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Okay, here's the show.
As always, thanks for listening.
From the New York Times, I'm Anna Martin.
This is Modern Love.
Today, I'm talking to writer and therapist Gail Rice.
When Gail was about to turn 70, she realized what she really wanted for her 70th birthday was an orgasm.
So she decided to hire an escort.
And when I heard about this, I had approximately a million questions for Gail, which she was kind enough to answer for me in detail.
But look, knowing what she wanted was one thing.
Figuring out how to get it was another.
We talked all about it.
Stay with us.
All right, Gail.
Yes.
We are here to talk about an essay you publish in a sub stack called Oldster.
And the title of this essay is an amazing one.
This is the title.
For my 70th birthday, I hired an escort.
That is a splashy headline.
And I have to know just straight off the bat, where did that idea come from?
Well, the idea came from sort of an existential dread of turning 70 is where it came from.
It felt quite scary for me.
And I was really feeling frightened of sort of just fading away.
So I thought I needed something.
I thought I've got to do something really exciting for my birthday.
So I did a few things.
I planned a few trips and things.
And did that and then – but still didn't feel enough.
So I thought of jumping over a plane because I've often thought of doing that.
Hold on, hold on, hold on, hold on.
You can't say jumping out of a plane in that kind of toss-up.
You know, I planned a few trips and then I also jumped out of a plane.
And I actually want to go back even before we get into the plane of it all and say –
You're talking about a fear of turning 70.
Can you talk more about that?
Well, I think it was a sense of time running out.
I think it was really, I lead a very sort of full, happy life, but I felt I could feel it ending.
I guess that's what it was.
I think I was thinking, wow, 20 years ago, I was 50, 20 years going ahead, I'm 90.
And it scared me.
It scared me alive, really.
It felt like I needed something I was kind of scared of.
Because I was scared of turning 70.
I felt, in a way, I had to counter it by doing something I'm scared of to wake myself up.
It's hard to explain, but I needed a body jump.
But it could have happened jumping out of a plane.
Tell me what you mean by body jump.
Well, I needed to feel alive in my body.
Like, how can I get my heart jumping?
You needed a jolt.
The battery needed a jolt.
Yeah, my battery needed a jolt.
And if it was going to be alive and alert in the next 20 years, I needed to get it going now.
When you think of something to get your heart pumping.
Honestly, the first thing I think about is jumping out of a plane.
Absolutely.
But the escort does not track for me as much.
What were you fearful of with the escort?
I just think something happened when I started thinking about getting my body going that made me realize – I stopped dating apps at about 65.
Okay.
So I hadn't been dating and hadn't had any relationships since then, no connection with anyone.
And I think maybe something quite unconscious happened.
When I thought of being strapped to the guy in the parachute.
I think something happened that said oh –.
Maybe there's another way I can get connected to somebody.
And I just slipped into that.
Uh-huh.
You say you stopped dating apps at 65.
Why did you stop?
Well...
Because basically I was frustrated, disappointed, fed up with meeting men.
I got to a point where I said to a friend, I've got three things now I look for in men.
Can they walk around the block?
Can they do that?
Have they asked me anything about myself?
Yep.
Anything?
Yep.
Low bar, very low bar.
Listen, I have the same bar, but please continue, yes.
And the third one was, do they at least show some capacity to pay for the drink or the coffee?
I don't need them to pay for it.
Do they just show capacity?
Like, do they have a wallet?
Yeah.
So, yeah, it was a lot of work for little return.
I wasn't even sure why I was doing it anymore.
Yeah.
Gail, listen.
I cannot tell you how closely that tracks with my experience on the apps as someone in my early 30s.
So, you know, interpret that how you will.
You're a therapist, correct?
Yes.
I'm a therapist, and I hear that.
And that's the other reason I got out.
I know.
Whether you're 20, 30, or 40 women, this is what's happening.
Can I ask you too on that list of you know he should be able to walk, he should ask you questions, he should at least have the capacity to pay.
Was a fourth, like he can pleasure me.
He can give me an orgasm, or did you not even get that far?
Well, yeah, it wasn't even the orgasm.
I think it was...
Yeah, can he—well, first of all, they weren't very attractive, these men, because they're old.
And, you know, I look at myself.
I'm old, too.
But it sort of—no, it didn't even go that far, Anna.
It sort of—it was so—it felt so remote.
You're talking about the feeling of going on these dates, you felt very removed, right?
Sort of maybe not embodied on the—and so you stop— you know, engaging with the apps.
And then it makes sense to me that for this big birthday you're really thinking about something and your words sort of jolt you into your body, right?
To make things feel less remote, to make them feel immediate.
So I do understand how you arrived at Googling male escorts.
And now we got to talk about that.
How do you find an escort?
Do you just Google male escort near me?
Yes.
Yeah.
And what I realized very quickly was, you know, they all were the age of my grandchild.
And they were all the same kind of model of here's my bare chest, here's me with hardly, you know.
Hardly any underwear on.
Here's me sitting this way, that way.
Here's me as a sexual object.
And I thought, oh, no, I'm in the wrong pond.
So then I started looking for sexual escorts that cost over.
So I started to realize, looked at the cost.
So it became the higher up I got.
The less pecs I got, the less bums I got, and what I got was, you know, people that looked like they had a life, and then it also were a few more people that were in their 40s.
So it worked for me because I got a slightly older group and I got people with their clothes on.
So when I finally honed in, there weren't many.
There were a couple.
And I really quickly... honed into Mitch because a couple things.
First of all, his photos, but then he also had a video of him speaking.
Oh.
Yeah.
And just talking about how women like men have needs that aren't met in normal relationships.
And it was a very kind of psychologically reassuring chat he was having.
Yeah.
And this person, Mitch, the names in the story have been changed, by the way.
Mitch was the escort who you kind of finally zeroed in on, right?
That's right.
So I felt really reassured, and I told him...
I was anxious about being 70.
I told him I wanted an orgasm.
I told him I wanted an erotic massage.
He said, absolutely, no problem, easy peasy.
Wait, Gail, you told him that you were nervous to turn 70?
That feels pretty emotionally intimate.
I don't know.
Well, he was very – but he was very much like that.
He was –
You know, I said to him you'd make a good psychologist because he had a way about him that was very warm and he seems to be a man with a lot of integrity and he really wanted this.
He heard me.
He said, I understand that, and you're being very clear, and I appreciate that, so it should be...
No problem.
How much was it?
Well, it was $550 an hour, and you had to get three hours.
Oh, wow.
Okay.
So this was on the higher end, certainly.
Yes.
Well, as I find out, there's higher.
But, yeah, this was higher end and extravagant because, like, for me—
I'd rather, you know, I'd rather get a plane ticket for that.
I mean, it was a lot of money.
So, yeah, so it was a big investment.
And again, I don't know.
See, I think I was in such a space with this 70 thing.
It felt like, you know, my life depends on this battery jump.
And if this is what it's going to cost, this is what I do.
You paid the money to Mitch.
Yep.
And then?
The night comes.
Yes.
How were you feeling?
Look, I was really nervous going in.
It was the evening of my birthday.
So the next day is my birthday.
So I was going to be waking up in the hotel on my birthday.
Oh, my gosh.
Great planning.
Okay.
Copy that.
Okay.
So, yeah, I was very nervous.
You've never done anything like this before, right?
No, I don't know anybody who's done it.
I don't know what I'm doing.
And I guess the other thing, I was a bit shocked because I had this image of –
Oh, you know, I've got the champagne on the ice and I've got this lovely bedroom and he's going to knock at the door and come in and no, you have to meet them in the lobby.
So I thought, oh, so that's pretty not sexy.
So I go into the lobby and he looks exactly like what he did in the picture and- Feel.
But it just feels so weird.
He comes over and I think he kissed me on the cheek or something and And that journey up the elevator just felt like what am I doing in this elevator with this stranger?
And we are talking about the weather.
And it's so, so I'd lost any sense that it had in the hotel room with the champagne and the view.
So then it was like this very uncomfortable entry in.
Okay, so you're in the elevator with Mitch, meeting him for the first time, talking about the weather.
Tell me what happens next.
So then we get to the door and I mean I guess I'm so grateful for the champagne because I sort of knew I had that to lean into.
Then what happens, and this is where it went off the rails.
So I go into my room uber interviewing mode.
Huh um oh, tell me about yourself.
I heard all about his marketing job and how he quit marketing because he saw this was a niche market and he liked having sex.
And then I heard all about you know what it's like to be an escort, and so asking him about the kind of women that came to see him, and you're basically treating him like a client for therapy.
Well, almost worse than that, it felt like I was interviewing him for the you know the paper It felt like – and he was enjoying it.
Look, he's a really nice guy, interesting guy, and he was saying –
So I asked the kind of women who come to see him and he says well, they normally go into two groups.
So there's the women in about their 30s that are just looking for hot sex, and then there's the women, probably over 50s, who have been divorced, their husband died and they're looking for a boyfriend experience.
And I said at that point, I said, well, I don't really fit into those categories.
Yeah.
You're looking for an orgasm.
Yeah, I'm looking for an orgasm.
And he said, oh, yes, yes, I know that.
So I don't know.
We kept talking.
And then I – and there was this big clock.
There's this huge tower clock outside the window.
And I looked up and I was shocked.
Like nearly an hour had gone by.
Yeah, one of three.
I looked up, and what I felt was, fuck, I've just spent $550 interviewing this guy.
And I felt kind of a bit of rage, so I said to him, well, what do we do now?
And by the way, Anna, there was no physical touch, nothing.
I was going to ask.
No, nothing.
Not a touch on my knee or nothing.
He sat over there.
I sat over there on these chairs, and I interviewed him.
So then he says, okay, well, I guess maybe let's stand up.
And he said, maybe a kiss.
I thought, oh, it didn't feel right.
But anyways, he did that.
We stood up, and he gave me this really awful, slobbery kiss.
It felt way too intimate.
Right, yeah.
Out of nowhere.
Yeah.
No windup.
No windup at all.
Yeah, it just went from there.
It went from bad to worse.
We'll be right back.
All right, Gail.
So Mitch has just given you kind of an awful kiss.
Keep going.
Tell me what happened next.
Then it just sort of, we just sort of got out of our clothes.
Sure.
I took my clothes off.
He took his clothes off.
So I left my underwear on.
He left his underwear on, put them on the chairs and sort of get in the bed in this very clumsy way.
There's a bit of me that felt like well, i don't know how this goes.
You know, i was still hopeful, thinking this is going to get better, and then i said to him, i said i think maybe what, why don't we do the erotic massage?
Okay, so he, okay.
So oh, my goodness.
Um, I've had massages all my life really, and this was like not even a good massage.
There's no way it was erotic.
It was like someone was patting my tummy and my arms with a bit of oil and then occasionally touched my leg.
That was the extent of the massage, the top of my leg, my arms, and my tummy.
Wow.
And that was it.
And I just— That does not sound erotic.
You're right.
That sounds like a pat down.
A pat down.
And I'm not even sure what it was.
So I—and he just kept kind of stroking me in a weird way.
I never got my underwear off the whole time.
And did you want to?
It doesn't sound like you really wanted to.
Well, no, I don't know what I want.
I wanted someone to take charge.
Can I ask, like, when he was, you say you've gotten massages your whole life.
Was there ever a moment where you were like, Maybe I should give him feedback.
Maybe I should say that I... Like, did you say, I'm not enjoying this?
No.
Did you vocalize that?
What I'd hoped was he would be taking charge, which is something I don't give lightly to people, and I certainly don't give it lightly to men.
I mean, this is what's so complex about this.
I think what I realize with this is...
I wanted someone, for once in my life, to give me pleasure without me having to.
I might have paid for it, but without me having to pay for it in all the ways I've had to pay for it, if that makes sense.
What do you mean by that?
Well, I mean to pleasure them first, or to be the nice girl, or to, you know, be the person that's always concerned about how he feels.
I wanted to have a chance to have it all about me, which is I thought what I was buying.
But it felt like he had his head on my shoulder most of the time.
And it's like I was almost patting his head.
It's also kind of maternal.
It's very maternal.
Really awful.
And that's – sadly, a lot of my life has been looking after other people.
So this just not does – this does not turn me on at all.
And I –
I think I finally, I was finally able to say I sort of drifted off to sleep, I think because I was bored.
Or maybe just checking out.
And at one point I thought, oh gosh, I'm going to sleep.
And he said, oh, it must be because you're so relaxed.
I said, no, I don't feel relaxed.
Oh, he said, what, you don't feel relaxed?
I said, no, I, this isn't working.
Wow, so you did speak up eventually.
Finally, it took me a few hours, finally I said, this isn't working.
And he looked at me, up at me, because he's got his head on my shoulder, like a dog really.
He sort of looked at me with these big droopy eyes and said, I'm so sorry.
Wow.
And then I said, yeah, I am too.
And he said, you know, sometimes it's just not a connection.
And that woke me up.
That woke me up.
I said, no, I didn't ask for the boyfriend experience.
I asked for these things.
He said, yeah, but just sometimes there's no connection.
I said, well, that's really disappointing because I didn't understand that's what it was about.
I said, I think it's just best if you go.
And he looked devastated and he left.
And you know this is interesting because the hotel had delivered me a little piece of birthday cake and I didn't want to eat it before because I didn't want to be full or whatever.
So I got back in the bed with the birthday cake and the rest of the champagne and that's probably the best beer of the night.
But I was up all night just fussing about – and it's hard to explain what I was fussing about.
It was sort of like –
I guess there's a part of it going, oh gosh, I really am old.
It's really.
You know, I can't even get a paid worker to do their job because he can't connect with me.
You know, there's all that story.
Like there's a deficiency in me.
Absolutely.
Absolutely.
And then because I hadn't slept and it changed then.
It sort of changed into...
No, I'm mad.
I'm going to write him a letter.
So I was up at dawn and started writing this letter.
And dawn is your birthday.
It's your birthday.
That's my birthday.
Happy birthday.
That's my birthday.
But this is my birth.
This is the gift, really.
My voice.
I just got my voice.
I got her loud and clear.
Wow.
And so I wrote a letter.
And the letter was about we're both in the same business of servicing people's intimate needs.
You know, I do it as a psychologist.
You do it as a sex worker.
And our job, our job is to connect with what comes in the door.
We have to go with where people are.
I also said, I understand if you couldn't give me an orgasm.
That might not have happened.
But there was nothing that you did wrong that would lead any woman or person to get anywhere near that feeling.
It's interesting because, you know, the letter in some ways is extremely direct.
It's extremely direct.
And you are kind of calling him on the carpet in certain ways.
And you'd mentioned rage, which I think is a really interesting emotion to bring in at this time.
Yeah.
It was more a taste of rage.
It was more like, oh, my gut just felt furious.
You know, while I have not been in this exact situation, I will admit, this taste of rage...
I resonate with after an unsatisfying, intimate experience.
There's like, you know, to me, it's because I start to feel like it's my fault.
And then I get mad at myself for feeling that way.
And so the rage is perhaps like directed.
Inwards.
Not even so much at the other person.
Inwards, exactly.
Yeah.
Yeah.
And I think that's, I often say that to women, like anger, depression is anger directed inwards.
That sense of we get angry as women, but we often throw it back at ourselves.
Yeah.
And I had that experience.
And I could feel I wasn't going to stay there.
And that's what led me to writing the letter.
Yeah.
So the rage and the shame turned into something a lot more pragmatic.
Yeah.
I sent it to him and within like three minutes he'd text me back.
Absolutely, I'm giving you the whole refund.
And actually, I was shocked when he gave me a whole refund.
I thought if he just acknowledges this, it wasn't the money.
It was like, I need acknowledgement that this went really bad.
Yeah.
He wrote quite a nice email, and he said, look, I'm really sorry.
I know it didn't go well.
I can't really understand what happened.
I'm devastated.
I said last night it didn't go well.
I'm more than happy to give you the refund.
I'm more than happy to talk to you if you want to talk about it.
So when you sent that letter and got his response, you know, and he sent you back the money, right?
Did you feel vindicated?
Was it like, all right, well, so there.
Like, what was the emotion for you?
I felt sad.
I felt... I felt...
Because I really think Mitch is a really good guy and I really think he was devastated and I felt sad for both of us in a way that it turned out so badly and I felt vindicated and I felt relieved.
He was the guy I thought he was.
So I thought, good girl, you can read people.
And at that moment, I decided I had to put that money somewhere where I'd do it again.
Whoa.
I kind of knew at that moment, if I don't commit now, it's never going to happen again.
Oh, my.
So, Gail, you're like, all right, we got to hire another escort.
Yep.
You rock.
Yep.
And then it was the feedback from the article that got my little bit of rage happening again.
The article where you wrote about your experience with Mitch.
Yeah, because alongside heaps of support was a very small minority of people, mainly men.
I think.
Saying things like, what did you expect, the poor guy?
Look what he had to work with.
A post-menopausal woman, you've got to be kidding.
Get a dog.
My God, that's very unkind.
That kind of stuff.
Basically, it was about poor Mitch.
Yeah.
Poor guy.
So that is what fired me up.
I thought, hmm.
It's like you're fired up to hire another escort.
Do you?
How do you find, I mean there's even more pressure, I would say, on the second experience, because the first one was so disappointing.
How did you... Did you adjust your approach to the search at all the second time around?
No.
Well, no, the beauty of this, again, this is the cosmos delivering to me, really.
But the beauty of this is I had all this feedback from women, you know, offering me all kinds of advice about sex toys and suggesting maybe I try a woman, and suggesting all kinds of things.
And in that, one woman suggested she'd been to this escort six times and she was in her 60s.
So his name was Chris.
I thought, there you go.
There's the guy.
And I find him on, like, I look at his website.
And the really funny thing about this was on his site, he said, I guarantee satisfaction.
I don't take payment until after the fact.
Ooh.
But I think there was, as what you said, a lot harder the second time.
Yeah.
What do you mean harder the second time?
You were more nervous.
Yeah.
Maybe it was me.
Ah.
Maybe it was me that's defective.
Maybe this will just prove that.
Maybe I do need to fade away.
You know, this was all a bit of a fantasy about this 70 battery jump.
So bring me into that.
Did you go back to the same hotel?
No, I chose another better hotel.
Oh, wow.
I went up.
I upgraded myself.
I thought, well, I'm at least going to enjoy the hotel experience.
Now I went to another hotel and it was sort of like this was less stressful because I knew the drill.
I knew I just need to get up on the elevator.
We can do this.
And then the bit getting into the champagne and the chairs, I know how to do that.
But what I made a vow to myself was Before I went.
I did quite a bit of work internally on myself and with my therapist too, on how I was going to approach this.
So I said to him, I'd done this once before.
It went very badly.
So I'm just warning you, I'm probably quite nervous.
So I said that.
But the key difference for me was I did not interview him.
I just let him take charge even with the conversation.
I said, you're a girl, Chris.
You tell me what we do now.
Yeah.
Was that hard to do, to hand over control?
No, because this time I decided that was the only way I could do it.
I realized I had to trust.
I had to trust that he could do the job.
Yeah.
And I actually, it was a relief.
It was a relief.
Yeah.
I mean, it's interesting because, again, there was nothing really sexy about the first bit.
You know you have this image of you've got the new sexy underwear and stuff and it's all going to be like this lovely seductive dance.
Not that.
It felt like Again, we take off our clothes.
You put them on the chair.
But this time he says, I think it's best to start with the erotic massage.
So he takes charge and does that.
And he can give a massage.
And it was a good massage.
I wouldn't say I'm still looking for the erotic massage, I imagine.
That's the third escort.
Yeah, yeah.
Mm-hmm.
The third one.
But it was good.
It was very good, very attentive, very good.
And I was present.
So by the time that was over, I was in a totally different state.
And then it just flowed.
I mean, one thing I did say to him at the start is don't kiss me, because that last kiss thing, I think, was really what set me off.
Too intimate.
But in the end...
In the end I asked him to kiss me, and that was actually one of the best parts of the session was the kissing bit, because I felt that solid and safe.
I showed up by asking for what I wanted.
And I wanted the very thing I told him I didn't think I wanted.
Which was the kiss.
The kiss.
So, and long story short, I got two orgasms.
Wow.
Yeah.
Yes.
Yeah.
And it came, it just came, literally, it just was so natural.
And yeah, it just felt totally opposite.
What a relief.
Yeah, in many ways.
And When he said the time's up, it just felt like end of transaction, crisp and clean and uncomplicated.
When you close the door, are you proud of yourself?
I'm proud of you hearing this story.
I'm like, fuck yeah, sorry.
But I'm like, okay, yeah, you gave up control when you wanted to.
You asked for what you wanted when you wanted to.
And you came twice.
Hello, this is awesome.
Hello, I got what I wanted.
And I felt very proud of myself and I felt very I mean, I just felt like something was completed and I got the jump.
That was what I thought I wanted and I was right.
And I came out of that feeling like I am a sensual sexual person at 70.
It's still in me.
I don't necessarily need to use it all the time, but I know it's in me and that gives me energy.
And this isn't the end.
No.
This isn't the end.
And I can ask for what I want.
And I'll find different ways to do that.
And I think that's the exciting bit for me, what I'm so proud of.
Because I was always someone who was determined I was never going to be in a relationship.
I knew at 17 I wouldn't marry.
I wouldn't have children.
No way was I getting trapped in a relationship.
Mm-hmm.
Because I grew up with a lot of responsibilities.
So I'd spent my life having to hold back a lot because I sort of was always one foot out the door.
So maybe this was, looking back now, I think this is the battery jump I needed to be present.
What's on the other side of that?
Well, another erotic massage.
I'm on the look for that.
Girl, I love that.
You were like, listen, I want what I want, and I've received an okay massage from Chris.
It did the job, but I want a truly erotic massage.
Yeah, I'm still on the look because I still realize I've got to look after that central part of my body.
I guess that's something I've learned.
So on the other side of it is, You know, don't get the cobwebs.
Don't let the cobwebs build up again.
Find a way.
And maybe next year is jumping off a plane.
There's something with my body.
You know, we opened up this conversation and you said that your 70th birthday, approaching your 70th birthday, made you think.
You know, 20 years ago I was 50.
In 20 years I'll be 90.
And that scared you.
You were scared of dying.
No, not dying.
I'm not scared of dying.
I'm scared of not using the time I've got.
That's it more.
I want to die knowing that I did everything I could do to keep myself alive and alert in the time I've got.
And part of that is me letting go of the things that held me back.
So all the protective defenses I had that held me back, like disconnecting from relationships and being in control and not allowing myself to be vulnerable and pleasing others, all those things.
I don't want them in the next 20 years.
I mean, I still feel time's running out.
It is.
But it's no longer as scary to you.
Is that true?
No, it's not.
No, that's right.
It's no longer scary.
And it feels like I looked after people for so long in my life that that was my main gig.
And this is about me now.
Well, can I ask you, like, Are you going to see Chris regularly?
Like, is this a quarterly business transaction or, you know, like yearly or something?
Well, no.
I've decided I'll never see Chris again.
Okay.
Because if I'm going to do it again, it has to be new and exciting.
Ooh!
It's more of the same.
I don't want to do routine anymore.
I don't want to, you know.
Yeah.
So it's somebody new.
And I'm thinking maybe, I don't know, maybe next birthday, something.
But it's got to be somebody new, a new hotel, a new person, a new jump.
When's your birthday, Gail?
April.
It gives you time to find the right person.
Maybe a woman?
No?
I don't know.
Who knows?
Well, and that's the other thing, because I am looking for a woman for the erotic massage.
Yeah.
Yeah.
I'm very clear on that.
Gail, I have no doubt and I really mean this sincerely you are going to get the erotic massage of your dreams.
I just believe that with my whole heart, and I just really do.
Oh, I love that.
Thank you so much.
We all can do that.
We all can get that.
If you want to read the essay that inspired this conversation, we'll have the link in our show notes.
And before you go, I wanted to let you know that the Modern Love column is looking for breakup lines.
Like when you were breaking up with someone, what did you say?
Or when someone was breaking up with you, which by the way, how dare they?
What did they say?
We're looking for lines that are surprising, shocking, maybe funny or poignant.
We're looking for words that have stuck with you.
If you want to share your story, there's a form you can fill out and we'll put that link in our show notes as well.
The deadline to submit is Sunday, October 5th.
The Modern Love team is Amy Pearl, Christina Josa Davis Land, Elisa Gutierrez, Emily Lang, Jen Poyant, Lynn Levy, Reva Goldberg and Sarah Curtis.
This episode was produced by Amy Pearl.
It was edited by Lynn Levy.
Original music in this episode by Marion Lozano and Dan Powell.
Dan also composed our theme music.
Our mix engineer was Sophia Landman, with studio support from Maddie Macielo and Nick Pittman.
The Modern Love column is edited by Daniel Jones.
Mia Lee is the editor of Modern Love Projects.
If you'd like to submit an essay or a tiny love story to the New York Times, we have the instructions in our show notes.
I'm Anna Martin.
Thanks for listening.
