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January 2, 2026 10 mins

Chelsea and Catherine get an update from a caller who married his longtime love and assess a friend-zoning situation.

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Need some advice from Chelsea? Email us at DearChelseaPodcast@gmail.com

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Executive Producer Catherine Law

Edited & Engineered by Brad Dickert

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:01):
Hello, Gatherine.

Speaker 2 (00:03):
Oh, hi Chelsea, how are you.

Speaker 1 (00:05):
I'm feeling very deep throated today. Yes, I counted him too.
I don't know, is it the weather. Maybe maybe I
spoke to a little bit of a joint.

Speaker 2 (00:13):
So well, I have a really fun update. So I'm
not sure if remember Wit from our John Lovett episode.
He was getting serious with his girlfriend and wanted to propose,
but wasn't sure about telling her family that he's trans Oh, yes,
I remember. Yes, we loved Wit, and I think we
did update that they got engaged and that was all

(00:34):
very happy. So I got a very special email this week.
This email is from Aaron. So Aaron says, Hi, Chelsea,
I couldn't help but think of you and the experience
you shared with my son Wit when he appeared on
the Dear Chelsea podcast last year. This is W's mom.
I've been a longtime listener of Chelsea's podcasts and have

(00:56):
enjoyed her episodes on Netflix and YouTube for years. Whit
and Ive Binge watched some of them together when I
visited him in Montreal. So I was thrilled when Catherine
arranged for Wit to be on the show and have
the chance to ask Chelsea and John questions about his
dating relationship. Shortly after the episode aired, Wit proposed to Anne.
She said yes. The heart of the episode was about
whether Witch should tell Anne's parents that he's trans before

(01:17):
they got engaged. Chelsea and John suggested it really shouldn't
matter either way. As it turns out, Anne's parents are
incredible people. They were extremely understanding and expressed that they
were honored Wit and shared that part of their story
with them. They emphasized that it didn't change how they felt.
It simply didn't matter to them in the best way.
WIT's experience on Dear Chelsea gave him confidence and validation
beyond what I could have imagined. The respect and dignity

(01:39):
Chelsea and John brought to the conversation through their openness, inclusion,
and compassion was truly refreshing. As WIT's mom, I want
to say how much I appreciate all of you. Today
I'm flying to Montreal for Wit and Anne's wedding, and
I felt it was the perfect time to reach out
and express my gratitude for the kindness you showed warmly.

Speaker 1 (01:56):
Aaron, Oh my god, wow.

Speaker 3 (02:00):
I know it's just like so keeping families together, That's
what we're doing keeping families. I mean to get a
thank you letter from someone's mother, It's like the best
gift ever.

Speaker 2 (02:11):
I know, it's so delightful, So thank you so much
for writing in.

Speaker 3 (02:14):
And by the way, what a beautiful model and blueprint
for anyone's Yes, who is dealing with anyone. You know.
The way that this couple reacted to finding out that
their new son in law is trans is so beautiful,
like it has absolutely no impact on them, and then
they thanked him for sharing something so personal.

Speaker 1 (02:35):
That is how we treat people.

Speaker 2 (02:38):
And for Aaron to be obviously this woman who is
has a child who maybe things went a little differently
than expected as we grew up. But guess what Aaron
loves with and you know, is accepting and these families
have come together.

Speaker 1 (02:51):
It's just beautiful. It's just awful.

Speaker 3 (02:53):
This is the way the world should be going around.
Everyone should be accepting of everybody, regardless of what anything,
be able to accept and look at everybody as a
human being.

Speaker 2 (03:03):
Yeah, well, Ricky says, you're Chelsea. I've been a fan
of Chelsea since the Chelsea Lately days. My sister and
I would chat recapping your hilarious shows.

Speaker 1 (03:16):
Often, and we saw you live in New York many
years ago.

Speaker 2 (03:18):
Anyway, I recently came across your podcast and have been
listening and loving hearing the humor that I always enjoyed
with my sister. Anyway, I don't need advice, but I
have a ridiculous question. Pikachu versus kosloppus. Why do you
sometimes say one versus the other? Different words, same meaning
or is there more of a distinction? Just stupidly curious?
Thanks Ricky, great question.

Speaker 1 (03:38):
I love it.

Speaker 3 (03:39):
Pikachu is just a softer way to say I feel
like caspis sounds like sloppy sea bass like it sounds
like fish, you know what I mean. Cass is like yes,
it's like, oh you have a cute little you know.
That's nice way to save vagina. It's the nicest way
to save vagina. Vagina's a terrible word. It's not good.

Speaker 1 (03:58):
And so Pikachu. I don't like the word pussy.

Speaker 3 (04:01):
I mean, I like calling men pussies, but I don't
like saying, you know, come like my pussy?

Speaker 1 (04:07):
So gross?

Speaker 3 (04:09):
Should we name this miniesot like come like my I
can't even repeat that, so.

Speaker 2 (04:13):
I'm gonna have to use too any asterisks of what
do that? Yeah, and our family it's tooty, but it
wasn't when I was growing up. That came from like
my sister's college friend. But now we call it a tooty.

Speaker 3 (04:21):
But tuty is a fart also like a toot you know,
in some families.

Speaker 1 (04:26):
It could be.

Speaker 2 (04:27):
When my family growing up, my parents called it your body,
which is very confusing.

Speaker 1 (04:31):
Like that is absolutely the wrong, Like call that your body. Oh,
make sure to wash your body. No, that doesn't work.

Speaker 3 (04:38):
I like beaver also, but that's not for you know,
I mean everyday consumption.

Speaker 1 (04:43):
No, it depends.

Speaker 3 (04:44):
I mean, I guess for me it is I can
pretty much say, I mean, there's nothing wrong with beaver,
but actually make a note to myself to start using
beaver more often.

Speaker 1 (04:52):
Well, our caller today is Liz. She says, you're Chelsea.

Speaker 2 (04:57):
About six months ago, I broke up with my first
long term boyfriend. He was not good for me, and
it took me a while to realize it. The relationship
ultimately ended because he wanted me to convert to Catholicism,
but truly he wanted my leftism politics to more align
with his right wing tendencies. Looking back, I can now
see his behavior was controlling and somewhat abusive at times.
He was the classic love bomber that withdrew whenever he

(05:18):
couldn't get control of me in some way. There were
times I'd call him out for attempting to gaslight, verbally, intimidate,
and physically control me. He would always become super defensive
and try to put the blame on my mental state
rather than take responsibility for these things. Needless to say,
after getting out of that relationship, I've been in somewhat
of an apathetic state about men since the breakup. I
want nothing to do with any characteristic of my ex,

(05:40):
so I've been mostly going out with guys, knowing that
it will lead nowhere. Well, I met a really sweet
guy on the dating apps. He seems the complete opposite
of my ex. We're politically aligned, share a ton of interests,
and he puts in a ton of effort. The problem
is I'm not that attracted to him. I totally want
to be, but I've given it a few months and
still feel.

Speaker 1 (05:57):
No attraction to him.

Speaker 2 (05:58):
My question is, am I just continuing my patterns of
falling for unhealthy relationships due to my insecure, anxious attachment style.
On paper, this new guy has everything I should be
looking for, but I can't help a feeling there's a
lot of the chemistry missing.

Speaker 1 (06:12):
This leaves me thinking about the chemistry I had with
my ex.

Speaker 2 (06:14):
I know that relationship wasn't healthy, but why do we
look back with blinders feeling like that was the relationship
that had something When the new guy on paper looks
so perfect? Do you think I should give up on
this new guy and keep looking for someone I'm more
attracted to. I'm a little scared that my little self
quote unquote is calling the shots, and the reason I'm
not feeling the attraction is because I'm still drawn to
the avoidant, controlling person.

Speaker 1 (06:35):
Liz, Hi, Liz, a little chelthy.

Speaker 4 (06:39):
Hi.

Speaker 3 (06:40):
Okay, So, first of all, I think you're doing this
is great. There's so many people that call in and
they don't even know how to begin the process of dating,
and I'm so glad that you're already doing it and
you understand what you're that you're avoidant?

Speaker 1 (06:51):
Anxious or anxious avoidant?

Speaker 3 (06:54):
Is that what yeah you said, Okay, anxious avoidant that
you got away from that ex boyfriend, that's over what
you're realizing is that you don't have chemistry with this
new guy. That's okay. You don't have any chemistry with him,
then that's it. There's nothing happening there. But don't confuse
the chemistry you had with the other guy as a
sign that you should be with that guy. You just
know what chemistry feels like and what a good guy

(07:16):
feels like. So you are I have identified all of
the things that you want in your romantic relationship.

Speaker 1 (07:23):
You want somebody who's reliable.

Speaker 3 (07:24):
Who's good on paper, who's going to be honest, who's
going to be thoughtful and caring and not manipulating and
not controlling, and you also want to have chemistry.

Speaker 1 (07:32):
That's great, that's a victory.

Speaker 3 (07:33):
You know exactly what you want and you're going to
find it, and it's just a numbers game. And don't
stay with some guy that you're not attracted to. There's
nothing you could do about that. You've given it a
couple months.

Speaker 1 (07:42):
If you would give it, if it were three weeks,
i'd say give it a couple months. But you've given
it a couple months. You've tried. You're not attracted to him.

Speaker 3 (07:48):
You don't have to be attracted to everybody I wish
I could be attracted to more people, do you know
what I mean? I'm sure you feel the same way.
I'm like, oh God, I wish I could be attracted
to you.

Speaker 1 (07:58):
You seem easy.

Speaker 3 (07:59):
But we've identified all of the things that you're looking
for in a relationship. You're winning, You are winning, You
are on your way to finding somebody. Just stick with
it and just know in your heart what you're going
to say, what you're going to settle for. You're not
going to go back to a guy that's controlling or
domineering in any way, and you're not going to settle
for somebody that isn't exactly what you're looking for.

Speaker 4 (08:21):
Yes, I knew you would say something just like this, Chelsea,
but it was making sure that I wasn't, you know,
just writing off this new guy because I'm looking for
something else. But no, I think, I think, I know.

Speaker 1 (08:34):
I just need to hear it.

Speaker 3 (08:36):
I guess, yeah, and listen, if you end it with
this guy and in a couple of months you're still
thinking about him, then guess what, Then you can go
back and go, god, wow, I made a mistake. Yeah,
So yeah, just trust yourself, really trust yourself and listen
to yourself. You're identifying all of the things that are
important to you in a relationship, and that's you're ahead
of the game.

Speaker 2 (08:56):
Yeah, And I think like teasing a part that idea
of having chemistry with someone from what you had with
your ex, which was not just chemistry. I'm sure you
had that too, but what he also gave you worth
these like adrenaline hits and dopamine hits of I never
know what's coming next, Like when you have those arguments
with people and they have your nervous system all out

(09:18):
of whack, you are getting rushes of adrenaline every single
time that happens. So that can also be very addicting.
And that's a different thing than just like having chemistry
with someone. At the same time, if you don't have
chemistry with this new guy, you don't have it's friend zone, right.
But at the same time, you may find dating someone
who's like this guy that you do have chemistry with,

(09:38):
and you find yourself like, is this person.

Speaker 1 (09:41):
Too boring for me?

Speaker 2 (09:43):
That I think is the thing you want to maybe
give a little more time to. If you find yourself
feeling that because you're not getting those dopamine and adrenaline
hits of just like surges of hormones, right, and sometimes
like the steady eddies at the beginning, you can be like,
is this boring?

Speaker 1 (09:59):
Or is this? This is just kind of fine?

Speaker 2 (10:01):
So maybe give yourself a little more time if you
find yourself in one of those. That's but that's what
you're aiming for, right, somebody who's not constantly a rollercoaster.

Speaker 4 (10:09):
Sure, yeah, that makes sense a lot of sense.

Speaker 2 (10:14):
Okay, Liz, you have some friends zoning to do.

Speaker 4 (10:17):
Okay, you forgot it, got it?

Speaker 1 (10:20):
Thanks for going so much. I just announced all my
tour dates. That's called the High and Mighty Tour.

Speaker 3 (10:26):
I will be touring from February through June.

Speaker 1 (10:30):
So go get your tickets now.

Speaker 3 (10:31):
If you want to come see me perform, I will
be on the High and Mighty Tour.

Speaker 2 (10:36):
Do you want advice from Chelsea? Right into Dear Chelsea
Podcast at gmail dot com. Find full video episodes of
Dear Chelsea on YouTube by searching at Dear Chelsea pod.
Dear Chelsea is edited and engineered by Brad Dickert executive
producer Catherine law And be sure to check out our
merch at Chelseahandler dot com
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