“Let’s address the elephant in the room,” he said during our conversation over the phone (yes, actually talking) the evening before our first date. This handsome, 40-year-old man I met on Tinder wanted to talk about the fact that I am white and he is black. However, race didn’t turn out to be the difference that was insurmountable to our sensibilities, it was money.

This, my friends, is the latest in my dating saga which frankly is getting a little emotionally exhausting. I’ll go into that bit later.

Vito (alias) is tall, accomplished, owns his own home, adopted a dog and seems to enjoy what he does. Good start. What I didn’t realize until I was out with him is how badly he wants status as well. I’m not sure where he thought I fit into achieving that goal, but I’m not interested.

It began innocently enough – when he asked about the colleges my parents and siblings attended, inquired whether one had to be millionaires to hang out with my parents (um, no.) and casually dropped that the cost of living on the West Coast (the subject at hand) was far too high for him to accept a $200,000 job offer. At this, I almost choked on my gherkin!

That question came a few minutes into the first date. See, Vito is a wine lover. So we were at a wine bar. Hence the charcuterie board. Hence the gherkin. You need a sour jolt to the palette every once in a while, but I didn’t realize that the night itself was pickling as I took my first tangy bite.

He went on to ask if I was at the top of my track where I work, insinuated he thought I made well over $100k and asked what kind of furniture I had in my home – which I realized later was simply to bait a return of the same question.

In case you were wondering, his interior aesthetic of choice is mid-century modern, purchased entirely at Mitchell Gold. He then showed me photos of each of his immaculately decorated rooms, which frankly looked more like a magazine than a place I’d really want to hang out. There was no personality, no plants, no place to abandon my Vanity Fair and empty wine glass. But I digress. I think the entire line of questioning about interior design was ultimately to show me his top of the line kitchen after which he suggested I could choose the menu for the dinner party he wants us to host. And I could cook it … if I wanted.

Seacrest out.

This man was looking for a pawn, not love. A woman who fit his ideal, of high status and high standards. Problem is, you can’t find love by looking at someone’s resume or even their Restoration Hardware receipt. As if. “I dreamed a dream in days gone by….”

What upset me about this one was less about the invasive questions around status, which I do not have. It wasn’t really about the talk over money either – though at one point I think he might have been trying to find where I drew the line. It was the fact that during the conversation before our first meeting, I divulged a lot about myself at his request: my past relationships, my family dynamics and my hopes for my future. As I was pulling away from the club filled with 23-year-olds where Vito and I had no business being, I felt like a fool; fileted for all to see.

He deliberately and prematurely peeled back my layers to see if I was up to snuff. And as I tend to be easily disarmed, I let him. In doing so, I feel like I gave myself away – and to a guy who was more interested in my paycheck than my heart. It hurt and I did it to myself.

The realization that my disappointment lies with myself, not with Vito, reminded me of a conversation I had with a friend of a friend, Nancy, earlier this year. She cautioned after my heartache over Mr. Rugby that I keep in mind not to give too much of myself away. At the time I thought, ‘Well, isn’t that kind of part of the deal of dating? Aren’t you aiming to be open and vulnerable with someone so they truly get to know the real you?’ I think the answer to that question is still yes. However, I think I’ll proceed by playing it a little closer to the vest and waiting to get to know the person I’m revealing myself to organically. I don’t think I could handle waking up with another hangover of personal regret anytime soon.