Forever Alone? (Part 1)

As the saying goes, “There’s a lid for every pot.” There’s someone for everyone. Chelsea has been looking for her lid — her someone — since high school.

Nearly 15 years after her only real relationship ended, Chelsea still hasn’t found her person. It’s not like she hasn’t been trying, and it’s not like her life is totally miserable … but in case you haven’t had to date lately? It’s exhausting. And sometimes demoralizing.

Transcripts may not appear in their final version and are subject to change.

NARRATION
When I was 16, my first boyfriend broke up with me. He actually broke up with me like 600 times over the course of the next 8 years, but this was the first time. And it hurt so bad I thought I might die. One night, before we left for his football game… though he had dumped me… I cried and cried in my room to my friend Erin. “What if he’s the only boy who would ever love me?” I wailed. And I meant it: what if, out of the billions of people on Earth, I had found the ONE who would love me on orientation day of high school. And he was the ONLY one who could ever love me, and he decided not to? Would I be alone forever? My friend Erin was like, WHAT? Are you insane? I never want to hear you say that ever again. What a good friend! I may not have ever said it out loud again, but I certainly let that feeling return to me over the years. That feeling – that maybe, at my core, I was not actually loveable, that any affection I received may be my last opportunity for love – led me to many, many mistakes that are not worth detailing right here. We’ll save them for another episode.
The last time we mentioned relationships on this show, I got an email to the effect that being single – being lonely—doesn’t compare to the death of a person. I just want to say, um, says who? Says a person who is assuming there is a standard barometer for suffering. For the record, and I’ve said it before, but apparently not clearly enough: I refute that notion. I am not here to make a show that ranks your tragedy against every injustice in the world. I’m here to make a show that …does the opposite of that?
So, this is a relationship episode. An episode about TRYING to find a relationship. An episode about my friend, Chelsea. And HER search for love.
Chelsea: People ask me all the time what’s your type. Emotionally unavailable is always my answer.
[MUSIC]
Nora: You are to me like you are color.
Chelsea: I love that. Thank you.
Nora: You are. Every once in awhile I’m like should I be like all of these like trendy minimalist brands and only own nine pieces of clothing that are all neutrals. And then I look at my closet which is modeled largely after our friendship. And I’m like nah. No.
Chelsea: I love it. Thanks for that.
Nora: Chelsea why are we talking today? It’s not just for sweaters and the fact that we have been friends for a few years now.
Chelsea: [00:01:04] I am not totally sure I think I know and… I and I’ve been summing it up as like a perpetual singledom maybe. Being like sort of like officially in my 30s and not having like ever been in a long term relationship.
Nora: [00:01:31] You had one long term relationship.
Chelsea: [00:01:37] One in high school that was like a year long Yeah yes. Yeah.
NARRATION
Okay so one high school boyfriend. That’s not too shabby. You need to know that Chelsea is 32. Making her last long-term relationship over a decade ago. And… maybe you also need to know that she’s a REALLY talented graphic designer. That she looks like Linda Ronstadt in the early 70s like… cute little bangs, adorable face. That she’s the kind of friend who will drop everything to run to your house and watch your kids on a Monday night even when she has 10,000 other things to do.
Maybe you already have a friend like Chelsea. Maybe 5 or even 10 friends like Chelsea. Personally, I have a LARGE HANDFUL of women (and a few men) in my life who are TOTAL AND COMPLETE CATCHES. The kind of people where you’re like, oh my gosh, it makes NO SENSE THAT THEY ARE SINGLE. What is wrong with the world that she isn’t the Bachelorette? That men aren’t begging at her feet for the opportunity to be humiliated on national TV for her affections?
It’s not just me who feels this way about Chelsea. Across the board, the reviews are unanimously 5-stars. Two thumbs up. Chelsea is the best.
[[[WANT A LITTLE SOMETHING TO CONVINCE US HOW GREAT SHE IS]]]
See??? Chelsea’s great. We all agree.
[MUSIC]
My father used to say, “there is love for everyone in this world.” And I believe that. I believe it so much. I’ve said it to myself a million times. To friends. To strangers. To all of you! And I say it to Chelsea. Every time she goes through another cycle of dating. Chelsea: [00:14:07] I’ve gone on lots of dates. You know what I mean but I haven’t like dated lots of people like I have this very specific formula that happens in my life, that’s like we’ll go out like maybe twice or like we’ll go out enough to like be intimate and then all of a sudden they fall off you know. And it’s just like I really want to be your good friend and I want to be in your life. But I like don’t want to have sex with you. I’ve had to actually I’ve dated a lot of dudes that were like go back to the person they were dating before which is also just like really sad. Or like dudes that are like now married to like the person they were dating before me. Like I recently dated a guy who was like I think you’re great. I think you’re amazing. I think you’re incredible. Like I want to date you I am physically attracted to you but I’m depressed you know and I can’t get past that. And that’s hard too because like as a woman I think especially you know it’s like I want to help you fix that you know like I’ll get you through that. I know what it feels like to be depressed. And I can help you know. But ultimately like I’m not responsible for that, you know. But then I like kept hanging out with him of course. You know when it was convenient for him because that’s how you know that works. And he… the last two times I hung out with him he was on his phone the entire time like with his ex. Wow cool. And I did that twice not just once. It didn’t take just once to be like… bye..
NARRATION
Chelsea and I have talked about this for years — not always in front of a microphone — and it seems like all of her not-quite-relationships follow something that I am calling…
[MUSIC]…
Chelsea’s Proven and Patented Seven Step System For Not Ending Up In A Happy, Long-Term Relationship.
[BUTTON]
You could just call it a pattern. [MUSIC]
Chelsea: [00:59:15] OK. Yeah I would say step one is finding someone who I find physically attractive I think that’s so rare. Like I rarely am attracted to another human being which is maybe weird. I don’t know. I don’t know how… It just doesn’t happen often. Chelsea: [00:59:15] Step two. Step two… Usually it’s someone I’ve met through a mutual friend or acquaintance or in a public setting. We talk, we exchange numbers.
NARRATION
I love matchmaking. I am ALWAYS on the hunt for the perfect match for my single friends. I am always looking out for them. And about a year ago, I found someone for Chelsea. And I thought I had done it. I had solved it. And… this story is a perfect example of Chelsea’s pattern.
So here’s how it went… I took care of Step 1 and Step 2 in one heroic move. I took Chelsea to my co-working space, where there was this really great guy I’d met a few times. Just, a solidly good dude. Who happened to be there. And we all sat together and talked and when we left I texted him to ask if he had plans…
Chelsea: [01:18:02] No no no not how the story goes. You handed me your phone and made me text him as you being like Hey so Chelsea is here and she lives in Long Beach but she’s here and I think you should take her out on a date. What do you think. Basically.
Nora: [01:18:20] Right… I… OK fine. I… So I dictated a text message to you only because it was going to make the McDonald’s drive through.
Chelsea: That’s true. That is true. NARRATION
Okay. So. This is exciting, right? Chelsea has reached Step 3. Chelsea: Step three we know maybe text flirtation if you will and sort of building that anticipation for a first meeting.
Nora: [01:19:09] And… you had to go back to Long Beach and you two were exchanging like very well-crafted playlists.
Chelsea: [01:19:22] Yeah it was fast. It was just like fully fast.
Nora: [01:19:25] And I supported that. I was like it’s the only way to you know fall in love is like you know like you’re falling on the ice just go.
NARRATION
Step 3: textin and flirtin. Now, onto step 4. Chelsea goes out with this guy. Chelsea: Step four a first date and usually a first date for me last no less than… a great first date will last no less than like four or five hours… talking about… about all kinds of things and maybe I’ll cry on a first date. Why not? You know because it feels right.
NARRATION
And their first date was amazing. I watched her on Find Friends just to make sure I knew her location at all times. I could tell, watching that blinking dot? She was having a good time.
And now we’re at step 5. Chelsea: And then step five will maybe be a kiss at the end of the night or maybe if we’re like really getting along like it’s very rare that I would like you know spend the night with someone on the first night and sleep with some one on the first night. But sorry mom.
Nora: [01:01:18] It’s rare.
Chelsea: [01:01:21] But it’s happened. And…
Nora: [01:01:23] We said it’s rare.
Chelsea: [01:01:25] It’s very rare.
NARRATION
We’ll just leave that one there. Sorry mom.
So now… Step 6. Chelsea: step six then would be you know maybe another date… NARRATION
Step 6 in THIS CASE is going to take us into serious rom com territory
Chelsea: [01:19:32] And then he had told me on our first date that he had to go to Cairo for work and that he goes to all of these places studying what he studies which is like all very cool and interesting but he goes to all these world cities and he’s always by himself you know and how cool it would be to have a partner with him to like experience these things. So his mom and sister were going to go. They couldn’t go and he was like I feel crazy because we’ve only been on one date. But like w ould you want to go to Cairo in like three weeks and I was like I don’t know where my passport is actually. It’s a problem but I bet I can find it.
Nora: [01:20:36] And I said yes you are going. Yeah you’re going yeah.
Chelsea: [01:20:39] Everyone said yes even my mom… who I was very afraid to tell and even kind of my dad was like on boardish.
NARRATION
And her matchmaker — me — i was mega on board. Like, duh, GO TO CAIRO WITH A MAN YOU BARELY KNOW! IMAGINE THE STORIES YOU WILL TELL YOUR GRANDCHILDREN!!!! Chelsea: [01:20:39] But I told him that the deal was I think that he needs to try to come to L.A. in that three week period so that we could at least have like hung out twice before we got across the world together.
Nora: [01:21:01] That’s my threshold.
Chelsea: [01:21:02] And then he was like absolutely. Like that’s a lot like and I… but you know thank you for asking for something that you wanted was his exact phrase. And I was like yeah cool feeling great feeling great about this. And he came… and we had a good time…
NARRATION
And away they go. Step 6 of 7…a second date in Long Beach, a whirlwind trip across the globe… careening towards an inevitable conclusion of romance and adventure.
Romance and adventure is also where we are also headed, because we’re going to take a quick break.
[[MIDROLL]]
NARRATION
PROMOTE SOMETHING
[[MIDROLL OVER]]
NARRATION
And… we’re back.
Chelsea was…just, throwing herself in. I told her, look, just go with it. I personally felt very good about sending her halfway across the world with a guy she had seen a few times. It felt like she was embarking on a big adventure. LIke she was on the precipice of The Big Relationship we’d been waiting for her to find.
Chelsea: [01:21:29] We flew to Cairo together. It was a super intense like work situation for him. And I think he was just like really nervous and overwhelmed and it was harder than he thought it was going to be. His Like greatest mentor in life was on the plane. And we ended up sharing like a cab to the hotel with him and had dinner with him and immediately like our situation became more serious because he had this guy with him that was like someone he really looked up to and he didn’t want to be like I’m just on a date with this girl. A third date with this girl. NARRATION
This is where the rom com hits the road. Like, okay, in THEORY? It sounds very romantic to fly to Cairo with a man you barely know. In REALITY? He IS on a work trip. You barely know each other. And now you’re in very close proximity to his esteemed colleagues. And because unmarried couples are frowned upon in Cairo, you also have to pretend to be married? Like with a pretend wedding ring and everything.
Chelsea:It was kind of like oh shit like this. Like is she my girlfriend like like how do I introduce her like who is she to me. And I think he’s a very sensitive person and that like kind of really messed with him mentally a lot and then yeah we got to this place where we finally had a night together and he was done with work and we had the most intense debate I’ve ever had on a date or like even with another human in my whole life about art and what it means to be an artist. And we both were very passionately on different pages about that and it was really interesting and cool and like kind of brought us together in a really beautiful way that I will forever cherish and like it did it like fuel any sort of like romantic fire. NARRATION
As a narrator. As a friend. As a woman. I want to interject and say…what?? YOu fly around the world and instead of Frenching in front of some pyramids you’re debating ART? Okay. Okay. I can roll with this. Chelsea: The next night we had an exhausting day and it was just like we’re laying in bed and I was like I just need to you know sort of bring up the fact that we like haven’t been physical at all on this trip like we haven’t kissed we haven’t nothing you know and he’s just like I just am not feeling it and I think there was a lot of pressure around like making it like this fairytale situation. Like he was like really mentally like fucked up about like everyone is expecting us to come home and be in love now. You know and he was just like I just and I’m not you know and he’s like but then we had this situation last night where we like were so on different pages. And like came together at the end being like wow we disagree very very much on a situation but we still like really admire each other and like like each other and he was like that’s what love is. You know it’s just like disagreeing with someone but like finding some sort of common respect you know and I was like yeah that’s cool. It’s really cool. So like what’s missing you know.
NARRATION
And with this. We reach step 7. We always reach step 7.
Chelsea: Step Seven immediately after Step Six is like oh I’m… I really think you’re an incredible human being but I’m just not that into you.
NARRATION
All that excitement. All that adventure. All those PLAYLISTS, and it ended the way every other relationship did. A guy who wasn’t ready. For reasons. A friendship. But not a relationship.
Chelsea: [01:24:24] I think it was… like him. Yeah. It was totally him because I was very much like I think it would be cool to like date like this seems like a really good cool fit. You know.
Nora: [01:24:38] That was like the most unreserved I’ve ever seen you about anybody.
Chelsea: [01:24:41] Yeah. Yeah. I yeah I was just like I wanted to try and he just was not. But again it was like he wasn’t in a place you know. And I believe that… and he’s got a lot of you know his own kind of like I don’t want to say demons like what’s a good word for like not demons but just like his own kind of issues issues.
NARRATION Instantly, my credibility as a matchmaker was damaged. And I felt my heart breaking for Chelsea. Because even though I KNOW it isn’t that she’s unlovable, what she sees when she looks around her is…everyone BUT her finding love.
Her recently divorced friend has been on a string of dates with men who desperately want to be in a relationship with her.
And the men who have been a part of Chelsea’s 7 step pattern? The ones who weren’t ready for a relationship? They ended up in relationships. Just, not with Chelsea.
Chelsea: [01:25:10] I mean and I’m saying that because like I have my issues we all have our issues but it’s hard for me to not be like I just wasn’t good enough for him. You know I what I like I always want to be the girl that like helps like is the one that a dude decides to just like let it all go for you know and I think that’s the hardest part. It’s like never being that girl and like kind of always seeing like being aware of like who the girl ends up being you know like…
Nora: [01:26:01] What does your brain tell you the difference between you and those women?
Chelsea: [01:26:09] I don’t know. I mean I think part of me does feel like they’re the easier choice. In some way.
[MUSIC]
NARRATION
At this point, you might be thinking: okay, well what’s wrong with her? Is she ugly? Does she smell bad? Is she actually gay? Is she bad in bed? Is she too needy? Too aloof? What, exactly is wrong with her? Because SOMETHING has to be wrong with her.
The answer to all of these, by the way, is no.
Which makes the real question, Why should It Matter???
We all know plenty of awful people. Plenty of smelly people. Plenty of mean people or needy people or aloof people who have found love. We all know plenty of lovely, kind, generous people who haven’t. And for women we are SO fast to try to find fault. Nobody is like, wow, George Clooney must be really clingy and annoying and that’s why it took him so long to settle down. But we’ve turned Jennifer Aniston from America’s Sweetheart into America’s Sad Spinster. Women can’t be single without being a sad story. Like finding love is a measure of your personal worth, instead of a measure of your immense LUCK.
Because that’s what it comes down to, don’t you think? That you would find a person you can love, out of all of these billions of people, and they would love you back? And that you would both be alive at the same time? Both in the same second grade play, or high school geometry class or the same party on the same night, standing alone at the same time? That you would both find each other attractive? Or be single at the same time? The issue is never just YOU. The issue is YOU plus a billion other factors.
So… whatever you’re thinking about Chelsea, or any other person who is looking for love and hasn’t found it? They’ve already thought of your criticisms. And a hundred more. Chelsea: I don’t know I’ve created like a million stories in my head for why you know it’s like oh I’m you know too… um…
[MUSIC]
Chelsea: [01:33:16] I’m not pretty enough maybe I’m too pretty I’m too anxious I’m too weird. I’m great then I’m too successful. I’m not successful and I don’t have enough interests. I don’t have any hobbies and I don’t know their favorite book. I don’t you know I can’t relate to them on some certain level. I am not funny enough… yeah. I’m I’m not interesting enough I think it’s like the biggest one. I’m not impressive enough or I’m too impressive. I make too much money. I have too many nice things in a weird way. Sometimes maybe I’m not opinionated enough or I’m too opinionated. I’m too brash. Nora: [01:32:19] Audience groan. But don’t be too much of anything right. Little girls don’t you dare be successful.
Chelsea: [01:32:25] Right. Don’t you dare have your own life. But I do think that that does that scare men. I don’t know. I think some, plenty of them.
NARRATION
And those doubts and reasons easily eclipse the other things about you. The ones that you like about yourself.
Chelsea: [01:34:27] I think that I’m really loyal. I can’t even say anything good about what it’s all about like wanting to cry. That’s like really sad. I care deeply about the things that I care about. I like that I have my own aesthetic like I have my very own view of the world that is special and I like it. I think sometimes I’m kind of funny though. Nora: You are loyal you’re a very good friend.
Chelsea: Thank you. But I think I always think that fear of like letting someone in till I find out that I’m not all things that they thought I was in some way you know or like… yeah like letting someone in deep enough to have then like be sort of turned away. And I feel like that’s where I get to a lot. You know in the pattern too is just like feeling like I’ve let someone in enough to be like oh nope you know. No thanks. So.
NARRATION
Yes, the wisest souls among us have told us time and again that to find love, we have to love ourselves. And oh my gosh is that catchy. And possibly it is even true. But I have found love when I was nowhere near in love with myself. I found my first love when I was so self-conscious I could barely walk down the halls of my high school without wanting to melt into the actual wall. I found my first husband when I was anything BUT in love with my life. It was actually just a few days after I had walked home from work, through the streets of downtown Minneapolis, openly weeping. Calling my friend Dave to say that I was too exhausted to ever date again. Too sad and tired for love. I found my current husband (that sounds weird but is accurate at the time of this recording. Matthew is CURRENTLY my husband. By the time this airs…who knows!) when I was so deeply grieving that I was putting myself to bed with Tylenol PM and white wine.
Saying “oh, you should love yourself first” or, “you should be happy!’ is a lot of pressure to put on someone. It’s a lot of should.
My producer Hans’ grandma is 96 years old. He visits her every week. He also wrote this part of the narration and I think he’s gunning for some sort of prize. Anyways… you know what Hans’ grandma says to him? “Don’t should on yourself. And don’t let anyone should on you.”
Chelsea: I always go to a therapist and I’m like OK like I see this problem. I’m aware… you know but I just like fully struggle to just like let go and… you said to me once and that like imagine what could go right. I think I’m like afraid to be happy. Like I don’t know what that feels like. And I think you just kind of get used to like a little bit of numbness in life that like… it’s hard to let go of. Chelsea: like I kind of see myself as like not… not as a physically attractive person you know or a person that’s like sort of worthy of like that kind of… affection and you know what I mean even though like it’s something that is very and still like a very uncomfortable space for me. And so I think that that’s something that someone can sense. And like I think I need to find someone who is kind of comfortable with that that someone I can be like super honest with and like
NARRATION
You know why I wanted to talk to Chelsea? Or why I wanted to create this episode? Because love is important to EVERYONE. The SEARCH for love is important to everyone.
This quest is the foundation of the world’s greatest stories, and Taylor Swift’s greatest album (RED, by the way).
It doesn’t always end well for everyone. It doesn’t always END for everyone. Some people are just forever alone. Some by choice. And some not by choice. Like, watch my new favorite show, 90-Day-FIance, and just…you will understand how far people will go for love.
THAT is why we say congratulations when people get engaged, even when the person who just got engaged is a stranger we’re meeting for the first time at a coffee shop while writing this very episode – congratulations, Meredith! We say congratulations because even if finding love wasn’t hard for us – because we met the love of our lives in second grade. Or in high school geometry. Or on Match.com. We MET them. Of all the people in the world, we found one to love, who loves us back. Not THE ONLY one…. 16yo Nora… – but ONE. And we know that makes us lucky. Not because we are hard to love (although, I certainly am), but because it really is like winning the lottery.
Because even if my dad was right – and I think he was – even if there is love for everyone in this world, finding it is still something to celebrate, and searching for it is still worthwhile. And not having it doesn’t mean that your life is worthless, or miserable, but…maybe it would be better if you had a lid for your pot. Or a pot for your lid. Or a lid for your lid. Chelsea: It makes me sound like I just go around and like a very sad state all the time which I wouldn’t say is the case. You know, but it is just like a certain part of my world that is like certainly a struggle.
Finding love is NOT, I repeat, a measure of your personal worth. But it’s also OKAY TO WANT IT. It’s okay to want things! And I know that Chelsea wants love. And I want that for her. So I kept looking. And I found someone for her. Someone fun and smart and kind and thoughtful and loving. Someone who she could be comfortable and honest with. Someone wonderful and kind and loving. Someone complicated.
And you’re gonna meet him.
Brian: Well… I’m an addict. Alcoholic. That… it creates a lot of issues… for me by myself… and in a relationship with Chelsea. NARRATION
You’ll meet him next week, though.
[CREDITS]
This has been Terrible, Thanks for Asking.
I’m Nora McInerny.
Our Senior Producer is Hans Buetow. That’s a thing.
Our intern is Jeyca Maldonado-Medina.
Special thanks this week to Sasha Aslanian, Suzanne Pekow, Jeffrey Bissoy-Mattis, and Hannah Meacock-Ross. And to Kate O’Reilly, Keeley Dunn and Kelly Gritzmacher for heeding the last-minute call to send me all the reasons why Chelsea is wonderful. Our amazing theme music was composed… AND PERFORMED AMAZINGLY… by the amazing Geoffrey Amazing Lamar Amazing Wilson.