Excuse My Grandma
Please Excuse My Grandma While We Get Brutally Honest About Love With Anna Kai
Thu, 23 Jan 2025
In this episode of Excuse My Grandma, Kim and Grandma Gail get brutally honest with special guest Anna Kai, aka @maybeboth. They escaped bitter cold New York to enjoy new restaurants in Palm Beach, see friends, and work, of course. Social media star and podcast host Anna Kai joins Excuse My Grandma to share her honest thoughts on looking for a husband, “committee decision dating”, grief, and being an influencer. Anna tells Kim and Grandma Gail about her attempts at becoming a blogger during the pandemic instead of getting a ‘normal’ job. In The Grandma Report, the three women discuss dating trends found by Tinder in a recent article. Whether looking for a man in finance or asking friends to vet a guy before the first date, Anna shares her personal experiences based on the study. They then read an email from Grandma Gail’s Hotline, where a listener receives much needed tough love. Want Gail’s honest opinion on your dating dilemma or family drama? Email [email protected] or DM us on Instagram with your voicemails! Kim, Gail, and Anna then play their new game “Should We Bring It Back?”, questioning whether or not old dating trends like ‘Guy picks up the girl for the date’ and ‘meeting the parents at the door’ should be modern traditions. Anna, who lived with her boyfriend and parents under one roof, had a lot to say about these. To finish the episode, they play Grandma’s Old-Fashioned Dating Quiz. The results? Grandma approved! Anna also shares inspiring advice from her own grandfather, including embracing being alone and moving forward by taking risks. Grandma Gail then imparts her words of wisdom, telling Anna, Kim, and listeners to live everyday, how to deal with loss, and remember the good things. Follow us on Instagram @excusemygrandma TikTok @excusemygrandma Watch on YouTube Spotify Music By: Guy Kelly (00:00) Introduction (02:38) Interview with Anna Kai (26:26) The Grandma Report (34:33) Grandma Gail’s Hotline (38:30) Should We Bring It Back? (41:49) Grandparent’s Advice (49:30) Grandma Gail’s Old-Fashioned Dating Quiz
Chapter 1: What have Kim and Grandma Gail been up to in Florida?
Welcome back to Excuse My Grandma. It's Kim and my co-host, Grandma Gail. Grandma, let's update everyone what we've been up to.
Well, we basically got out of the cold weather the month of December.
This is peak snowbird time.
Exactly. So it's been nice and January is good so far.
no major storms so we're good to go yeah it's so much easier to get content down here well it's easier because i'm living with you and there's no commuting or whatever but it's harder because we're in florida and it's more distracting and like yesterday you got mad because we were supposed to or you thought we were supposed to do videos together but i went on a walk with my friend yeah well that was a bit much i waited for like three hours that was the longest walk in history i
I don't remember making that plan to do videos.
Whatever. I watched something on Amazon.
Maybe you wanted to watch something that was your excuse.
Probably.
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Chapter 2: Who is Anna Kai and what does she do?
A lot of new restaurants are opening, which is exciting. Yes. A couple of places in West Palm. Yes. that have been quite nice and we'll tell you about them as the season goes on because we've only tried them once, so we're not 100% sure. But I'm really excited because it brings a little different flavor when you get some variety.
And we have exciting guests the next few months, all coming into our Palm Beach little studio. And today we want to tell you about our guest, Anna Kai, who's maybe both on social media. I have seen her stuff for a while, actually, and grandma is new to her. Every time we have a guest on, I'm like, this is who it is. And I show all the videos and then we get grandma hooked, too.
But she's a lifestyle content creator and host of the podcast Brutally Anna. And she has these witty takes on modern dating, on relationships, on being a woman, on any sort of advice. And she does it usually when she's getting ready, doing her makeup, doing skin care. So we're excited to talk to Anna today. I can't wait to meet her, Kim. Hey guys, we are joined by Anna Kai.
Anna, welcome to Excuse My Grandma.
Thank you so much for having me. I'm so excited to be here in sunny Florida.
I know. We're happy you got to be here.
The option between New York and Florida was like 100% Florida in December.
Yeah. From Connecticut, how long is it to get to the city?
I mean, it should take an hour and 15. No way. No way. No way.
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Chapter 3: How did Anna start her journey in social media and dating advice?
I'll name you. It's coming. It's storming all over the place.
We need a Graham McGill weather report. Well, I watch that constantly. Can we? We should do that.
Well, it's storming. Yeah, we'll have to do this. I have a degree in television watching the weather. Right. Right. I don't actually, I'm not a meteorologist.
Yeah, yeah, yeah. I was about to find out something new about you. I'm working on that. Okay. And obviously you have over a million followers. You have a successful podcast. But for those who don't know you, how did you get started with social media?
I just thought I wanted to do it. And I was having kind of a quarter life crisis. I was in my late 20s and then COVID hit and I turned 30 in the middle of a pandemic and I was unemployed. And I think most people would have just been like, all right, I will restart, get a new job. And I was like, instead of getting a normal job, I am going to start a blog.
So my millennial ass started a WordPress when everybody was getting on TikTok at the time. Cause you know, 2020 during the pandemic is what we do. Exactly. So I just refuse to adopt new technology. This is why I belong like in Florida. I just want to like live here and be like, Yeah, but like very, very, I'm so bad with technology for how old I am.
People are like, how do you not know how to do this? Like, I don't. And so I was like, I'll start a WordPress. I'll start an Instagram. And I tried to do home decor at first and it didn't really work out. And then I switched to fashion. And I actually did Instagram for two years before I made a TikTok very unsuccessfully. And then I created a TikTok that didn't go well for a while.
And I just decided to pivot. Instead of doing fashion content, I was like, let me upload a video talking about dating and relationships, and it went viral, and I was like, oh, this is what I should be doing. So yeah. You're our competition.
Well, it's a little different, obviously, because our experiences are different. Our age range are different for every reason. But you're such a good storyteller, because even when you're doing, it's enthralling. Like, I've never, obviously, I've seen your videos before. We set this up and everything. And I've never swiped without finishing a video, which is really hard as a creator to do.
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Chapter 4: What are Anna's thoughts on modern dating trends?
I dated a lot of men in my 20s, and I was always looking for my husband. I think a lot of women in their early 20s just want to be single for a while and have fun and date casually. And that was just never me. I would have been fine meeting my husband freshman year of college.
I went to NYU.
Like us. Like me. Yeah. I mean, I was like always just looking for my husband. And I think as a result, I just ended up getting into a lot of interesting situations with men that I probably shouldn't have been dating very long term. And I had shit to say, quite frankly, about it. And I was like, this is a topic that I can expound upon.
Because I think especially for women in their 20s in a major city, dating is just such a slog. Because it just takes such a toll on your self-confidence and just kind of your emotions. And I don't think it's quite the same for straight men anymore.
And I think that's just social conditioning and what women are taught, that our value lies, and especially us as millennials, our value lies in who wants us, right? And my husband was single for four and a half years before we met. He was dating, but he didn't get into any serious relationships. And I was like... did you go to therapy because you were single for four and a half years?
No, men don't think that way. They don't think that way. He's like, my mom started to get a little antsy, you know, but he was like, I just figured when I met the right person, I would settle down. And so I just thought there was something to say there. And I really try to approach my content from an empowerment perspective for women. And look, my my advice is for men, too.
I have a small percentage of male followers who at the end of the day,
dating is just it's such an insane thing because everybody brings their baggage to a relationship and everybody has their stuff you know so i want to ask you something because we've discussed this a million times do you think because millennials have are dating so much they can't make a commitment until almost they're out of their period where they're they're uh they're
really into their 30s because during their 20s they're swiping all the time and they don't think anybody is good enough when i was dating you dated four or five guys your mother said get married you picked one that looked all right on paper you figured he had a good job and you got married and i was listening to um what's the fellow who's um on um you know the program that uh mr wonderful
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Chapter 5: How did Anna meet her husband and what was their dating experience like?
Yeah, and it's like you just don't... You can't be one foot in, one foot out. And I think if one person or both people are, that's just not the right person. It just has to be easy.
I really believe that at the end of the day, like if you're coming to me, which I love my community, but if you're coming to me, a random ass person on the Internet who's unqualified, who's never gone to school to be a therapist or anything for advice. on what to do with a man, it's most likely because you already know that relationship is somewhat over.
And you're just trying to figure out if there's any way to save it. Right.
It's so true. I remember like in other past relationships, like watching tarot card readers on my TikTok being like, this message is for you. Five million people are seeing that. And I'm like, oh, my God, I have to follow every advice because you're like seeking for any sort of.
answer but i think you're right when you're like really confused unless it's actually a big thing you want advice for and then you go to family or friends probably um i i feel like it's more knowing that like this isn't the right thing as you're saying
yeah and i think that was with my husband how long did you go out before we were only together for a few months before we made it official okay and it wasn't even like men are just so dense sometimes like i had a rule for myself that i would not get physically intimate with a guy until he was my boyfriend i was his girlfriend you were going to introduce me to people and that's kind of old school i know but i just knew that is not something i am interested i'm not interested
in casual sex right and you know a lot of women can have casual sex and not get emotionally attached that was never me again always looking for my husband trying to make every wrong man my husband and so I think it just wasn't a conversation at first and he was always just like and then it got to a point where we'd been dating for three or four months and he was like I what's going on with you?
I think he thought I was like super religious or like maybe I was a virgin or something like that. I was like, no, here's my role. And if you are not there yet, that's fine. I'm happy to continue seeing you. We just can't be physically intimate. And he was like, oh, that's it. He was like, I just assumed we were already dating and boyfriend girlfriend.
I was like, no, you have to have the conversation. Right. So that's kind of how it came about. So he always likes to joke. He's like, you asked me to be your boyfriend. I was like, I did not ask you to, you know. I think that's kind of where it started. So it was very easy. It was very organic. We were together for four years before we got married.
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Chapter 6: What advice does Grandma Gail have about love and loss?
Yeah, I guess actually that's true, but not late. Like, 8 or 9.
Oh, that's not really... Well, since we now... Since COVID... Dinner's gotten earlier and earlier. Even up north, even in the north when we're out for dinner. We used to go out at 7.30, 7.45. No, no, no. Here, everybody wants to eat by quarter of seven. I'm home by 8.30. I have to put on my Amazon or Netflix. I mean, my night is finished at 8.30, quarter of nine. I know.
So let's get back to your podcast. Enough with this place.
I wanted to ask what you, like what you said earlier kind of interested me in that like always looking for my husband mentality. Do you think looking back you should have shifted your mindset on that or are you like that's how you were and you're glad that's the way you were thinking?
Because I feel like
that's how she was brought up well that's how my mom and dad brought you up well no actually my parents are very progressive in the sense that they were never like you need to get married right away or anything like that for me what that really came from was i chose a very unconventional path out of college you know i got my bachelor's degree at nyu and i knew i wanted to go into entertainment and media so i came out of college and i was trying to be an actress
And at the time I was doing a lot of gig work. I've done lots of random jobs to supplement my income. And I think my desire to find a husband was not so much the fact that like I needed to get married, but I desperately was searching for stability. And I did not have that in my career. So I was like, if a man can give that to me, that would be great. And it's not... That's not good.
No, it's not great. That's not good. Grandma's saying that's not good. Exactly.
Do not do that. So do as I say, not as I did. And I had to learn the hard way that that's not how you actually find the love of your life. It's not a coincidence that by the time I met Dave, I was 27, almost 28.
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Chapter 7: What insights did Tinder provide about dating trends?
And that has to do very much in the real estate trade, especially in Manhattan.
I was good at it, which was for the first time. I mean, imagine going through your 20s, sucking at every job that pays you any amount of money, right? It was just a very demoralizing time in my life because I was a good student. I always did the right thing, but because I had this crazy dream, I then spent the rest of my 20s feeling like I was just a failure. So I was good at real estate.
I was finally earning a really great living. I had disposable income. And by the time I went on my date, my first date with my husband, I was like, I would love a boyfriend right now, but I don't need to invite chaos into my life. So if this isn't it, that's okay. And that's when it happens. That's when it happens. Exactly.
You hear that a lot. Yeah.
Yeah. Because I think, unfortunately, you know, your path and Kimmy's path were very similar in the sense graduating from very good schools.
kimmy always wanted to be in some media fashion she went to work for a radio for a television uh station and then during coven they closed so then what but i feel like for to get successful in social media you kind of have to have a similar mindset or like entrepreneurial spirit that we do because yeah we're creative and like the channel it came out of may have not been acting to start with.
It still maybe could be one day. I don't know what your aspirations are, but I feel like you found what worked and got you that audience and hopefully that outlet for creativity. Exactly.
Creativity and making money. The thing is, I think that's what people who listen to all of us don't realize. We are making a living from this, a very good living, which probably would not have happened in the regular workplace. even my age, you know, this is what's selling products. You know, people say to me, oh, really? I said, yes. Who do you think is buying off of your phone?
It's we're advertising and you're buying. So it is a business and a big business today and becoming even more so. The more I read, the more I see people going to less do, less advertising, and certainly in newspapers, forget that, but in magazines, they are this big. They're as big as nothing. and they're really focusing on influencers like you.
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