Proof of Life with Preston Rakovsky
Jul 27, 2026 · 42 min · 11 segments
A woman who spent years testing her boyfriend's love through hypothetical worst-case scenarios explains how a random question about turning into a worm on the New Jersey Thruway cracked open a pattern…
Zayana PowellGuest
Preston RakovskyHost
[laughs] I would s- I'll tell them like, "Hey, I need you to do X, Y, and Z for me." Or, "Hey, I'm feeling not heard." And instead of someone being like, "Yeah, I hear you," they were like, "Well, you're asking for too much."

I feel like this anxiety, which like as a kid is like kind of funny and cute, I, when you get older starts manifesting in your relationships.

I usually always give to my partners ins- and they never give anything back to me.

So what I mean by that is this: My very, like first romantic experience ever, you know, I was friends with the guy, but I didn't really feel anything, right? He didn't really give me anything.

You gotta take what you can," right? And so I kinda got accustomed to this idea that I'm never gonna get that direct communication that I need, and I feel like, you know what? I'm just gonna go through it people-pleasing.

When we talk about like the people-pleasing and the jokes, how did that start affecting your relationships?

And the way that I would try to express my needs is through, again, these weird hypotheticals.

So like for example, I could be like, we're in Central Park, right? I had a partner that didn't really like going outside much.

I'd be like, "Would you be like upset if one day we just randomly just like went to Central Park and just sat down? You know, just, just, just putting it out there."

[laughs] I would s- I'll tell them like, "Hey, I need you to do X, Y, and Z for me." Or, "Hey, I'm feeling not heard." And instead of someone being like, "Yeah, I hear you," they were like, "Well, you're asking for too much."

I feel like this anxiety, which like as a kid is like kind of funny and cute, I, when you get older starts manifesting in your relationships.

I usually always give to my partners ins- and they never give anything back to me.

So what I mean by that is this: My very, like first romantic experience ever, you know, I was friends with the guy, but I didn't really feel anything, right? He didn't really give me anything.

You gotta take what you can," right? And so I kinda got accustomed to this idea that I'm never gonna get that direct communication that I need, and I feel like, you know what? I'm just gonna go through it people-pleasing.

When we talk about like the people-pleasing and the jokes, how did that start affecting your relationships?

And the way that I would try to express my needs is through, again, these weird hypotheticals.

So like for example, I could be like, we're in Central Park, right? I had a partner that didn't really like going outside much.

I'd be like, "Would you be like upset if one day we just randomly just like went to Central Park and just sat down? You know, just, just, just putting it out there."
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