly single 50
year old and reclaiming her identity as a sexual being. I wanted to talk to Leslie because I
read Naked Truth and was really impressed with how easy she made it seem to make
romantic connections. We talked in December and I began the interview by asking if she
felt any pressure to stay married that second time. After all, there was nothing horrible
going on.
LAURA STASSI
Oh, my.
LAURA STASSI
Oh, ouch.
LAURA STASSI
Oh well, hello?
LAURA STASSI
Okay then.
LAURA STASSI
Your severance.
LAURA STASSI
How long after the split did you start thinking, you know, how long did it take before you
thought, "I need to get myself back out there?"
LAURA STASSI
And how did you ascertain all of this?
LAURA STASSI
And in case anybody doesn't know, and we're not gonna use the entire, mother, I'd like to.
LAURA STASSI
So it was spelled out that you had.
LAURA STASSI
And that was OK with you, that you weren't necessarily looking for a relationship. You just
wanted to.
LAURA STASSI
You just wanted to be an, a MILF.
LAURA STASSI
Were you then or are you now looking for a committed relationship? Or are you fine with
just meeting men and having sex?
LAURA STASSI
The thing I have found hardest is where do you meet these guys? I mean, I you know, I
belong to a running group. I go out to the movies. I go out with my friends. I go to a church.
I feel like either just out of habit or maybe nervousness, I don't scan the room, so to say
speak. You know, I'm like OK, I'm there to do this. I'm gonna sit there. Tell me what to do.
LAURA STASSI
After our interview, Leslie and I hit the streets of D.C. so she could show me how to open
my eyes to the possibilities of making romantic connections. That's after the break. \
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We're back, and Leslie and I are outside at the WAMU studios.
LAURA STASSI
Yeah.
LAURA STASSI
Yes.
LESLIE MORGAN STEINER
The yes-no game.
LAURA STASSI
OK.
LAURA STASSI
Uh-huh.
LAURA STASSI
Yup.
LAURA STASSI
Because you said you don't.
LAURA STASSI
OK. So it's an automatic no.
LAURA STASSI
Even though I'm thinking oh, he's kind of attractive.
LAURA STASSI
With women.
LAURA STASSI
Okay wait a minute, here's two more.
LAURA STASSI
Yes. No.
LESLIE MORGAN STEINER
No.
LAURA STASSI
You had it.
LAURA STASSI
Yes.
LAURA STASSI
Yeah.
LAURA STASSI
Yeah.
LAURA STASSI
OK.
LAURA STASSI
Wait a second. You got one on your right.
LAURA STASSI
Yes.
LAURA STASSI
Yeah.
LAURA STASSI
No. Too young, too skinny.
LAURA STASSI
For me.
LAURA STASSI
Yeah.
LAURA STASSI
Well, yes, but he's so young.
LAURA STASSI
Leslie, you bring up a great point because I am too focused, I think, on, "is he the one?"
LAURA STASSI
Yeah.
LAURA STASSI
Yeah.
LAURA STASSI
Yeah.
LAURA STASSI
I've got two no's here.
LAURA STASSI
OK.
LAURA STASSI
OK. See, I'm having a hard. OK. I really need to retrain my brain.
LAURA STASSI
Because I'm looking at, "husband? No."
LAURA STASSI
Yes. OK.
LAURA STASSI
Yes, do you like beards? That might be a, oh. That one's a no with that beard, going down
is a yes.
LAURA STASSI
Yes.
LAURA STASSI
Okay.
LAURA STASSI
Okay.
LAURA STASSI
Alright, no, that's good.
LAURA STASSI
Yeah.
LAURA STASSI
OK.
LAURA STASSI
OK.
LAURA STASSI
No.
LAURA STASSI
I don't like the way he's holding the bag.
LAURA STASSI
Is that weird?
LAURA STASSI
He was clutching it like.
LAURA STASSI
Yeah.
LAURA STASSI
Like I'm a stalker? But only because I've got equipment. So I think it looks weird. Plus, my
eye is dripping and my hair is flat.
LAURA STASSI
I mean I feel like I'm a big old mess right now. I don't feel like my best self.
LAURA STASSI
Well.
LAURA STASSI
Oh, I would be a yes?
LAURA STASSI
Oh, thank you!
LAURA STASSI
You would be a yes too.
LAURA STASSI
Okay.
LAURA STASSI
OK.
LAURA STASSI
It's a yes. Except for the bow tie.
LAURA STASSI
He's a yes. Hello? Excuse me, sir? Hello? Well, it would be a yes. He just, he's not paying.
LAURA STASSI
Totally absorbed in his phone. Yes. Hi.
LAURA STASSI
That's a no. Hello.
LAURA STASSI
No, yeah.
LAURA STASSI
Absolutely. Absolutely. Hi.
LAURA STASSI
I want somebody to say, "hi" back.
LAURA STASSI
Oh, oh.
LAURA STASSI
Ehh, maybe.
LAURA STASSI
OK.
LAURA STASSI
No.
LAURA STASSI
Hi.
LAURA STASSI
So I got an A for effort and instincts from Leslie, but I didn't end up doing this again on my
own. And now I can't. But boy, you better believe as soon as it's safe to get back out there,
I will be out there. As for Leslie, I checked in with her recently. She social distancing at
home in D.C., has a handful of men friends she's keeping in touch with. But she says that
now she's really interested in a long-term relationship. So she's mainly focusing on herself
and what she wants and needs in a long-term partner. So she'll be prepared when it's safe
to get back out there.
Now, I'm not giving up on making any connection, even though we all know how tricky that
would be right now. I want to find some alternatives to keep us going, especially after I
heard from a listener named Nancy.
NANCY
Hi, Laura. My name's Nancy. It's one of the last days of March. And I was listening to a
couple of your podcasts while I was cleaning my kitchen and a lot of the stories ring true. I
wondered if you would do a story about being alone, being solo during the pandemic and
how for those of us who have decided that we probably are permanently single, whether
we like to be or not, how that removes the idea of that spontaneous cute-meet meeting
and the idea of social distancing as another barrier towards becoming a couple rather than
a single.
LAURA STASSI
So I asked you, what are you doing to connect with other people while we're physically
distancing?
MICHAEL
Hey, Laura, this is Michael calling from Richmond, Virginia. And my wife and I were
separated for a while and are now cohabitating in kind of this interesting times during the
COVID staying in time. And it's been interesting. I think the one thing that's gotten us
through this so far, although it's still potentially early, is trying to just be very loving and
forgiving of each other. I am trying extra hard to do that and try not to be too wrapped up
around small things. And that has definitely been helpful. We are both work from home
now, and that's been certainly an added stress. The house feels smaller right now and I
like my space. So when this is all over, I do look forward to returning to having some
space. But I do look forward to looking back and saying we handled the stress well and
that is a good thing. Thanks very much, Laura, love your show. Take care.
LEORA HOFFMAN
I'm Leora Hoffman and I'm a matchmaker calling with advice during this pandemic. E-
mailing is preferable to texting because you give people an opportunity to express
themselves thoughtfully. You get to see how they articulate themselves in writing and the
recipient can respond at their own pace after reading and digesting the contents of an e-
mail rather than through a text where an immediate response is often expected. Number
two, phone calls. Psychologists tell us that hearing someone's voice is appealing to the
other person, actually produces the same endorphins as being in their presence. And
finally, Face-Timing or Zooming, whatever platform you may have. This certainly beats
getting in your car, going to a location, parking, spending money on a date and commuting
home. The search for love is not put on hold during this crisis.
LAURA STASSI
I actually did try to sign up for a virtual speed dating event, but by the time I got around to
it, all the spaces for women were taken, but it was still open to men. So I told my friend
Robert about it. He signed up, and the next day I called him for the details.
ROBERT
When I go into these things, I wonder how can you close the gap between expectations
and reality? And I think that gap in that between expectations and reality in this case is
very wide, very wide.
LAURA STASSI
Tell me about what you did.
ROBERT
Well, you signed up, bought the ticket and then you got invited through a set of e-mails to
go ahead and join the Zoom meeting. There was a moderator of the meeting and she
helped guide everybody into the dating rooms. Generally was pretty well organized.
LAURA STASSI
So did you only see people one at a time, or was there any point where you could see
everybody else who was out there?
ROBERT
Initially you saw everybody else who was out there.
LAURA STASSI
So you were able to also see the men that were participating as well, correct?
ROBERT
I did. I took a look at the competition, so to speak.
LAURA STASSI
And?
ROBERT
I was not that impressed.
LAURA STASSI
So you thought your chances were pretty good?
ROBERT
I thought they might be OK.
LAURA STASSI
How did you start each conversation?
ROBERT
Good question. Sometimes I started out offering up a short description of myself, myself.
Sometimes I asked them to tell me about themselves.
LAURA STASSI
Did you wear pants?
ROBERT
I did, yes. Video is tricky. You have, I think you look older and you look overweight on
video, and that doesn't help when you're dating while gray so to speak.
LAURA STASSI
Right. So, and this group was for 40 and up, right? It wasn't just.
ROBERT
That's right.
LAURA STASSI
So there were significantly younger people there?
ROBERT
There were. And I met a few of 'em. But really just one that was, I'd say, the most
significant younger and attractive woman I've met ended the date prematurely.
LAURA STASSI
Oh.
ROBERT
And canned out of the date, said she had to go to the restroom and left the date. No, that
was not a good sign.
LAURA STASSI
Ouch!
ROBERT
Yeah, that was an ouch.
LAURA STASSI
So overall, are you happy you did it? Did you? Well, first of all, is there anybody you met
that you would like to follow up with?
ROBERT
Not really.
LAURA STASSI
Oh. Now, will your mind change if somebody follows up with you?
ROBERT
Maybe. I sort of doubt it. I think I blew some of my introductions.
LAURA STASSI
What do you mean?
ROBERT
I just came off maybe too much like myself. But I think it all goes to this gap in
expectations, in video and media. Anytime you are not staged properly, you can look a
little off the mark.
LAURA STASSI
Gotcha.
ROBERT
And if you go and show up without a collared shirt, hair messy, every blemish showing
because the lighting isn't right, you will get probably zero interest, I'll tell you that. Some
people use backgrounds, which I thought was helpful.
LAURA STASSI
Oh, like what kind of backgrounds?
ROBERT
You put the right light. Beaches, cities, condos.
LAURA STASSI
Oh, that's a great idea. So this, if I'm hearing you correctly, you're saying this is not as
good as meeting somebody in person, but.
ROBERT
Probably not.
LAURA STASSI
Yeah. But during this weird time that we're on, is this better than nothing?
ROBERT
You know what? For this time, it probably is. Hopefully cabin fever hasn't gotten to me. I
had a vacation right before this.
LAURA STASSI
Yeah.
ROBERT
But I imagine by the end of June, yeah that video chat might be looking good.
LAURA STASSI
June? Oh, is it really gonna be that long? I think I need some more inspiration for getting
through this very trying time. I'll share with you something that's working right now. I have
on repeat the Van Morrison song Brand New Day. My favorite verse goes like this:
And my heart is still and I've got the will and I don't really feel so mean.
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 Patrick Fort mixed this
episode. WAMU's general manager is J.J. Yore and Andi McDaniel oversees everything
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