Anna Kai Has Brutally Honest Advice For Your Single Era

Anna Kai knows a thing or two about dating. “Most of my advice comes from experience, and really failing in every aspect throughout my twenties,” the tough-love TikTok star tells Bustle.

Kai, who began her online journey posting GRWM-meets-girl talk videos during the pandemic, has since garnered a following of over 3 million across platforms, and recently launched her podcast Brutally Anna, to take the conversation over 90 seconds. Kai’s handle — @maybeboth – is a testament to her Chinese American heritage and the feeling of living “in between” identities, which she credits as an identity in itself.

Kai started her content journey as a home decor blogger and fashion enthusiast. In 2022, a viral video of her applying her skin care routine and discussing the doom of dating “Chads” in New York took off, establishing her passion for a different conversation— relationships, including the one you have with yourself.

“Nothing was working out for me. My career, my relationships. And everyone around me was hitting these massive milestones in traditional careers, when I decided to pursue a creative path. By my late twenties, I still had nothing to show for it,” Kai shares, referring to her journey as an aspiring actor.

Her career as a creator took off while she was dating her now-husband, and she still shares vulnerable, funny dating stories from her past in New York. (Kai now lives in Connecticut.) Although she admits to having “a few hate follows,” she’s OK with that. “They drive up engagement, its fine.”

“Overall, my life did work out, because I chose it,” she says. “My message is that even if you don’t hit whatever milestone you envisioned for yourself at 30, it’s going to be OK. You can ‘make it’ later in life.”

What is your advice for women dating in their mid-to late thirties in regard to the assumption that marriage and kids is on every woman’s mind?

If a guy feels pressured to get married or have kids right away and is using that as an excuse to slow things down, he’s not your man. Also, if you’re a man in your mid-forties and that’s not what you’re looking for – why the f*ck are you dating a 36-year-old?

How do you feel about prenups?

I have a weird opinion on this that isn’t very mainstream — I only believe in prenups when there is an extreme discrepancy between the two people, especially if there is family or generational wealth involved. I didn’t get a prenup. That being said, if it doesn’t work out between my husband and I, I’m prepared for what could be a financially messy divorce.

I want to talk about Chads. How would you describe them?

A Chad is a man who is overly confident with no self-worth. I dated a lot of men who were perfect on paper and had thriving careers, but were absolutely prime candidates for therapy and never got it. That is also the problem with toxic masculinity. We have to normalize men talking about their feelings aside from when they have a microphone in front of them on a podcast. A “red pill bro”? I’ve had enough.

How do you define “dating someone” vs. “seeing someone” in today’s romantic vortex?

My general rule of thumb is three to five dates is “seeing somebody.” After five or six dates, you should know if you want this man to be your boyfriend and consider [it] “dating.” After three months, you should know if he’s your boyfriend, and if you’re not sure, the answer is probably no.

How do you address the dreaded “what are we” conversation?

You say it! You say, “I’ve loved getting to know you, but I am looking for a committed relationship. If you’re not on the same page, I totally understand, but I cannot continue seeing you any further.”

That’s so hard.

I know — because our desire to not be alone trumps our desire to be treated well.

How do you develop higher self-worth?

Confidence [comes from] practice. I never felt confident in my twenties, and even now have huge moments of self-doubt. What keeps me going is knowing that you don’t need confidence to do things — you can just do it and let it scare you anyway.

Are there any self-care rituals that you rely on to feel your best?

Say no more often — and don’t feel bad about it.