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When did making plans get this complicated? It's time to streamline with WhatsApp, the secure messaging app that brings the whole group together. Use polls to settle dinner plans. Send event invites and pin messages so no one forgets. Mom 60th and never miss a meme or milestone. All protected with end to end encryption. It's time for WhatsApp message privately with everyone. Learn more@WhatsApp.com so good, so good, so good. New markdowns are on at your Nordstrom Rack store. Save even more. Up to 70% on dresses, tops, boots and handbags to give and get. Cause I always find something amazing. Just so many good brands. I get an extra 5% off with my Nordstrom credit card Total queen treatment. Join the Nordy Club at Nordstrom Rack to unlock our best deals. Big gifts, big perks. That's why you rack. There was a time in my 20s when I had no idea when my period would come. That was actually basically my entire 20s. It wasn't like, oh, I was sexually active and hopefully I'm not pregnant. It was just like, no, I just never tracked my period because I always assumed it would come and it always kind of did. I've been lucky enough to be pretty regular and throughout my womanhood, and so I never had to think about it. And it was only until recently that I started using Flow, that tracking app, to track my period. And the only reason I did that, by the way, was because in the last few years, I've developed a horrible case of PMDD. And I started noticing that every month, the 10 days before my period, I would feel horrible. And then the day my period would come, I would feel reborn. And I was like, what is this? And so then I started realizing, oh, maybe I'm not just a sad person on a monthly timed schedule. Maybe it's my hormones, which, that's fun. So with the help of my lovely psychiatrist, I developed a plan to go on Zoloft. And I felt great for a while and then I started gaining weight and that made me feel not great. So I went off of it. I went on Wellbutrin, and that didn't really help. Got off of Wellbutrin, tried to raw dog it for a little bit, then went back on Zoloft and just said, fuck it, I don't care if I'm 10 pounds heavier than I typically am. I just want to be happy again. And it worked for a while. But then the problem was I felt like I had to keep upping my dosage. Like, it would work Great. For a month and a half, two months, and then I would start feeling shitty again. So we would go up by 25 milligrams and. And I would feel a little bit better again. And I don't know if that's just placebo effect, but then the cycle would repeat itself. And then we decided we wanted to try for a baby, because why not throw a kid into all of this mess? No, I swear I'm a lot more mentally stable than I appear. I'm just. You know what? This is a podcast and I'm speaking into the void right now, so I'm dramatizing this for effect. But I do want you guys to know, especially those of you who've been following my pregnancy journey, or lack thereof, on social media, that this was a very well thought out decision that Dave and I came to after three years of marriage to try to have a child. But going off of Zoloft again was partly due to the fact that I was like, okay, if I'm gonna try to have a kid in my body, right? Because, like, I know Dave and I are doing this together, but, guys, like, I'm not one of those people that it's like, oh, we're pregnant. No, no, no, no. I'm like, it's always been so weird to me when couples, especially the men, say we're pregnant. It's like, bro, unless you're carrying half of the child, you're not pregnant. Your wife's pregnant, you had sex, had a really great time, and now you get to wash your hands of this for the next nine months, Albeit, yes, you have to deal with our hormones and our cravings or whatever, but try carrying a kid for nine months, okay? Like, I would take going out at 2am to pick up mango sticky rice ice cream from CVS any day, than having to deal with the hormonal crap that pregnancy, motherhood, just being a woman in general entails. But I digress back to the point. I went off of Zoloft because I felt like it wasn't working as well, and I didn't want to have to up my dosage continuously while I was pregnant. And so I was like, you know what? Let me just try going off of it for a few months before we start actually trying and see how it goes. And I don't know if it's like the stars aligning or just where I was in my life, but I actually felt pretty fucking good. And I felt pretty fucking good because instead of using Zoloft as the only crutch in My life defend against depression and anxiety. I decided to implement healthier changes in my life that I probably should have done all along, like eating breakfast, working out more regularly, just being nicer to myself, which that part I'm still working on. But you know what? We're all a work in progress. So I did all of these things, and I started taking prenatals and multivitamins, and I finally listened to my doctor when she said I had a vitamin D deficiency. I was like, okay, now I'm going to start taking vitamin D. Because you know what? Honestly, sometimes you just need the thought of being responsible for somebody else to be responsible for yourself. I know that's messed up, but I have been severely lacking in vitamin D, as many of us are in the northeast for my whole entire adult life. And every year, I get my blood work done, and every year, my primary doctor is just like, you need to take vitamin D supplements. And I'm like, sure, I will think about that. And then I never do. And it turns out all that stuff helps. It is not a magic bullet. I've certainly had very down moments between the time I started this health journey, if you want to call it that, and now. But overall, I got myself to a point, like two to three months in, where I was like, you know what? I'm good. We can try doing this. I am never gonna be more ready, because for the longest time after we got married, it was like, well, I'm trying to build my career. I'm trying to get us to a stable place. And, you know, I wasn't doing it alone. But it's not just about what Dave's career is doing. It's about also what my career is doing. And I felt very strongly that I wanted to get established enough, or at least just feel grounded enough that I could take a step back without feeling like I was gonna lose it all. Also really wanted to move and be in our forever house before we had a kid. And I know, again, that these are all the ideal circumstances, and plenty of people have children under less than ideal circumstances. But, alas, I am a ninny, and I am a delicate flower. I am Sawyer, our dog, who is allergic to everything and needs the most perfect, ideal conditions to just survive. That's me, okay? I'm just not superwoman when it comes to having kids. I know there are women who have kids on their own, who work five jobs, who go to the gym, who. I don't know, basket weave. Like, that's just not me. I needed to focus on one thing At a time. And for the last three years, that's been my career. And I finally got to a point where I was like, I think I'm ready. And you know what the best part about being married to Dave is? He has always let me know that it is actually my decision as to when I'll be ready to have children. And not because he's like, well, I don't really care. Like, I'm ready and I absolve myself of this responsibility. It's just that he's fully aware of how much of a physical and mental toll it's going to take on me, comparably to the physical and mental toll it's going to take on him. And look, having a child is a collaborative experience in many senses of the word. But I just have to say I feel very lucky in the fact that he wasn't like, well, you know what? We're never going to be more ready because he could have said that last year. He, you know, we were not in a vastly different situation other than the fact that we were in the process of moving. He could have said, you know what? We need to start trying right away. Like, he had turned 40 last year, which feels like kind of a monumental number for men. And he could have pressured me and maybe I would have caved. Probably not. I mean, if you guys know me, I probably just would have punched him. So it really wouldn't have done anything. But all I can say is I am really glad he did not put any pressure on me. Over the last three years of our marriage, or really over the last seven years we've been together as to explicitly state when I'll be ready to have a child. So that time is now. And I guess what we're going to talk about today is how much of a fucking bitch it is to try to get pregnant. Because you spend your entire 20s avoiding getting pregnant, just praying that the stupid you did on a Friday is not going to haunt you the next week when your period is supposedly going to come. By the way, in my 20s, I always thought my period was like 30 days apart. I don't know why. I just assumed that was the case. And every month, if it was late, sometimes it would come early, Sometimes It'd be like 20 days in. I'd be like, oh, great, I'm not pregnant. But sometimes it would be like 35 days in and I'd be like, freaking out the last five days. And it's actually crazy because now that I know all the science behind your hormones and getting pregnant, like, if I was that late, I should have gone and just taken a pregnancy test because it would have told me right away. It tells you pretty much the day after your missed period if you're pregnant. These very simple plastic tests that are actually quite expensive for good reason, I guess, because the technology is actually really freaking accurate. So. So all these things I wish I knew. But you know what? It was in my 20s, too. I never went to get a pregnancy test when my period was a little late and just late within the natural span of a woman's cycle. Because I think it could be, like, anywhere between, I don't know, 28 and 35 days is typical. But anytime I was late, I was like, I'm not going to take a pregnancy test because if I don't take a pregnancy test, that means I'm not pregnant. Because ignorance was bliss, and I chose to remain ignorant. And it worked out. Look, I never got pregnant out of wedlock unintentionally, and I was stupid in my 20s. What can I say? Had some boyfriends, had some dudes I hooked up with that were not my boyfriends. But we had fun. We came out of it unscathed. And alas, I urge you all to stay safe, get tested for STDs and use a condom. All right, there's my PSA for the day. I feel like I need to say that to anybody who's listening and feels like you can play with fire and not get burned. Sometimes that's the case, and other times you get gonorrhea or a baby that you did not want. Neither of which is a good case scenario. But, alas, I am now 35. I have one sexual partner. It's my husband. And the process has been horribly unsexy because it turns out that. That there's really two days out of the month that you can get pregnant and, like, four optimal days to have intercourse. That will optimize your chances of getting pregnant. And I didn't know that. Limu Gameu and Doug, Here we have the Limu emu in its natural habitat, helping people customize their car insurance and save hundreds with Liberty Mutual. Fascinating. It's accompanied by his natural ally, Doug. Uh, Limu is that guy with the binoculars watching us. Cut the camera. They see us. Only pay for what you need@libertymutual.com Liberty. Liberty. Liberty. 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Nothing really sticks with anybody until it's relevant to them. And so again, most co EDS at this point are sexually active. Maybe a good time to teach people about their reproductive systems and sex would be like when they're having sex. Like, that would have been great. I would have loved it if somebody just told me at nyu, you know, that fancy school that we paid a lot of money to go to, that I should track my period with an app. That would have been nice and therefore I wouldn't have to freak the fuck out every month wondering if my period was gonna come. But anyways, since no one taught us that, I guess I'm turning this episode into an unofficial sex ed class. Or really how to get pregnant 101. And how somebody who never really dreamed of being a mother but always knew she wanted to be one, that someone is me, found herself in this situation hoping to not get her period for the first time. And it is really disappointing when you do everything right. You pee on the ovulation sticks. Yes. You can go buy these sticks that you. You sort of. You can pee on them. But I don't. Okay. Because I find it too difficult to like, catch the test strip on the stick midstream. So what I do is like, I pee into a solo cup, which we have all these solo cups left over from Dave's 40th when we had this like, massive beer po long and this other beer game. I don't know what they were doing. Oh, slap cup, flip cup, slap cup. I don't know. Anyways, a bunch of Dave's friends from high school played a lot of drinking games with these red solo cups that we have so many left over from unused, obviously. And I was like, great, these will be my urine containers for my ovulation strips. And so I I have been using them. And what I'll do is I'll pee into the cup and then I'll dip the test strip into the cup. And that to me just feels more civilized. I don't know, like, I don't really want to accidentally pee on my hand or anything like that. So I just pee into the cup, I dip my clear blue Advanced Digital Ovulation test in for about 15 seconds, as the instructions tell me, and then I put the cap back on the strip that like, hit my urine and then I place it on a flat surface, AKA my bathroom counter. And then I leave. And I come back after 5ish minutes, hoping to see a flashing smiley face or just a solid smiley face, both of which indicate it is time to do the Humpty Dumptys in our bedroom. And so I feel like the amount of people who get accidentally pregnant, it's like, oh my God, you are actually so unlucky. Because first of all, there's two days out of the month where when you have sex, you are likely to get pregnant. But even if you have sex on those two days, there is only a 20% chance that you can get pregnant because it's just that hard. So for the people who like, accidentally get knocked up by their boyfriend in high school and college, it's like, whoa, you are a fertile nymph. Who are you? Oh my gosh, that's insane. And it's like, I wish the world just worked in a way where everybody who wasn't ready to get pregnant just didn't, you know? And all the women in their late 20s, early 30s, mid-30s and beyond trying, trying to get pregnant because they finally built their life up to a point where they're reasonably sure they're not going to just traumatize their child to the best of their ability could get pregnant. But of course, it never really works out like that, right? So I've had so many girlfriends go through these really, really tough fertility programs and journeys because it's just hard. And you don't know until you start trying. And we are going to keep trying naturally for the next couple months before we think about what the alternatives might be. Because that's what my Guido told me. She was like, look, you guys tested everything. Everything is fine. There's no reason you shouldn't be able to have a child naturally. So just keep trying and then we'll reassess at like the 8 month mark if you're not pregnant yet, and that doesn't sound like a long time, but you have to think about timing sex every month for eight months is just insane. Mostly because two, it never comes. Like, you never ovulate at a convenient time. Like, we're always on a plane. Or like, you know, one time Dave had to change his travel schedule for a work thing because I was ovulating and I, like, didn't know until the week of. And I wasn't sure if it was going to be early or late. And so it's just always horribly inconvenient. But alas, this is the journey that we're on. And so, you know, I'm gonna be grateful for it, right? Practice gratitude. But I just wanna say, like, for anybody listening, if you've had a really hard time getting pregnant, I now understand why it sucks so much. I only understood in a very kind of detached way when my friends would talk about their pregnancy journeys. And a lot of them did end up resorting to ivf. And now they have healthy, beautiful children. And so it does work out. And modern science and technology has come a long way so that. But most of the time, even if it's harder or it costs more money, you can have a child, right? But it's just like, I never really quite understood the, like, agony and torture of ovulation cycles or, like, taking your basal body temperature, which, by the way, I haven't done and I just, I refuse to do. For now, I'm just like, you know what? This clear blue digital ovulation test, I'm just gonna wait for the smiley. I'm not doing this body test thing, okay? And don't even get me started about the people that are like, well, just feel your cervical mucus. No, I am not feeling my cervical mucus. I'm not using that to judge. And by the way, I'll probably be wrong anyways. Okay, so just a word to all of my ladies who have tried to get pregnant and it has not been easy. I feel you. I'm in the same boat every day. I want to make a video about how frustrating this all is and, you know, some other things that I'm not really ready to share yet about our fertility journey that hopefully, in hindsight, I will be able to share. But then I realized, like, hey, I'm actually okay with this one bit of my life not being shared online in real time just because I am still processing how I feel about it. And it feels like a safe space on this podcast because there are no trolls, right? Like, it not going to get blasted out to a weird cohort of men or just kind of pick me girls who are like, well, it's your fault for waiting that long. Which, by the way, somebody did say to me when I did talk about our fertility journey. She was like, well, you know, the optimal age is to have a child in your early 20s. And, like, the fact that people say that that's not true is just really, really false. And I'm sorry. I was not ready to have a child when I was 24, no matter what the. My uterus looked like. Okay? I am so glad I waited till this point, even though it sucks right now, But I am so glad because I would never have the life I have now if I didn't wait. I don't know what kind of life I would have. And I don't really know that many people that are like, oh, I regret having my child. Even though I wasn't ready to have my child. I'm sure I wouldn't regret it, but there's a lot of life I would have missed out on, and I'm so glad I lived. Lived that life that I have. So, yeah, not helpful to those people, but it feels safer to talk to you guys about this. And hopefully, you know, I don't know if I've offered any helpful information, but in any case, I hope you feel a little less alone if you are going through this or if you're thinking about going through this or if, you know you're going to have to go through this, because a lot of my girlfriends who have not had regular periods who have pcos, a lot of these issues people know now well in advance of them even having, like, a significant other to procreate with. So I feel like it's this, like, looming topic for a lot of women where they're like, I know I'm gonna have issues having a biological child, and I'm a little bit freaked out about that, but it's not in my present right now. So I'm just gonna keep taking shots of tequila and eating sushi and we'll figure out the rest later. Which, as somebody who is preemptively, by the way, giving up sushi in the hopes that I'm pregnant. Eat all the fucking sashimi you want, okay? Because that is the thing I miss the most. I always think that for my friends, it's not going to be easy to tell if I'm pregnant, because I've been sober for the last two years. But, like, I will probably be weird about going to a sushi restaurant, which anybody who knows me in real life knows that I would Never say no to going to sushi for lunch or dinner. So dead giveaway there. In any case, I just want to say that my girlfriends in real life and those of you online who have told me your stories of how it took you, like a year and a half to have a child, but now you finally have, like, the most beautiful baby. Those are the most inspiring stories, and those are the only stories I really need to hear right now. I don't need any advice. I really, really despise the amount of just absolute bullshit surrounding the topic of getting pregnant. Like, if you tell me to take Mucinex one more time, I'm going to scream. Like, I just can't. I can't listen to it anymore. I don't know if it works, but I'm pretty sure if it did, like, my OBGYN would have told me that by now. Anyways, look, hopefully by the time I check in with you guys again, whether it's on this podcast or on Instagram TikTok or on Substack, I am pregnant and I'm complaining about being bloated. And then we have a whole other set of problems. But as of now, I'm definitely not pregnant. I still get weird cravings, but that just might be me. And we're gonna figure it out and we're gonna have a baby eventually. Because you bet your ass that even though we don't have a child yet, not even a bun in the oven, we have two names picked out. One for a boy and one for a girl. And they are too fucking cute not to ever use.
Host: Anna Kai
Date: October 24, 2025
Anna Kai gets brutally honest about the messy, anxiety-inducing reality of trying to get pregnant in your mid-30s. With signature wit and vulnerability, she unpacks the unexpected emotional and logistical tolls of fertility “math,” the failures of sex education, shifting from avoiding pregnancy for years to desperately hoping for it, and the modern pressures on women to time their lives – and bodies – perfectly.
[08:32] Anna, on shared pregnancy:
“Bro, unless you’re carrying half of the child, you’re not pregnant. Your wife’s pregnant. You had sex, had a really great time, and now you get to wash your hands of this for the next nine months.”
[19:12] Anna, on the odds:
“There’s only a 20% chance that you can get pregnant because it’s just that hard. So for the people who, like, accidentally get knocked up...you are a fertile nymph. Who are you?”
[21:36] Anna, on sex ed:
“When I first learned about the reproductive system, I was like 16, I was still a virgin...Nothing really sticks with anybody until it’s relevant to them.”
[28:34] Anna, on solidarity:
“For anybody listening, if you’ve had a really hard time getting pregnant, I now understand why it sucks so much.”
[36:08] Anna, on unsolicited advice:
“If you tell me to take Mucinex one more time, I’m going to scream. Like, I just can’t.”
Anna’s signature is raw, comedic candor—she curses, self-deprecates, and leaves no vulnerability unturned. Her tone oscillates from biting sarcasm (“Bro, unless you’re carrying half of the child, you’re not pregnant”) to generous solidarity with listeners who feel “too much, think too hard, and talk to themselves in the shower.”
If you’re trying to conceive, considering it, or have felt pummeled by fertility expectations, Anna’s message is this:
You’re not alone in the mess, the math, the madness, or the agonizing wait. Go easy on yourself. Eat the sushi. And ignore anyone who tells you to take Mucinex.