I remember one dinner vividly, it really stuck with me. I was up in Lake Tahoe for the weekend, and this nice guy around my age asked me out to dinner. He was kind of quiet and shy, sort of hovering around the edges of my friend group. He wasn’t exactly the most handsome guy, and to be honest, I wasn’t really into him. But he seemed nice, so I figured, why not? I didn’t know how to turn him down. I was still struggling with my weight – not feeling very confident, especially compared to the gorgeous women I was hanging around with.

For years, my dad had hammered into me how overweight I was, so I ended up measuring my worth by my size rather than my intelligence, athletic skills, or beauty. So, you can imagine, being asked out felt like a big deal. I went all out, got dressed up, and he took me to one of the fancier restaurants in Tahoe.

But then, early on in the meal, my date dropped a bombshell. In this serious, awkward tone, he turned and said to me, “I just want you to know, if you’re not into me, we can just leave. I don’t want to be spending money or my time with someone who doesn’t really like me.”

I was completely thrown. Intimidated, uncomfortable, you name it. What was I supposed to do? Walk out and be like, “Sorry, but I’m not really feeling it”? Admit that I wasn’t that interested, but I was just so psyched to be asked out that I said yes? Or go with what I did: “No, I want to be here,” even though it wasn’t entirely true? I was scared that if I told him the truth, he’d just bail, and I’d end up feeling like crap for hurting his feelings. We never went out again, and I felt awful about it. Money became this awkward issue that I didn’t know how to deal with, even though it wasn’t really my problem.

I know plenty of women – back then and even now – who wouldn’t think twice about a free meal or having someone take care of them financially. So why did I feel so different? Why did it feel like I wasn’t allowed to be taken care of?