Season 1 Episode 11:
Transitioning Later In Life: Interview and stories by Pearl Bennett!


Phil: Hey,this is Phil aka Corinne.

Alex: And I’m Alex Berg. And you’re listening to…

Phil: The I’m From Driftwood Podcast.

Almost four years ago, our next guest Pearl sat down with I’m From Driftwood and opened up about her life and self-discovery

Pearl: In 1997, give or take a year or two. I was working out on Fire Island and I worked at this little restaurant called El Hot Spot. It was a Mexican restaurant. And I was told that I could wear anything I wanted. And in fact, they encouraged me to dress up. Be myself. I was wearing church dresses, sort of with hats. Sometimes all different kinds of wigs. And I didn’t know much about makeup, but I had some girlfriends that started to help me with the makeup and stuff.

I was given this creative freedom. I had basically lived as a gay man and Pearl hadn’t emerged yet. And so I was wearing – I just tried to put together things that I could find. A lot of the old drag queens out on the island would retire their drag and they would put it up at yard sales. And I would go shopping – that’s where I did my shopping in the beginning, because I dare not go to any store to buy women’s clothing.

And so I was getting ready to come into the city and I was going to go through my whole routine, back into my male clothing and get ready to come back. Simple. I’ve done it a thousand times. And at that time, I couldn’t get it together. I couldn’t change my clothes. And I couldn’t get out of my drag to go back into the city. And I felt so schizophrenia and I started talking to myself.

I said, “Okay now, Pearl. Come on off it.” Or I might’ve even talked to Ken.

I said, “Okay, chop, chop! Let’s get it together. Let’s get on that boat. Take off these clothes.”

And it was like, Pearl came out of me and said, “I’m not taking them off.”

It was like she – I said, “What?!”

She said, “I’m not taking this dress off.” And I’m holding a conversation with her!

I said, “Of course you are!” I said, “We can’t go…”

And so I went up to the Ice Palace and I remember talking to one of the… one of the entertainers there. I said, “I’m going back into the city justlike this.”

He said, “No, Pearl, you got to take it off because you could be beat up. Or you could be…”

I said, “Pearl won’t take – let me take the drag off!” I know they probably said, This child’s been doing a little too many drugs.

So I ran home, got my bag, got my stuff, and I got on the boat. It was the most surreal trip across the bay from Cherry Grove back to Sayville. And I’m on the way in and people are looking. And I looked just like what I am. And I go in and I remember walking through Penn station, and I’m in a flowing something. And people – and when I looked, like in my wake, you know how you walk past somebody, and if you look back real quick in your wake, there’s all these people staring like, What?! And I get on a subway and I catch the train on back down this way.

Now it’s getting ready to just throw away everything out that I thought I was. A gay black man living with HIV.

The big hurdle for me was telling my family about my living as a woman now, living as a transgender woman. What I did is I went to a friend’s art opening and they took this wonderful picture of me. And so I had that picture blown up or made into a photograph. I wrote in – a little note in the picture saying that my name is Pearl. This is… this is how I look. And I closed the thing, I packed, and I wrote addresses and I put stamps on it and I mailed it all.

Then I followed it up with a telephone call. I waited until I thought everybody had gotten the pictures. I call my mother first.

And I said, “Ma?”

She said, “Yes?”

I said, “Did you get my picture?”

And then she said, “Yeah…” She said, “What was this all about? Like, she…

I said, “Well, Ma, did you get it or not?” She’s beating around the bush. She would loved to have said, No, I didn’t get it, and maybe this would go away, but it’s not going away.

And she said, “I got it. What is wrong?”

And I said, “Nothing is wrong.” I said, “I wanted my family to know what’s going on with me. And include you in my life.” And I said, “I’m telling all of you.”

She said, well, “Don’t tell your oldest brother.”

I said, “Too late, Mama. I’ve sent him the same picture.”

“Well, how about your sister?”

“I sent her her a picture, too.”

“And I assume you sent Junior a picture?”

“Yes.” So that was that. That’s how I came out to them.

Didn’t hear anything after that. And then a few months later, this was about 2002, my bell rings. I go – I’m here with my lover, we’re in the bed. My love has no clothes on.

I go to the intercom and I said, “Who is it?”

And my nephew says, “It’s Todd.”

I said, “Todd?”

“And grandmother’s here with me.”

And she says, “Bernie opened the door!” And she’s looking at me and she’s this – you don’t know what to say. And I know she’s taken it all in.

And she said, “Well, Todd’s having a dinner party for us tonight.” And she said, “You’re expected to be there.”

I said, “Oh, you want me to come?” I said, “I’ll be there. I’ll be there.”

And I came in a – I dressed and I don’t know what possessed me to wear a blonde wig. I felt it. And when I came in, I found this a little endearing mother said, Oh, why didn’t you wear the other hair? I liked that. In a – in some kind of odd way, it was like, she liked that look.

So anyway, things were going well. My nephew cooked a beautiful dinner and we sat. I met a lot of the other relatives. Everybody was a little stiff and a little awkward because you know, I’m meeting them for the first time they realize I’m transgender.

My nephew is so happy to have my mother and me there, but he, I see he’s still a little nervous, but sweet, sweet man. After we ate dinner, I went into the living room and started talking with some of the people. I’m feeling more comfortable now.

And then all of a sudden, I hear this voice saying, “Bernie, what is all this?” And it sounded familiar. And when I spun around it’s – I see that look in my mother’s eyes of, like, back when I was a kid and she was, like, a little drunk.

And she looks at me and she said, “What is this?” And she strikes my breast.

And I said, “Mama, what are you doing?” And I realized that she’s drunk.

And she – that’s when she said, she came in close and she said, “I just want you to know that West Palm Beach is not big enough for Pearl and the Bennetts.”

So she’s getting a little drunker and I know she could be violent. So I got up and I said, “You know, it’s time… a gut feeling is telling me it’s time to leave. The party’s over.”

And I went into the kitchen and I thank my nephew and I said, “Todd, thank you. The dinner was wonderful.” I said, “Thank you for inviting me.” And I said, “I’m not going to be spending the night.” I walk out the door. And I don’t… I don’t say anything to my mother because I don’t want her, you know, I just want to get out of there as quietly as possible.

And when she heard the door close, she realized I had left the room or left the apartment. And she opens the door. She flings the door open.

She yells, “Bernie, get back here!” I don’t look back. And I walk to the elevator. It’s at the end of the hall. And I pressed the button, the down button. And she’s yelling and she’s screaming. And the doors open.

And she said, “Come back here now!” And I – doors close, and I can hear her still screaming. And down I go.

And she called the next morning and said, “Didn’t we have a great time?”

And I said, “Mama?”

She said, “Are you coming? We’re going to do something tonight?”

I said, “No, I’m not coming.” She couldn’t understand. And I realized then she was in a blackout that night. She didn’t remember anything.

When I left that apartment, I felt like I had been ostracized from my family and that I no longer had a childhood home to go to, go back to.

I no longer saw my mother in person while she was alive after that visit, even though we spoke on the phone almost every day. We made peace with each other. I forgave her. And. I knew I loved her. I was able to tell her that before she died. And at the funeral, it seemed like I had come… you know, I remembered that conversation we had had at my nephew’s house, that West Palm beach wasn’t big enough for Pearl and the Bennetts Here I stand in front of my child at home in West Palm Beach. The home of the Bennetts. Certainly there’s more than enough room.

Alex: Please. Welcome back to I’m From Driftwood, the one and only Pearl. Hi there.

Pearl: Hi!

Phil: Hey Pearl, how are you?

Pearl: I’m fine. I’m happy to be here. Glad to meet both you Alex, and you Phil.

Phil: Oh, so nice to have you here.

Pearl: Yes. Yes. Yes.

Alex: Well, we are so excited to be talking to you and honestly, we should just get right into it because there are so many questions that we have. It’s been almost four years since we spoke to you last. So we’d love if you could start with an update about how you’re doing now?

Pearl: I feel like I’ve grown a lot. Through a lot of experience. And what is that saying? You… when you know better, you do better.. An how I’m doing now, of course, I have to take in consideration of COVID-19, sheltering in place, I really haven’t seen a lot of my friends. I haven’t gone to a lot of my – any of my face-to-face support groups, but I have done a lot of stuff on Zoom.

You know, and I’m – I turned 70 years old while this is going on.  I thought I was going to have a birthday party or do something special for 70 being a big milestone.

Phil:I have a question for you. Alex and I are huge fans of your original stories. Do you have any noteworthy memories from your time of shooting with us?

Pearl: I was terrified when I did that interview with Nathan and Damien. All day in the apartment, we were here all day. They just let me talk. And I talked and I talked. All I know is when it starts – when those stories start pouring out of me, I just felt like, Wow. First I was scared because I was, you know, it’s always, when you’re telling your story, how is the family going to react? How are certain straight friends gonna react? You know, I was just letting it all hang out. And so a lot of people didn’t know a lot of that stuff.

So… and once I started telling the stories, it just felt like, wow, I just, I felt like I was just letting out so much stuff that I had been holding in, or stuff that I had told in bits and pieces. And so my… some of my relatives heard – they saw the videos. So, you know, and I talked with Nathan and Damien and that they were gonna keep the – these videos be here long after I was gone. And that if it could help one person – one person – it was worth it all those hours.

Alex: I think that that is such an amazing way of framing it and just seeing this – the power of storytelling and just how your own experiences can affirm someone else or help them see themselves reflected in your own story. And it sounds like it was almost a cathartic experience for you just being able to put it all out there.

Pearl: It was.

Alex: Yeah. And in particular, I love that in one of your stories, when you spoke about your time working at El Hot Spot, when the owners told you that you were able to wear what you want and they encouraged you to… to dress up and you literally started wearing dresses. Looking back on that, I mean, do you feel like that was the first time Pearl was coming to the surface?

Pearl: Yes. I would never wear the drag in the city. And in the story about, you know, when Pearl, she told – she turned and told me, “I’m not taking this dress off,” I had never been on the Long Island Railroad with a dress on. Walk through Penn station. They were terrifying experiences, but yet at the same time, they were so freeing and they felt so right.

And I saw the possibilities were just, ahhh. I went through a puberty, young adult and I aged into this woman, that sort of mature woman that Pearl is today, that she can sit and hold her own. And loving more who I am allows me to empathize and love my trans sisters and brothers and my gay brothers and sisters, look out and see even the people that… that don’t understand my community and even may want to do harm, I see the ignorance in that, where the fear – people fearing what they don’t understand.

Alex: You know, hearing your… the way that you described that moment, walking through Penn Station in the clothing that felt affirming to you, on this podcast, Phil and I have spoken about how we’ve both been affirmed in our identities by clothing. So that’s just something that really resonated with me in terms of what you were saying. Looking back, were there instances before then that you had thought about all of this?

Pearl: Back in the seventies, I remember that I went to a friend’s house in the Lower East Side. And the gay life was centered around Greenwich Village then before it moved up to Chelsea. And now, I guess it’s up in Hell’s Kitchen now, the epicenter of gay life. But I remembered that we were drinking and I think my friend helped dress me, but I put on a dress or gown or something and a wig. And I think this friend did my makeup. Now this was in the seventies, this was wild. This was 20-what… 27, 28 years before Pearl. She was always there. And I know she was there because this was an example of how I knew Pearl was always there.

I remember getting dressed and we got in a taxi and went down to the village and we went to a place called Peter rabbits. And that was a little gay – it was gay certain days. They had drag queens performing and they had this and that. And I remember very little of it ‘cause I had to be plastered to be in that dress ‘cause I did not have the nerves to be in that dress. And so all I know is I was dancing. I was told I had a good time. And I remember when I woke up in my friend’s house, I had the wig on still, I had the dress on still and I did want to take it off. And they said I was the life of the party with this party dress on.

I was kinda shy as Ken. Always quiet, Ken dressed very plain. Nice guy, but Pearl was just… she was out there. She was doing things. She was… she was just alive! Bigger than life!

Phil: It’s pretty clear that Pearl is undeniable. Can you tell us a story of how you came up with Pearl and how Pearl got her name?

Pearl: It was during gay pride weekend. I was invited out by my friends to Fire Island. I went out after the parade. I think it was 97, 98. That year, the theme for the gay pride parade had a Mardi Gras theme. And I remember they were throwing these beads out from the floats and stuff. And I ended up getting quite a few of the beads, and the beads I really liked were the ones that looked like pearls. And I took them to Fire Island with me.

I was going out for a week’s holiday and my friend Myron at the time was the chef at El Hot Spot. So I put my stuff in the house and I came down and he wanted to show me where he was the chef. They were so busy that evening.

And so I told him, I said, “Myron, instead of just showing me, let me help you!” And so I insisted so he said yes. And I came back, I put my pearls on and here I am. I’m helping him clean tables. I’m picking up food.

Some guy in the kitchen said, “You! Your food’s ready!” And I went, ran to get the food and this and that. And at one – some point in there, he said, “You! Pearl!” Because I had the pearls on. When he said “Pearl,” I looked and I… I thought about it and I said, Oh my God, I like that. And Pearl was a name for my generation… my grandmother, my aunts, my… this was a name that was popular then. We didn’t have the Afrocentric names back then. But I liked Pearl. I said, Oh, I like it. I literally kept that name from then on. And so I don’t think that guy to this day know he named me.

Phil: That’s such a great story. I love… I love how Pearl got named. It’s pretty incredible. You know, when you were coming out as Pearl, you sent your family a note as well as a picture. Did you hold on to the picture or the note?

Pearl: I have the picture and I have that picture that I sent to my family. I had to go through it and look for it. And when I found it, I made… I took a very good photograph of that picture and I was able to put it on my Facebook page. And that picture is of me around early 2001. I sent that picture – and I will forever hold on to that picture.

Alex: Well, staying on the topic of your family, in one of your I’m From Driftwood videos, you speak about being invited to a party by your nephew and a pretty tense situation with… with your mom, which led you to leave. How do you feel looking back on that now?

Pearl: Oh my God. From the woman… the one woman I wanted approval from and the love from I, you know, it was just very hurtful. But I knew I loved her and I’m so glad that I got the chance to make up with her and we got to speak before she passed away. Yeah. That’s a tough story for me.

Alex: That sounds, like, incredibly difficult to navigate. And I just have such an appreciation that you opened up to us to talk about that experience. I mean, it sounds like so much to take in and process in the moment and even all of these years later. Were you ever – you mentioned that you were able to eventually talk to your mom. I mean, did you ever confront her about her actions?

Pearl: I never did confront her. We went… for a period there, we weren’t… we didn’t speak for a while. And I think I was still in therapy at the time. And I think I even upped my therapy to two times a week. I just needed space and time to heal. And do I regret not confronting her with this?

Part of me would have loved to, but eventually she started getting sick. She never came back to New York. She wanted to, but I just loved her sort of from afar for a while. And then I was able to tell her on her deathbed that I loved her. Well, before that. I had talked – I started talking to her every day then. And I think I did it not only for her, but I did it for me as well.

And I’ve heard people handle these situations and in so many different ways, but I went on my gut feeling and what I could live with and what I… I didn’t find it any need to do that at that time – and her, especially as her life was ebbing.

Phil: That makes all the sense in the world. I completely understand with your family though, were there any members of your family that accepted your transition right off the bat?

Pearl: My brother back during the early 2000s was leaning toward Born Again Christian. He was a photographer. We were very close. That was hard for him. And my sister, she wasn’t having any of it. And I was very close to her ‘cause we spent the most time together ‘cause when my older two brothers left, we, my sister and I were in the house together. And I braided her hair. She got me all the Barbie dolls and I would tell her what I want so she could tell daddy. So when my parents went to work, I got to play with the Barbie dolls and the Easy Bake Oven.

Now, I think that we grew up in a time where that was just not acceptable. And I, you know, and my mother had gay friends. That’s what seems so strange. And my sister, she, one of her best friends was a gay guy that she loved. I knew him when I used to go hom. And he passed from AIDS, but that was one of my sister’s best friends. And he was a gay guy.

But now, my sister and I got along when I was just gay, but Pearl, no way. I got along with my mother when I was just Ken. And my brother got along with me long as I didn’t bring up any of this gay stuff. And remember my mother making a statement when I was still in school and living at home, I think I was in like the eighth, ninth grade. She said, “The one thing I would never permit or allow in my house is for anybody, any of you”  – well, she was directing it at me – “to put on a dress.”

And I think we were watching something on TV and it was some show. And I didn’t like to watch anything gay or even hinted of gay with my family because I was too afraid of how they were gonna react. And I like to watch those things by myself so I could get into them and feel the fantasy and this and that, but I don’t know what it was. It might’ve been Flip Wilson on TV doing Geraldine.

You know, to this day, I’m very supportive of my sister because she’s going through her own health problems now. But do you know to this day she will not call me Pearl? I’ve been living for 20 years before some of her grandchildren were born. She cannot – and she loves me! She loves me. But she can… she has a hard time with that. And now she is going through her own illness and stuff.

And I made up my mind, because when my mother passed away, I took – Pearl went down to Florida and I got – the whole family got to see me. And I went down for my mother’s funeral, but I felt… I asked some friends to go with me. I reached out for help and I had two of my best friends. One lived in Fort Lauderdale, and one was my best friend up here. And we flew down together to West Palm and… and they supported me through the wake, the funeral, the burial, and through going back to the house and I will forever be grateful because they reminded me of who I am.

Alex: Well, Pearl, one thing that I’ve noticed throughout this entire conversation is that you really built all these moments in your life to empower yourself, whether that was making sure you had these friends who were chosen family to come with you to the funeral, whether you sought to work through the issues that had been a result of your family for yourself so that you could self-actualize and so you could empower yourself. And something you also said earlier was that you have a sense of longevity. So I was wondering, is there any advice you would give to young trans folks on coming out to their family?

Pearl:I would advise if you’re going to do it in person, making sure that the environment is safe. I don’t know if they would like to do it like I did it, like, tell all of the members and that way the family would have each other to lean on when they’re… if they’re going through, you know, when they’re dealing with their feelings about their loved one. And another thing is if you need to have a friend support you, I would suggest that. And another thing is talk with somebody before you do this. I suggest that everybody should be in some kind of support group.

Alex: Well, Pearl, looking forward, what’s next for you?

Pearl: I take it one day at a time, so I don’t know. I’ve done a lot of stuff that I haven’t seen come out yet. I’ve done two photo shoots. And one was so professional and they had a car come and pick me up and take me to Brooklyn. And I went to this warehouse and they did a whole photo shoot up of me and I had the, like, hair, makeup, wardrobe. And the whole nine yards. Really felt like a professional shoot, and I had never done anything like that. And that could end up on billboards and posters and, who knows, on the side of a bus or anything.

And now this new, new something has emerged that was peaking out all the time. Pearl was there. She didn’t have a name, but she was there. Everything up to this point has led to me being true to myself as a transgender woman. And I, at that point, I had no idea what that meant because for the next 16 years, and it still continues today, it’s… It’s been a journey and I wouldn’t trade it for the world.

Phil: Pearl, it has been such a pleasure speaking with you today. What a wonderful conversation we’ve had today with you.

Pearl: Thank you.

Alex: Thank you so much, Pearl. It was truly delightful.

Pearl: Oh, you guys… you guys are the best. The best. And Andy! I know you’re somewhere there!

Phil: I’m From Driftwood Podcast is hosted by Phil aka Corinne…

Alex: And Alex Berg, and is produced by Anddy Egan-Thorpe.

Phil: The Podcast is recorded as part of I’m From Driftwood, a worldwide nonprofit LGBTQIA+ story archive, and is funded in part from TD Bank and Heritage of Pride New York.

Alex: I’m From Driftwood was created by Nathan Manske to help queer and trans people learn more about their community, help straight people learn more about their neighbors and help everyone learn more about themselves, all through the power of storytelling. The IFD program director is Damien Mittlefehldt. The stories you heard today are available in their entirety plus thousand more at…,

Phil: Please follow us on Instagram, Facebook, and YouTube. And our score is provided by Elevate Audio. Be sure to subscribe to our podcast wherever you get your podcasts.

Alex: Thanks, y’all for listening.

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