Episodes We Love: Do I Follow My Head Or My Heart?
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WBUR Podcasts, Boston. The universe has good news for the lost, lonely, and heart-sick. Sugar is here. The both of us. Speaking straight into your ears. I'm Cheryl Strayed. I'm Steve Almond. This is Dear Sugar Radio. Oh dear song, won't you please Share some little sweet days with me

Dear Sugars, I'm a 34-year-old woman who has never been married but has had a number of long-term relationships. All of my relationships have been safe, meaning the men were pretty conventional, stable, and came from good backgrounds. I also come from a very good background. I had an idyllic childhood with almost no big trauma to speak of. My parents are still married, and I see them often.

Recently, I unexpectedly met the most amazing man whom I immediately fell for. We share an incredibly deep heart and soul connection. We were immediately head over heels in love, trusted each other, and both feel as though we've known each other forever. But there's one thing, Sugars. He comes from a background full of trauma. His parents, now divorced, were highly functioning alcoholics who occasionally physically abused him and his siblings throughout his childhood.

He has done a fair number of drugs in the past to cope with his situations, and he lives a pretty unconventional artist's life. I'm totally confused. The man I fell in love with doesn't appear to have gone through such immense trauma. He's emotionally and physically healthy, a very conscious and active participant in life, has a lot going on creatively, and is so full of love and emotion. He also seems totally resilient to what has happened in his past.

Despite this, I'm freaked out. I have never known someone with such trauma, let alone been intimate with him. He is so loving and nonjudgmental towards me, yet I can't help but judge him. I feel terrible for doing so. I love him so much, and I realize he has made positive decisions every step of the way to better his life and break free of the awful cycles he experienced. I'm wondering how it's possible to connect so deeply with someone so different than me.

How can I move forward loving this man I feel so deeply connected to, yet scared by all the baggage he could potentially bring to the relationship? Signed, Head or the Heart.

Wow. Yeah, it looks in Hederhardt. I mean, she's asking a very serious question that I'm sure a lot of our listeners can relate to. Should I be concerned about people's past? Isn't there past? It's their present as well. And should I think about and be concerned about these things? Absolutely. But the guy sounds great. I agree. This letter...

spoke to me because I have to say I am somebody who does have these things in my past. I have suffered really sort of the fallout of a childhood that involved a lot of violence and emotional and sexual abuse, right? And divorce and poverty and all of the different struggles of my past that people who've read my books or listened to this show are familiar with, right? And yet I'm okay. I'm

And I have been really all of my adult life. And, you know, I, of course, went through a very difficult period of my 20s. But I came out of those actually really ready to have a healthy relationship. And I think that Head & Heart is making that little mistake where it's like she's making this very neat equation that if you've –

suffered any kind of trauma, it equals you will perpetuate that trauma in your life. And that's absolutely not true. Now, that's sometimes true. Right. We should say it's sometimes true. You absolutely have to heal that trauma to some extent or to a great extent before you can continue forward in a healthy way. But I have done that. And one thing we know, Steve, you and I are constantly getting letters from people with all sorts of childhoods. And we both know that we have letters from people who had

incredibly difficult childhoods who have become incredibly powerful, wise, resilient adults. And then the reverse is true. People who have nothing back there in the past and they have very, very difficult lives and they struggle in all kinds of ways. And so first I want to say to head and heart, you know, trust yourself.

what you observe and experience with your partner. Okay. If he seems like a great guy, he probably is a great guy. If he seems like somebody who's made peace with his past, he's probably made peace with his past. And she doesn't mention how old he is, but we'll just assume that they're about the same age. She's 34. He's had, you know, at least a decade, more like probably a decade and a half of adulthood to come to terms with that childhood he had. And I

And it sounds to me like this is somebody who has done the work that we so often encourage people to do. Yeah. Well, and I think the anxiety that she's expressing probably is in an exaggerated version what everybody feels when they meet somebody that they have this intense connection to, who they let in to the fortress of their hearts so quickly. Is this safe or is there something lying in wait? Can I trust somebody?

Or am I going to have to brace against the possibility that I'm going to give my heart to somebody who, you know, is not going to be a good custodian, not because he's a bad guy, but because he's gone through some stuff. And there's some baggage that I didn't see when we were in the thrall of those early weeks and months where it's all beautiful and ecstatic. Can I just put like the highlighter pen over that statement you just made? Yeah.

Is there some baggage I didn't see when we were in the thrall of those early stages? The answer is yes. It is always yes. Whatever background you came from, right? Absolutely. But I think that...

She's got to listen to what her concerns are. And she might have a sort of occluded view of them because she came from a background that didn't involve trauma and alcoholism and divorce and emotional violence, it sounds like. But she is smart enough to recognize that, and I think it speaks well of her, look, you can't go through all that stuff and not have it have an effect on you. And I want to make sure that this guy has worked through that. Otherwise, in one way or another, I'm frightened that it's going to crop up. Yeah.

I absolutely understand what you're saying. It could be that this guy is remarkably resilient and has done that work and so forth. But her anxiety is not completely one of a sort of cloistered naivete. I think she's honestly saying he went through some heavy stuff. And I'm wondering if that's going to arise in our relationship.

That's a good, honest question. Okay, well, let's ask her. We're going to do this new thing. We're actually going to sort of break that wall between us and all of the people who have problems. And we're going to call Head or Heart. Hello? Hello? Is this Head or Heart?

Hi, yes, it is. Hi, this is Cheryl Strayed. I'm here with Steve Allman. Hi, Cheryl. Hi, Steve. How are you guys? We're good. How are you doing? Good. Thanks for taking the time to consider my letter. You know, you're the first person we've talked to who's a letter writer on the show.

Really? Wow, that's amazing. Yeah, so this is a historic moment. Awesome. I'm glad I could be a part of it. First, we thought we wanted to get a little more background about your love story. First of all, how old is your boyfriend? Is he your same age? He is 36. 36. And how long have you been dating?

Well, so it's quite new. We've only known each other like a month. And immediately we just had this really like deep soulful connection and just immediately became very close. And like I said in the letter, we both admitted, you know, that we have not felt this before with another person. That is so sweet. So it's been a month, but...

intense, you know, in the best way possible. So how'd you meet? Well, we live six hours away and I was in another part of the state for a work trip. And I just happened to go to this coffee shop on the way home before my six hour drive. And he was there and we just,

And he gave me his name and number like at the end of our quick five minute talk and then connected from there. Wow. Of all the Java joints in this world. I tell all my friends and they're like, that's like a meet you. You know, I'm like, it's interesting because I'm thinking like this amazing person walks into my life and and

And I'm just like in awe, right? Like of the universe that this exists and this has appeared in my life. And I've been thinking like, well, you can't help like who you fall in love with or you don't fall in love with, right? And so how did the issues that you wrote to us about, these concerns about the differences in your past and especially the struggles in his past, how did those start to come to the fore for you? You know, they...

They were brought up initially, like in our early phone calls, just kind of getting to know who each other was and just kind of sharing our story. You know, the way he presents them is just like, this is who I am. You know, it's not like a dumping. It's not like a heal me, help me. It's more just like, this is my past. This is who I am. And so for me,

I did say in the letter that I have some judgment towards him. And actually, I want to sort of tweak that a little. What I kind of want to say more importantly is that in the past, I have judged people like him. But with him, it's different. With him, it's that I more have compassion, but there is still a bit of unease for me because I've never known someone with such trauma.

Well, what about it scares you? Like I said, maybe it could create potential baggage in the relationship, even though right now I have no reason to believe that because nothing he has done, you know, has shown that there would be any sort of that baggage. But I don't know. Like, I just worry if those patterns, you know, like could come up in the future. I guess that's sort of where my fear might come from.

Well, let me just ask a couple of things specifically. So you mentioned that his parents were high-functioning alcoholics. Does that come up in, you know, does he drink? Do you look at him drinking and think, is this an alcoholic lying in wait? You see what I mean? Yeah, that's an interesting question. And he doesn't drink. And I asked him, you know, like, flippantly.

Flat out, I was just like, so what is your relationship with alcohol? And he's like, well, to be honest, I don't really drink. I don't like it and I don't like what it could make me. And I admire that. I think that's super strong of him. What about his relationship to drugs? You mentioned that he's done a fair number of drugs. Is he describing addiction or recreational use?

Um, just recreational use, but it's just for some reason, it just kind of scares me. And I know it's the past and he's not, you know, involved in the same way that he was in the past with those, but it just, he's just a very different person. And it's just very interesting to me how we connect so, so deeply.

Right. Well, it sounds to me like he's a lot edgier than the other people you've dated, at least with an edgier past. And maybe, I mean, you describe such a strong connection. Maybe a part of that, what's connecting you is that he's maybe more interesting to you because he has...

some edge to him. He has some experiences that are outside of what you yourself have experienced, or it seems even have been exposed to. Yeah. And obviously, all those more conventional, kind of safe relationships, you know, didn't work out. Right. And, yeah, like, I noticed sort of this pattern that all of those men were

didn't have this like emotional intelligence, this emotional openness, you know, the ability to like give. And this guy is so giving. He's so open. He's so passionate. And it's like, oh, this is what I've been looking for. But then my head is like, but wait, like he didn't go to college. He has kind of a broken past. So it's like there's this constant struggle between my head and my heart. Yeah. Well, you know what?

I am somebody who also has a broken past. You know, I've experienced many of the things that you mentioned in your letter and other things as well. And I just want to say when I read your letter that

I'm basically in your boyfriend's shoes, right? Here I am, this adult who has this backstory that is full of trauma and hardship and difficult things. And I will say that I actually have come to this place in my own life and certainly in my marriage. I feel like, and I hope this is a consolation to you, that those difficult things that I experienced in the past are

actually made me a better partner and made me a better person, a better human, and really enabled me to do things like this very gig right now, you know, thinking about other people's struggles and secrets and so forth. And of course, that can go the other way, too. I feel like the traumas I experienced informed me.

who I became because I responded to them by really trying to heal my wounds and trying to be resilient and move forward in a positive way. And so I just want to say to you, like, just because this is somebody who's experienced hardship and loss, that doesn't mean that it's going to come up in negative ways in his adult life. Now, it probably will come up.

But think about this. It might come up in positive ways. You know, this is a man who has survived great difficulty and he's managed to do it with a lot of, it sounds to me, beauty and grace. And that's to me, it's like a really amazing attribute. Maybe it's the reason you think he's so amazing because he kind of is.

Yeah, he is. Have you asked him what he's done to heal those wounds of his childhood? Yeah, actually, we have had some really honest conversations, which I am just so grateful for. And so he has, like, he's done a lot of therapy. And I think...

That has really helped him. And also his art. He told me that, you know, the art that he creates is like how he processes a lot of his emotions. I think a mix of those two things have helped to heal him. What do you do for a living?

So I'm a photographer. So you're an artist too. Yeah. And so that's, you know, why I mentioned that in the letter, because I've always been the more unconventional one in the relationship. He's out edged you. Yeah, exactly. I'm like, what? Like he's just so conscious and positive. And I always thought I was that, you know, and he's challenging me already in like so many good ways.

Well, maybe you met your match. Yeah, maybe. Maybe you did. Maybe you did. One thing, too, we talk about this a lot on the show, and I think both Steve and I in different ways have written about this, and that is at many points in our lives, I think we need to

really in a conscious way, take stock of, you know, what are the stories that we've told ourselves about ourselves and about others, and then rewrite that thing. So it sounds to me like you have told your story about what people from a quote, good background, what those people are like, and then what people from a quote, bad background are like. And I think what's going on here is you're finding that people don't fit into those boxes as neatly as maybe you suspected. Yeah.

That in fact, you can be somebody who comes from a lot of difficulty and turmoil and have a very solid, healthy whole life. Right. And you're a perfect example of it. Thank you. Thank you. You know what? I am actually. And I'm proud of that. Yeah. I'm really very conscious of what I've made manifest in my life.

And without knowing this man, and even you don't really know him. I don't mean to diminish the intense month you've had. Obviously, you know him to an extent. But I really think you should trust your heart. I really think you should trust your heart. And that means that, you know, a year down the line, you might find that this guy isn't for you. Time will tell. But I think that, you know, when you make decisions based on ideas you had rather than what's actually before you, that's where you go wrong. Right.

And I think that you should trust this feeling that you have of love and affection and respect and admiration for this man. You know, the other thing to realize is you're so early on in this. So I counsel you to be open and communicative, but also patient. As Cheryl was saying, you're a month into this. And even though you've opened the door pretty wide to this guy and you guys are obviously having these very intense conversations and feelings about one another, be patient. It's a long way to go.

We hope. Yeah. Okay. Good luck and congratulations for meeting somebody fabulous. That's a fun thing. Of all the things you can be bewildered by, this is about as good as it gets. Will you write to us in a year and tell us what's gone on? Sure.

Yes, I will. No, no, actually, you know what? We're going to go ahead and be greedy and say six months. Six months. And then in like two years, Steve and I will come and officiate your wedding. Oh, yeah. Okay. Oh, my gosh. You guys will definitely be invited. And you know what? Just for you, Heather Hart, because you're our first letter right we've talked to, I'll throw in the bris for free if you have a male child. Yes.

Well, thank you for your great advice. I really appreciate it. Thank you. We love to talk to you. All right. Thank you so much. Take care. Bye. Bye. Bye.

Hey, it's Ben Brock Johnson, co-host of Endless Thread and director of digital audio at WBUR. WBUR, including yours truly, is headed back to On Air Fest, three days of podcasting that takes over Williamsburg, Brooklyn from February 19th through the 21st. Want to hang? This year's lineup has some sessions I can't wait to see, like CNN's Anderson Cooper talking with WBUR alum Adi Cornish, also In Polite Conversation with Anna Sale and Death, Sex, and Money, and

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The Emmy Award-winning HBO original series returns. There has been more crime on the island. I'm a little freaked out. What happens in Thailand stays in Thailand. What does that mean? It means we're not dead yet. Amen. Amen. A new season of the HBO original series The White Lotus premieres February 16th at 9 p.m. on Max. One thing that I thought about as we listened to Head or Heart talk is

It was this idea, she says, all my relationships have been safe relationships. And there was a part of me as I listened to how deeply in the thrall of this relationship he was, I thought, well, you're finally in a deeper relationship. And the deeper you get into any relationship, the more dangerous it gets.

And it doesn't have to do with somebody's past as much as it has to do with the present that you're trying to share with them and the fact that you're really laying it bare. This woman sounds like she's been fiercely independent for a long time and defined herself in that way. And here is this guy who is, you know, regardless of where he's coming from, you know, she is deeply in love with him after a month.

I think it's probably an appropriate human reaction to be somewhat terrified by that. I do, too. I'm really struck, too, by, as you know, we have the letters we discuss on the show. And then we have the thousands now of letters in our inbox. And so whenever we have a letter that we discuss, in some ways, they're in conversation with those other letters that we've read. And letter writers. Yeah.

One common letter that we have is from the person who is in love with, quote, the right person. The person who on paper seems like a great match. And for whatever mysterious reason, that match doesn't feel right. And I think in Head and Heart's letter, we have almost this opposite thing. Here she actually has somebody she feels very connected to. And the mismatch is that she has this idea that he's not the correct match.

And I would say to both of those people, those letter writers who were saying, wait a minute, why am I not feeling this thing for this person who's supposed to be perfect for me? And my answer to them is because you're not feeling it. And that part of love is magic and part of love.

The danger, you're talking about that not being safe in a relationship, is trusting that magic, by which I mean the invisible, inexplicable, intuitive, mysterious nature of chemistry and feelings and emotional connection. And in this letter before us, what I really hope is that no matter how this relationship turns out, that we are ultimately always

When we're questioning relationships, we're trying to evolve ourselves. We're trying to grow personally. And what I really hope for Head & Heart is that she takes that idea into her head and her heart. That maybe she will find love, whether it be with this guy or someone else, in a way that's unexpected and that that story hasn't already been written. That she needs to write it herself.

It's such a great idea that part of love is magic. And I would say that the rest of love is hard work. I knew you were going to say that. You knew I was going to say that. You're like the oarsman of the love world. Well, but listen, yeah, I am. You know why? Because it's a long river and you don't know what's coming down the next bend. And she is telling us about the magic and it's beautiful and it's ecstatic.

But underneath that is the thing that fights against the magic because the magic is thrilling and also really scary and destabilizing and makes you vulnerable. And so what do you have as a brook against that? You have the hard work of communicating with yourself and your own preconceptions about who the right person for you is supposed to be and what somebody's past says about their present. And with this guy who clearly is going to be capable, it sounds like, of being honest with her about, you know, what his experiences have been and how he's reacting to her behavior.

Her attitudes that she is carrying in. You're just nodding your head. It's a good thing that one of us is a romantic. I'm a romantic too. Magic is huge. It's all around us. But the rest of it is hard work. Remember that movie Moses from our childhood? I do. There's this scene...

I think these guys are like rowing something and somebody's like whipping them. They're slaves. Is this your conception of Jewish culture? This is like the Cheryl Strayed shit. It's from my childhood. I barely remember it. They're rowing? Do you remember this big ship and all these really buff guys who are rubbed down with baby oil and somebody's whipping them? Yeah, that might be Spartacus. I think it's in Moses. You think it's in Moses? I don't think they're working. That image came to mind. But you're right, you're right, you're right. But sometimes we need to...

Forget about that. She's not in the moment of hard work. She's in the moment of love. Just love. Just love. Trust love. Will you not give me that?

I think she's mistrusting it. I think there's a voice inside of her. That's why we have her letter. Cheryl, if she was in the middle of feeling that magic and love, we would never have spoken to her on the phone. But there's some voice inside of her that isn't going to be defeated by the magic. The magic's there in spades, in abundance. And there's still that voice of doubt and anxiety and whatever she's carrying. That's her baggage, basically.

And then she has to do the hard work of communicating that to him and within herself and working through it. It would be great if you could snap your fingers and make everybody's ambivalence about something as terrifying as love go away. But we don't have that power. You have that power, but you only use it in limited cases. Okay. You know me. You know my way. You just can't show me. But God, I'm praying that you'll find me.

Well, Dear Sugar Radio is produced by the very romantic and magical WBUR in Boston. But who does the hard work? After you make the magic, Cheryl, who does the hard work? The person who wields the whip.

produced and edited by Lisa Tobin. Yes. We're recording at Talkback Sound and Visual in Portland, Oregon. Yes. Our engineer is Josh Millman. Yes. Who, you know, the jury's out. Is he a romantic? Not? You know what we should do? We should have people write in and they can just write in to dearsugarradio at gmail.com and they can just write in hard work or magic. Okay, let's do it. I'm going to win.