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Anna
York drink responsibly hi bitties welcome back to this week's episode of brutally anna we are going to talk about the art of dining alone and redefining community but before we do that i just want to say happy october it's not.
Dave's Partner
Actually october yet as of recording this i'm recording this on tuesday september thirtieth.
Anna
But it will be october by the time you hear this and by then i hope it will be a little bit cooler because it is currently eighty degrees today and in connecticut where i live and speaking of where i live we moved to connecticut five years ago.
Dave's Partner
In the middle of the pandemic and.
Anna
Dave and i moved out here for his job and his job alone really he had lived in new york city.
Dave's Partner
For thirteen years before that i had lived in the city for eleven years.
Anna
And honestly we might still be there if it wasn't for the fact that.
Dave's Partner
The pandemic just upended all of our.
Anna
Lives dave had been doing the reverse.
Dave's Partner
Commute between the city and connecticut for ten years before we moved up so.
Anna
We live near grand central for those.
Dave's Partner
Of you who are not familiar with the mechanics and the geography of new.
Anna
York city basically instead of what everyone.
Dave's Partner
Else does which is commute from the suburbs to the city he spent his twenties and early thirties commuting from the.
Anna
City to the suburbs because his office.
Dave's Partner
Is in the suburbs of connecticut and he was like well i'm young wild.
Anna
And free and i want to live in manhattan and that's exactly what he did so for a decade he had an hour and twenty minute commute one.
Dave's Partner
Way which is actually insane to me.
Anna
But he was always like well it.
Dave's Partner
Wasn'T that bad the train was relaxing.
Anna
I could read or listen to music or just sleep and i was like.
Dave's Partner
Oh that is so lovely but in retrospect oh my god i can't believe he did that he has earned his right to his twenty minute commute now i'm so happy that we live where we live because he literally drives local roads down to his office it's twenty maybe twenty five minutes in the morning with traffic and at night coming home it's like fifteen minutes it's glorious anyways.
Anna
So we moved out to connecticut for.
Dave's Partner
His job and i don't think i'd ever be here if it wasn't for.
Anna
That and i think the expectation after.
Dave's Partner
Five years is that we must have this big group of friends around us.
Anna
We must be totally entrenched in the community and here's the thing okay so we've moved three times in the last five years so we haven't been in.
Dave's Partner
The same town for longer than like.
Anna
Two years even at a time so that doesn't really bode well for creating strong neighborhood relationships on top of that we're just not out and about that much and i'm sure that will change when we have a kid but other.
Dave's Partner
Than sawyer which has actually led us.
Anna
To meet many people in the area.
Dave's Partner
We'Re just not very socially inclined we're.
Anna
Not members of any social groups we didn't join the country club when we moved to this town and so i don't even really know like how you.
Dave's Partner
Make friends as an adult in the.
Anna
Suburbs it's like when we go out.
Dave's Partner
To dinner at night like everybody else.
Anna
Is just couples going out to dinner.
Dave's Partner
With their friends and no one's like.
Anna
Looking to make new friends and i think all of this sounds depressing but in practice it's actually really freeing because there's something just so relaxing about getting to the weekend and having absolutely no social obligations and again that will change once we have children but right now we really enjoy just getting to a.
Dave's Partner
Friday and a saturday night and just.
Anna
Being able to go to dinner when.
Dave's Partner
We want to go to dinner come home when we want to come home our only restraint is we have to give sawyer her seizure medication at ten pm but guys this is the suburbs like we're back by nine thirty at the latest and that's including getting ice cream after dinner okay so i am.
Anna
A huge fan of the five pm.
Dave's Partner
Dinner at this crotchety stage of my.
Anna
Life because the way i see it dinner is awesome but dinner is is.
Dave's Partner
The pregame to the rest of the.
Anna
Night like i want to have an.
Dave's Partner
Amazing dinner just like in college how i wanted to have an amazing pregame.
Anna
And you know how sometimes like the.
Dave's Partner
Pregame'S almost more fun than the party.
Anna
Because it's the anticipation of the rest of the party and how fun it's going to be well that's how i look at dinner on a friday and a saturday night like i want it to be the beginning i don't want it to be the end and what is the actual party then if dinner is the pregame well the after party.
Dave's Partner
Is usually coming home and watching dateline with dave on the couch and hanging.
Anna
Out with the dog truly like when i think about a weekend and what's.
Dave's Partner
Relaxing to me i don't think about.
Anna
Jet setting off to wherever a flight.
Dave's Partner
Will take us or you know a long car ride to go hiking in the mountains i literally think about rotting.
Anna
On my couch and that's exactly what we do and i was in the.
Dave's Partner
City two weeks ago and dave was in seattle so he was gone for the night and my event for work wrapped up around six thirty or seven.
Anna
So i decided to go get dinner by myself which was something that i love to do towards the end of my twenties before i met dave i just really got used to eating alone mostly because i just figured well why do i have to wait for a.
Dave's Partner
Date to go out to a nice restaurant like i can afford to take.
Anna
Myself out somewhere nice just because i.
Dave's Partner
Don'T have somebody to spend split a meal with on a friday night doesn't mean i shouldn't also enjoy an eight.
Anna
Course omakase and honestly you enjoy food.
Dave's Partner
More when you're alone than when you're on a date in a new relationship now i eat the same when i'm with dave and when i'm alone i mean guys we've been together for seven.
Anna
Years but in the beginning you know when you're just dating and you're almost like not hungry it's not even that you're trying to be cute sometimes you're literally just like nervous or you're excited or you're so focused on the person in front of and trying to get to know them and it's also great like it doesn't have to be a bad thing it doesn't have to be a bad date but your focus is not on the food so you could be at a michelin starred restaurant and.
Dave's Partner
Not want to eat that much or.
Anna
Come out of those dates at least.
Dave's Partner
For me i came out of so.
Anna
Many of those dates with men i dated being like what the hell did i eat i don't even remember like i think it was good but again your energy is somewhere else so short of a long term relationship where you.
Dave's Partner
Can actually you know focus the energy.
Anna
Back on the food going out to eat alone is the best way to actually enjoy fine dining in my opinion and once you get over the like.
Dave's Partner
Slight awkwardness of eating alone like maybe.
Anna
The first ten minutes in you realize.
Dave's Partner
Like nobody gives a about you seriously.
Anna
Especially if you live in a big city like no one's looking at you being like who's that loser everyone's way too consumed with themselves and i think if you learn how to eat alone and just start doing it like there's.
Dave's Partner
No way to ease into it you literally just go to a restaurant that you want to go to alone and you ask for a table for one or you ask to be seated at.
Anna
The bar personally for any restaurant that's not sushi i actually like to sit at a table alone i just think there's more space like i don't really love the bar scene i think it's like almost too social for me like when i'm going out to eat alone like i'm actually trying to go fully hermit i'm not trying to meet people like i just want to eat the food and i guess in the back.
Dave's Partner
Of my mind in my twenties i was always like living my best sex in the city fantasy being like oh.
Anna
You know maybe if i sit alone.
Dave's Partner
At a table for two like the guy sitting next to me will also.
Anna
Be alone and we'll end up talking.
Dave's Partner
And striking up a conversation and ultimately he'll end up being my husband because we realize we're both single and we're.
Anna
Meant for each other long story short that didn't happen in case you missed it i met dave on bumble end.
Dave's Partner
Of story our first date was off.
Anna
Of a dating app so no meet cute there but i hold out the.
Dave's Partner
Flame of possibility for you guys if you learn how to dine alone maybe.
Anna
You'Ll meet a guy because guess what i actually did meet a guy sitting.
Dave's Partner
Alone at dinner when i went out to eat by myself the other night.
Anna
Now don't worry i do not cheat.
Dave's Partner
On my husband but i think the irony of all of this is i spent my twenties fantasizing of how romantic it would be if i was in like my own nora ephron movie and you know meeting somebody in a restaurant when i was going out to eat alone but also simultaneously kind of not wanting anybody to talk to me because i really just wanted to be into.
Anna
The food you know what i remain.
Dave's Partner
Open to all possibilities and either way i was going to enjoy it right but the former never happened to me i never met a guy going out.
Anna
To eat alone however so the other.
Dave's Partner
Night dave's in seattle for work i'm.
Anna
In the city i'm like i'm going.
Dave's Partner
To go out to dinner alone so i went to the sushi counter i.
Anna
Sat down and when i sat down i was like the only person at.
Dave's Partner
The sushi counter there were like four.
Anna
Seats to the right of me like.
Dave's Partner
Three seats to the right of me or to the left of me and.
Anna
It was great i was like oh my god i have so much space like the sushi counter is sort of.
Dave's Partner
An anti social experience for a bar.
Anna
Experience too so if you're looking to.
Dave's Partner
Eat alone but at a bar not at a table a sushi counter is great because like no one expects you to talk to them at a sushi counter like there's no bartender like making conversation with you it's just the sushi chefs doing their thing behind the glass.
Anna
So i sit down and i'm like.
Dave's Partner
Cool this will be great i know how this goes and then all of a sudden the server brings this couple over and they sit her and this guy right next to me and like.
Anna
Literally so close to me that i'm basically in their date because way this bar was set up they were all individual seats but they were like clustered in twos so it was like two.
Dave's Partner
Seats closer together then a space then two seats closer together then a a space and two seats closer together so.
Anna
That the intention was like oh if.
Dave's Partner
You came with another person as most.
Anna
People do for dinner you could sit.
Dave's Partner
With your person with like a sliver.
Anna
Of privacy maybe so they sat this.
Dave's Partner
Couple right next to me but that sliver of privacy was truly just not enough for me and so i waited for like a non awkward moment to slide over to make sure there was like a seat in between me and this couple and the reason why it.
Anna
Was also kind of awkward was because i could tell they were on a very early date i didn't didn't know which date it was like it clearly.
Dave's Partner
Wasn'T the first date but i was.
Anna
Like i just don't need to be a part of this like i don't.
Dave's Partner
Need to be eavesdropping on their whole conversation because where i was sat i was basically like forced to listen to their entire conversation so i moved over seat and i was like cool i'm.
Anna
Good and then another couple comes to.
Dave's Partner
The left and they see that couple.
Anna
To the left of me but that was slightly better because this couple had.
Dave's Partner
Clearly been married or together for a very long time and barely talk to.
Anna
Each other i don't even know if they liked each other honestly but it made me feel less awkward than sitting.
Dave's Partner
In on somebody's very very early date.
Anna
So now there's one seat next to me like solidly next to me and and i'm like okay cool they're not.
Dave's Partner
Going to see anybody next to me.
Anna
Right of course they did because it's.
Dave's Partner
A thursday night and i'm in soho.
Anna
And it's hopping and they seed a.
Dave's Partner
Single man next to me and i.
Anna
Was like are you fudgeing kidding me like this is insane it couldn't have been a woman like it had to be a man but then i caught.
Dave's Partner
A peep of his left ring finger.
Anna
And and saw the ring and i.
Dave's Partner
Breathed a massive sigh of relief and.
Anna
I was like oh great he's married.
Dave's Partner
He is probably out for work or here for work or his wife's out i am here because my husband's out.
Anna
Of town all good this will be a very benign night and it actually was and what also made it better was maybe i'm reading too much into it but i could also tell that maybe he felt a little bit uncomfortable.
Dave's Partner
Being seated next to a random woman at dinner when he was clearly just trying to go out out and get a bite to eat by himself after work on a random weekday while he's.
Anna
Traveling for work and that made me feel a little bit better because it was like this shared awkwardness also the fact that the servers did not tell.
Dave's Partner
The bus boys who brought out our individual meals that we were not together.
Anna
So they kept putting like my order.
Dave's Partner
In between the two of us assuming that like we were there together and sharing the sushi so i kept every.
Anna
Time they brought out like my entree or my appetizer i would have to.
Dave's Partner
Like shift the plate back towards me and he would have to do the.
Anna
Same for his and then i don't know how this couple who was on.
Dave's Partner
A very early date started talking to.
Anna
Us but i think the woman asked.
Dave's Partner
Brad i hope his name is brad.
Anna
I don't know why i have that in my head i think his name was brad the the woman on the.
Dave's Partner
Very early date asked brad if he.
Anna
Was french and he said no and then we all started talking and she was like how long have you guys been together and we were like we're not together and she's like oh because.
Dave's Partner
You'Re both wearing rings i was like yeah that's just a massive misunderstanding and.
Anna
Coincidence so then we start talking to her and the guy she's with and.
Dave's Partner
It turns out they're on their second date and it's going really well and we all have a laugh and we're talking about how boston is kind of a second tier city to new york.
Anna
Sorry guys if you live in boston.
Dave's Partner
And you love it it's just not my favorite city my husband's from boston.
Anna
It'S such a cute city but like.
Dave's Partner
In comparison to new york i'm like.
Anna
No dice so anyways the night goes on i probably spend in total an.
Dave's Partner
Hour an hour and fifteen minutes there at the bar eating dinner talking to all these strangers and it was just like a really good time and then brad left and i left and i went home and you know nobody exchanged numbers or anything like that nobody vowed to stay in touch and it was.
Anna
Just a very new york inter interaction and it was a funny story because.
Dave's Partner
I called dave on the way home.
Anna
And i was like oh my gosh.
Dave's Partner
Like i met this totally random dude who sat next to me and it was awkward because everybody kept thinking we were together which i guess is logical and then we met this couple who was on a very early date and.
Anna
At the end of it this is the moral of the story of my very long winded explanation of a random.
Dave's Partner
Night out in new york city but.
Anna
I was driving home from the city.
Dave's Partner
It was late and and after i hung up with dave because he had to go to bed and wake up really early in the morning i was.
Anna
Like i just had a very very social night like way more social than.
Dave's Partner
I ever thought it was going to.
Anna
Be like i thought it was going.
Dave's Partner
Out to dinner alone and just eating.
Anna
Some good sushi and i ended up talking to three really pleasant people like they were great couldn't have asked for.
Dave's Partner
More entertaining people to be sat next.
Anna
To at the sushi counter but i remember feeling this feeling that i hadn't felt in a really long time and it was this feeling of i very alone even though i was more surrounded.
Dave's Partner
By people than i ever thought i would be over the last two hours.
Anna
And i think that's when i realized like my definition of community is no longer the amount of people i have around me it's who i have around me and that who has become a.
Dave's Partner
Very very small circle of people it's really my husband my parents my dog at its core and then a few.
Anna
Scattered friends in connecticut that i've made none of whom really know each other over the last five years my girlfriends.
Dave's Partner
From back home some of whom still live back home some of whom live.
Anna
In the city and we don't see.
Dave's Partner
Each other that much but we do keep the group chat very alive and.
Anna
Well which i'm very grateful for and a few friends from my twenties and that's basically it that weird feeling of.
Dave's Partner
Being incredibly social but feeling so lonely after was something that i only experienced while living in new york because i.
Anna
Had so many friends and i was so good at making connections with random people and at the end of the.
Dave's Partner
Night i would go home and i.
Anna
Would feel so alone because a lot of those friends that i used to.
Dave's Partner
Party with i don't talk to anymore.
Anna
And it's not that they were bad people it's just we never had more.
Dave's Partner
Than a surf surface level connection and.
Anna
I think that's definitely what has kept dave and i from wanting to have.
Dave's Partner
A bigger circle of friends in connecticut from wanting to join the country club i mean for various reasons we're not.
Anna
Exactly country club people but that is.
Dave's Partner
A good way to meet people if you join the social or the country.
Anna
Club in your area and we just haven't done that because i don't actually think it's possible to have really close relationships with thirty couples it's just not like i have a hard time keeping.
Dave's Partner
Up with the five friends that i do see on a regular basis and beyond that maybe the eight friends i see once a quarter or once a.
Anna
Year and i don't get enough time to see those people and so i think as you get older you just realize that you need so much less and that's actually a lot more freeing than when you're in your twenties and.
Dave's Partner
Your whole identity is based on having.
Anna
This big group of friends and people you can post pictures with when you're out and show everyone else that you're with this big group of friends like these days if someone were to take a photo of most of my friday nights it would look pretty sad it's.
Dave's Partner
Just me dave and sawyer on the.
Anna
Couch watching a story of how somebody.
Dave's Partner
Inevitably murdered their wife or their husband by poisoning them and that's it and.
Anna
It'S not much to show for but it's what makes me feel community and.
Dave's Partner
It'S what makes me feel home and.
Anna
I think that's what i would hope for all of you i think it's.
Dave's Partner
So crushing when we obviously go through.
Anna
Normal breakups with romantic partners but it's even harder to reconcile with like the.
Dave's Partner
Slow ebb of a friendship and how a lot of times from our twenties into our thirties a lot of friendships.
Anna
Just fade they don't necessarily break up there's no defining breakup point but they just fade and ultimately you realize that the ones that faded were probably not.
Dave's Partner
Meant to be in your life forever.
Anna
They were only meant to be part of your community for a really short amount of time and at this stage like i've realized the people i've kept in my life my friends and the.
Dave's Partner
Ones who've kept me in their lives you know i'm their friend too and it's a very two way mutually beneficial.
Anna
Street are the ones that are not.
Dave's Partner
Just catch up friends they're the friends that want to break it down with.
Anna
You and i mentioned this in a.
Dave's Partner
Video a few months ago but like.
Anna
These are the only friends that i.
Dave's Partner
Really feel connected to at this point.
Anna
In my life like of course there.
Dave's Partner
Are people that i see where all we basically do is regurgitate the last six months to a year of what.
Anna
Happened to us but i don't end.
Dave's Partner
Up leaving those conversations and those dinners feeling like my cup it runneth over.
Anna
So to speak it always feels like.
Dave's Partner
A little bit more of a chore.
Anna
Maybe that's a little bit harsh it always just feels like with friends who you just simply catch up and you.
Dave's Partner
Don'T dissect the happenings of your life.
Anna
Where it just feels like a little bit transactional like we were friends at one point maybe and maybe at one.
Dave's Partner
Point we were break it down friends but we're no longer that and we're trying to hold on to what we.
Anna
Had in the past even though we're.
Dave's Partner
Really not a part of each other's.
Anna
Lives anymore and i think it's time.
Dave's Partner
For all of us at whatever stage.
Anna
Of life you're in i'm in to let go of those friendships not because.
Dave's Partner
Those people are bad or because i'm bad or because we're bad friends to.
Anna
Each other it's just because life takes you in different directions and it doesn't.
Dave's Partner
Negate how strong the friendship was at.
Anna
Some point it just means it's time to move on and so as we come upon this cuffing cold holiday season where this idea of gathering is all around us i really urge you to really think about who your actual community is like who can you actually not live without in your life and focus on those relationships instead of focusing on.
Dave's Partner
Maybe somebody's opinion in the periphery that.
Anna
Doesn'T really matter because we allow those.
Dave's Partner
Periphery people to affect us way more than we should and at the end.
Anna
Of the day if you even have five people people you can count on.
Dave's Partner
One hand that you can say these are my ride or die humans it can be family friends a spouse a significant other your dog or your cat.
Anna
I don't care if you have five living sentient beings that you can go.
Dave's Partner
To in your life that you know are there for you you're a lucky.
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Ai had the time of my life hey i never felt this way before.
From building timelines to assigning the right people and even spotting risks across dozens of projects monday sidekick knows your business thinks ahead and takes action one click on the star and consider it done.
And i owe it all to you.
Try monday sidekick ai you'll love to use on monday dot com.
Host: Anna Kai
Date: October 3, 2025
In this candid, relatable episode, Anna Kai unpacks the emotional nuances of dining alone and how her definition of community has transformed over time. Blending humor, vulnerability, and real-life stories, Anna explores loneliness versus solitude, how our social circles evolve, and why it’s freeing to let go of outdated social expectations. She reflects on moving, adult friendship struggles, and accidental social moments—always with her signature “no bullsh*t” honesty.
Anna’s style remains unfiltered, funny, and deeply honest—peppered with self-deprecating asides and relatable admissions. She moves deftly from humorous observations about seating at sushi bars to heartfelt reflections on the pain (and relief) of outgrowing old friendships.
This episode is a refreshingly honest look at how community, friendship, and the solo experience shift as we grow older. Anna’s real-life stories and “too honest” insights will resonate with anyone who’s ever felt “too much or not enough.” If you’ve wondered why surface-level socializing often feels hollow, or pondered how to enjoy your own company, this episode offers comfort and validation—no toxic positivity, just the brutally honest truth.
Summary by Podcast Summarizer AI