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From Sherwood Forest to the Norman Court, a classic tale reborn for today.
The story continues to unfold.
When I was about 16, I was in love with a boy named Brad.
If you went to my high school in Maryland and are wondering, Meredith, do you mean that Brad?
The answer is yes, I do mean that Brad.
And yes, I've Googled him lately.
And yes, I know he lives in Connecticut.
Anyway, Brad was sweet and kind. and smart, with orangey blonde hair.
He made rhubarb pie.
He played the trumpet.
I loved Brad.
Deeply, spiritually.
I'm serious about this.
I think he was actually my first real love.
And Brad, he liked me a lot.
As a platonic friend.
I sort of knew this crush I'd been harboring on Brad was one-sided.
But on a random summer evening, I did something dramatic.
I thought, I'm going to tell him.
I was leaving his house after a night of hanging out with friends.
These friends hopped into her car and were about to drive me home.
But I turned back around.
I went right back into Brad's house.
He was still in his living room alone, cleaning up after the get-together.
And I said, from what I remember, something like, Brad, I think I'm in love with you.
I remember Brad just standing there, frozen.
He would have been about 18.
And he was like, okay.
Then he just stared at me with a face that said, can we please end this conversation, please?
It was not the result I wanted.
After that night, Brad and I continued to be just friends.
And the memory of the speech was a bit humiliating.
But I had no regrets.
There was something about the act of stating my feelings like a character in a movie.
Would that felt empowering important, even if my feelings weren't reciprocated?
It would not be the last dramatic speech I would make.
Between the age of 16 and oh, let's say 32.
I made a bunch of proclamations, most of which were received with a shrug.
I was most likely to make these speeches when the recipient didn't even deserve my attention.
And that's what today's new episode is all about.
The big speeches, the proclamations, why we give them, whether we should give them and what we get out of saying a dramatic thing, sometimes to someone who isn't even listening.
And here's where I'll dramatically say from the Boston Globe I want you to know this is Love Letters.
I'm Meredith Goldstein, thrilled to be back with new episodes and excited to welcome a really cool guest and delightful person.
My name's Jeff Hiller.
And how would I introduce myself at a party?
I guess I'd say I'm a middle-aged homosexual.
I'm an actor and a comedian and, you know, old, old and gay.
For those who don't know, Jeff was one of the stars of the HBO show Somebody Somewhere, for which he is nominated for an Emmy.
And the ceremony is next week, and he's up against Harrison Ford.
Jeff was tremendous on Somebody Somewhere as a character named Joel.
If you just give me like 15 minutes, I was thinking maybe we could go fuck up some donuts.
Oh, let's fuck up some donuts.
Let's fuck up some donuts?
They already got one hole in them.
Let's make it some more.
What has happened to you?
Over the summer, I read Jeff's new essay collection slash memoir, Actress of a Certain Age.
It is a very funny book about Jeff's upbringing, his experiences as a performer in New York and, most importantly, how one can have a big break even if they're middle-aged.
A lot of the book is about Jeff's professional journey, but there are some stories about relationships, about Jeff's marriage of many years, about his dating experiences or lack thereof.
Really, that part is why I wanted to have Jeff on the show.
He tells a story in the book that feels universal, despite its extreme specificity.
Picture this.
It's the early 2000s.
Jeff, who is from Texas, is in his 20s.
He's a young performer trying to make it in the big city.
He does improv, he has a day job, and he's working to make his art his life.
Socially, he is making friends and finding community, but he's not doing much dating.
I was disappointed by that and kind of like embarrassed by that and mad at myself for not having, I don't know, done more slutty things or something and had more relationships and lovers lovers.
What am I?
You know, I'm not French, so it's hard.
Ironically, at the time, Jeff is rehearsing for a production he's been cast in called Slut.
We were an off-Broadway show about young men.
20-somethings falling in love.
And I played a sea captain, a pirate.
It's during rehearsals for the show that Jeff meets a lot of new people who are in the same place in life.
We were all young and trying to start out.
And this was a huge deal in our professional lives.
And because we were all having that moment at the same time, we really bonded and got close and became friends.
And The lead actor was very handsome.
Jeff is going to call this handsome actor Freddy.
So Jeff and Freddy are in a cast of young people doing young people fun things.
So it should be no surprise that at some point another guy in the show I'm going to call him Bob approaches Freddy and says Hey, do you want to have a threesome with me and my boyfriend?
Freddy tells Bob, Yeah, I do.
It's in the lead up to this threesome that Freddie decides, with Bob's consent, that this should be a foursome.
Freddie approaches Jeff, our Jeff, and encourages him to join the festivities.
He said, hey, do you want to make it a foursome?
And this was crazy.
I was like going from zero to a hundred.
I barely had had any twosomes.
So to all of a sudden have a foursome was, you know, a above my pay grade?
But I wasn't going to say no, you know.
Everybody heads back to Bob's place in Queens for the foursome.
But before the action can actually begin, Bob and his boyfriend start arguing about whether they want to go through with this idea.
I kind of got the vibe that my presence was the issue that he had agreed to a threesome but not a foursome.
And, you know, fair.
Jeff and Freddie are awkwardly waiting this out.
Like, do we stay?
Do we go?
Freddie and I were sort of we were literally hiding underneath a blanket, just trying to not be present.
And finally, the fight had lasted so long that we just crawled out of the apartment.
And then we didn't have anywhere to go.
He lived deeper in Queens and I lived in the East Village at the time.
And so we just parted ways.
And I don't even think I kissed anybody that night.
After this evening, everybody goes back to rehearsals.
And weirdly, Bob doesn't ever bring up the almost foursome.
It's like it never happened, which turns into kind of a bonding thing for Jeff and Freddie.
Like, wow, that was weird.
The foursome that wasn't.
It's through this weirdness that Jeff and Freddie start connecting more with each other.
Then they start seeing each other.
We started dating, which means...
We would go to a bar.
He would get crazy drunk and then he would stay at my house in the East Village because it was in Manhattan and he lived in very far away Queens.
This doesn't sound very romantic, but it is a very 20-something relationship.
Sure, maybe Freddie is using Jeff for his apartment in a cool neighborhood.
But for Jeff, who doesn't have much dating experience at the time, it feels big and fun and important.
I had never even gone on a date.
I had had some.
You know I'm gay, so gay culture.
Just because you haven't had a date doesn't mean you haven't had a lot of sex.
I wouldn't say I had a lot of sex, especially compared to gay people.
I had had sort of anonymous hookups but I'd not really ever had a date, like even just like a date you know, like where you have dinner and talk to each other.
So have someone who i knew his first name and last name and i had been to his house and he had been to my house and we were, we had done this show together and it felt like we were doing art and everyone in the cast knew that we had sort of been hooking up and seeing each other and so it felt you know, all of the the women in the cast would come to me and be like, oh my god, you and freddie.
It felt like Like for the first time I had what I'd always wanted.
And so consequently, I mean, oh, Meredith, I fell in love with him.
I mean, I was in love with him.
I thought about him all the time.
I was talking about it with all of my friends. my pals and like my coworkers at my day job.
But there isn't a lot of consistency in the relationship.
Freddie is not the classiest when it comes to respect and decency.
They're not really defining what's going on.
And Freddie does whatever Freddie wants.
I kept a journal at this time.
I I've kept journals sporadically for the last 25 years.
So, and, um, And I usually tend to keep journals when I'm having some emotional turmoil.
So of course I was doing it during this.
And so I went back and realized, oh my gosh, this happened like three or maybe even four times where he would completely ghost me, would not call me or speak to me for a period of time.
And then would show up and confess that he had been having an affair with someone else, usually an ex-boyfriend or something.
And I would say, oh, that's okay.
Because we hadn't made any sort of decisions about monogamy or anything like that.
And so I was like, oh, okay.
It seems like it's bound to fall apart, mostly because the show ends.
So there's no built-in way for Freddie and Jeff to see each other.
But then, as if he has seen the light, Freddie offers more.
One night he showed up and he said he was so sorry for everything and he wanted this to be a real relationship.
He wanted to be monogamous.
He wanted to be my boyfriend.
And I was thrilled.
I was thrilled.
That night, they decide they should celebrate their couplehood.
Jeff says, maybe we should go to Dojo, this New York restaurant they both enjoy.
It would be a nice couple-y thing to do.
He said, no, I don't want to go to Dojo.
I want to go out.
I want to go out, out.
The only thing Jeff can think of for going out is that a co-worker at his day job is having a birthday party.
Freddie says, yeah, let's do that.
It didn't really feel like the appropriate way to celebrate becoming a couple to go to a party with other people.
But what do I know?
This is my first relationship.
The party is in a cool New York apartment.
It's a bustling social situation.
When they get there, Jeff starts to circulate.
Meanwhile, Freddie goes off to the bathroom, and disappears.
Maybe he's doing drugs, Jeff thinks.
Which is not ideal, but interesting that Jeff is already thinking I hope it's drugs, as if that's the best case scenario when it comes to Freddie.
Jeff, meanwhile, he's feeling magnetic.
Life of the party.
I mean, he's kind of riding the high of Freddie wanting to be his boyfriend.
And then I was talking to these women and even though I was like a little nervous about the fact that he wasn't around, but I
Was kind of on fire.
I was like really like sparking.
And these women were like really into me and laughing really hard.
But eventually Jeff is like, truly, where is Freddie?
I said something around like, I'm just looking for my boyfriend.
And they're like, oh, you mean that guy you came in with?
And I said, yeah.
And they were like, he's in bed with the birthday boy.
I turned around and all I could see was their feet.
If you can imagine it.
It's a New York City apartment that's small, but maximizes space with like a loft.
It's arranged so that you can kind of see everything, including the bed.
I was like sitting on these little chairs and the desk section underneath the bed.
And then when I came out, that's when I could see his little red converse sticking out.
And it was just like their feet told a story.
And the story was that there was no monogamy happening that night.
I want to take a moment to acknowledge the whiplash of the evening.
Jeff was just getting used to the idea that Freddie had shown up offering monogamy and couplehood.
And now only hours later, Freddie is in bed with someone else.
In this moment, Jeff gathers his emotional strength and approaches the bed.
He says to Freddie, I want to leave.
And he said, I'm not ready to leave.
And so then I left.
And then I walked home.
I thought, well, he'll call me for sure.
He did not call.
Days pass.
Like that cannot be a fun few days.
It was awful.
It was like three and a half days.
Yeah.
And I was trying to be cool.
That's why I wasn't calling.
I wanted to show myself as this like cosmopolitan person who was just totally fine with it all.
And I finally called him.
Because we had tickets to see one of our former castmates cabaret shows.
And he was sort of was like, how'd you get my number?
It was kind of like he just put on this whole thing of like, why are you calling me?
Just pretended like nothing had ever happened between us.
And I felt so embarrassed that happened.
It's on this call.
As Freddie is being an absolute shit, that Jeff does a thing that is so relatable to me, a longtime giver of speeches
Jeff makes a declaration of his feelings.
What does he say?
How was it received?
More when we come back.
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It's the early 2000s.
Young Jeff Hiller, inexperienced in dating, has been sort of dating fellow actor Freddie.
In the span of one night, Freddie goes from suggesting a monogamous relationship to hooking up with a random guy in front of Jeff.
In the aftermath, Jeff has gotten Freddie on the phone and Freddie is basically behaving like they never dated at all.
Faced with this rejection and disrespect, Jeff makes a declaration.
I just said to him I just want you to know you were the first person I ever loved and I will never forget you.
So beautiful.
So poetic.
What was Freddie's response?
Did he say, Jeff, you mean the world to me, but I wasn't ready.
Or Jeff, you deserve so much better and I wish you all the best.
No, he does not.
He said nothing.
Okay, drama queen.
And I mean, fair.
I mean, he's not wrong, but it was not the response I wanted.
Even if we were going to continue breaking up.
I was hoping he would take that gesture a little more kindly.
During this time, Jeff does not feel good about himself or about love in general.
I listened to Rufus Wainwright's Poses album just over and over and over again on a Discman.
That gives you an idea of what time of our lives this was.
And to this day, I can't even hear Rufus Wainwright sing at all, which is terrible.
He's a wonderful, wonderful performer.
But just his voice, which is so iconic and distinct, takes me back to that time immediately.
And it's such a depressing time.
Jeff says that as all of this is happening, Freddie starts performing in this musical review.
I didn't put this in the book, but I'll tell you and your beautiful listeners that I knew that he was doing a concert on 14th Street.
Jeff is even secretly hoping he might run into Freddie.
And I purposely walked down 14th Street every night, hoping I would run into him.
I didn't.
I didn't run into him, but I did walk down 14th Street every night.
In the moment Jeff doesn't feel great about the fact that he admitted his big feelings on the phone in such a big way.
Somehow, saying it to him, I actually felt like I lost a little power.
But was there actually dignity lost?
Who was Jeff's declaration of love really for, anyway?
I make a case to Jeff that none of us should have regrets about making big speeches, even if it is cringey later.
I will present my evidence board to him and to you.
Jeff uses the word humiliating when talking about all of this.
And sure, it does sound humiliating.
But I come from the school of not giving a shit about dignity.
Because you know who makes big speeches?
Main characters in movies.
I know that movies lie to us about what big speeches can do.
Films tell us that if we dramatically state our intentions, it works out beautifully most of the time.
I'm quite sure my speech to Brad back in the day was probably modeled after the speech Harry gives to Sally at the end of When Harry Met Sally.
And it's not because it's New Year's Eve.
I came here tonight because when you realize you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible.
That's an amazing speech that somehow also involves a lot of backhanded compliments.
Julia Roberts has made a career delivering speeches to men who stand there and stare at her and just kind of shrug.
In Notting Hill, for instance, she makes an epic speech to a guy who rejects her, at least in the moment.
I'm also just a girl, standing in front of a boy, asking him to love her.
Her best speech, in my humble opinion, is in My Best Friend's Wedding.
It's so heartfelt that it feels like she wins, no matter what.
Choose me.
Marry me.
Let me make you happy.
I won't spoil the end of My Best Friend's Wedding for those who haven't seen it, but the movie ends the way I want it to, despite the good speech.
The point is, if Julia Roberts can make a begging speech, look cool.
That means it is cool because she is speaking her truth, behaving like the vulnerable main character we're all rooting for.
By the way, talking about this reminds me of my best friend who, when she was in her 20s, called a guy who absolutely was kind of ghosting her and yelled don't ever call me again.
And he was like, okay, you literally called me.
That was main character behavior, even if it was embarrassing.
That brings me to my second point.
In Jeff's story, and in many stories, saying the big thing gives a person some semblance of closure.
If Jeff hadn't made his declaration of important feelings and Freddie hadn't been cruel by calling him a drama queen, Jeff could have held out hope that Freddie was going to show up later.
It's like when I made my speech to Brad by telling him I love you and hearing crickets.
I got my answer, which was no.
Another point.
It makes perfect sense that Jeff ended this relationship with a beautiful speech about the meaning of the experience, because a lot of the relationship was written by him anyway.
Jeff makes an incredible point in his book about how a lot of his connection with Freddie was invented by his own imagination.
In retrospect, Freddie was giving Jeff little to nothing, which meant that Jeff was filling in all these holes with his own creative narrative about how great the relationship could be.
This I relate to hard.
I remember telling 1X in one of my speeches we could have been amazing, but in real life we weren't.
I have talked about this concept with literally every single one of my close female friends, be they lesbian or straight or trans.
Everyone I know who identifies as female has had this issue.
And I know that the binary means nothing, but whatever.
This is my experience.
Someone isn't giving you a lot of information about what they're thinking about and what they're feeling.
You tend to create that information and unfortunately i should just speak for myself.
My imagination tends to be more generous than usually the partner actually is and i believe that they are curious and and interesting and because they're so quiet, i think like oh, they're so deep and profound and they have these interesting thoughts that they're shy and they can't figure out how to talk to me.
And the truth is, usually they're just quiet because they don't like to talk much and they are not having the feelings that I am believing that they are having.
And so when, yeah, the relationship goes south and they're like, what?
I wouldn't even into this that much, because I've created this whole, as you said, three novel arc for our relationship.
It makes it even harder to get over and to, um, and to just heal from that.
Something Jeff realizes, that I realize with him is that declarations and speeches can be more likely to happen when someone isn't being treated right.
Back to movies.
If Harry hadn't been awful to Sally after having sex with her and when Harry met Sally, he wouldn't have had to make that big New Year's speech.
And in Jeff's case, the way he writes in the book about his actual wonderful husband and talks about their relationship.
It sounds wonderful good.
So good that there's no reason to run around giving groveling speeches.
The intimacy becomes so much less grand.
It's less like sweeping and poetic.
And it's more like, hey, this is important to me.
Can we work on this together?
It's less like, I want you to know you've been so important to me like that.
I don't ever make that speech, even though he has been one of the most important people in my entire life.
Overall, Jeff is not as pro-speech as I am.
He says it might not always be the best thing for people to do.
Jeff actually told me he wished he'd written the speech down as opposed to saying it.
Regardless, he does know that the sharing of his feelings so many years ago got him somewhere new.
I did want him to know that he was special to me.
And even now, when I don't have the dumb goggles of love clouding my vision, and I can see that he was not special at all.
But in a certain way I'm glad that I got to say it.
I just wish he had been a little bit more tender in his response.
Which, by the way, his lack of tenderness in response just shows how not a good match we were.
I can't be with somebody like that.
I would turn to dust.
Now, this is my last thought on all of this.
I never thought of myself as someone who would receive this kind of speech.
But once, I got one.
I think I didn't realize it until years later.
A guy I knew, an acquaintance, emailed and was like hi, I know we only casually know each other, but I think we're meant to be.
And then he listed a bunch of reasons why.
It was not creepy, by the way, just really earnest and flattering.
But it didn't feel true or based in my reality at the time.
I remember telling him something like, actually, I'm not as great as you think I am.
And I'm not interested in dating right now.
And I wouldn't be able to be that great to you.
This nice man had invented all of this potential, but I couldn't even conceive of being the person he wanted.
He'd basically just written fan fiction about what it could be like if we were a couple.
Kind of like how Jeff had made Freddie more important than he deserved to be.
Looking back, I hope I was really kind to that man who liked me.
Because coming full circle, when I think about it, Brad was really nice to me.
He was 18 and he didn't know how to absorb my 16-year-old feelings.
And he was going to college and he just didn't want to date me.
And from my memory, Brad eventually smiled and made me feel less ridiculous.
I'm fairly sure that after I told him I loved him, he offered to drive me home.
Our friendship was real.
There was care and respect.
I will be forever grateful that he did not say, drama queen.
The point is, if you ever hear a speech like this, One of love and adoration.
And it comes from an empathetic person who cares about you.
Maybe be as nice as you can.
Because it took a lot to say it.
I want to say, in these new episodes of Love Letters, there's not one big theme.
But in recording a random assortment of stories, I have noticed that in each of them there's a moment of clarity.
In Jeff's case, one moment of clarity was seeing Freddie's feet in bed with another guy.
But the real moment of clarity to me came after he gave that speech, realizing it was time to let go, that Freddie was never the guy and that Jeff deserved better.
Let's look for these moments in all of the stories.
I'm so excited to share them with you.
Jeff Hiller's book is hilarious and I think it makes a very good birthday present for people figuring out who they are as they get older.
The book is called Actress of a Certain Age.
The Emmys are next week.
I hope Jeff wins and makes the speech of his life.
Love Letters is a production of the Boston Globe.
Our producer is Christina Hanatu.
Our executive producer is Kristen Nelson.
Story, edit, mixing, and mastering by Jasmine Aguilera.
This episode was co-written by Jeffrey Kelly with production assistance by Anne Lee.
Sound design by Christina Hanatu.
Special thanks to Nancy Barnes and Linda Henry.
Our music is from APM.
Remember, Love Letters is also an advice column.
Send any questions about dating divorce marriage singlehood whatever, to loveletters at bostoncom.
Find our newsletter at boston.com slash Meredith.
And if you like the show, please leave us a review.
Especially if you have an ego, wouldn't you be like, oh my God, I used to hook up with that guy.
I'm totally buying this.
Seeing if I mentioned.
Oh God, I hope he doesn't.
I'm Meredith Goldstein.
Thanks for listening.
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