Should we go for it? This was all my fault. I suggested oysters for our first date because we had chatted about how much he loves the ocean, how much I love oysters and how his family trips to the Oregon coast had never included these slippery little shellfish.
But this delicately lit restaurant is not cheap. And, of course, he loves the oysters and wants to order more.
Based on my dating experiences in Portland in the American state of Oregon, there is a 50-50 chance we will split the bill. And if we do, my credit card might be declined.
Then, he will know I am a mess of an adult who can barely pay her bills lately - but wow, these oysters are good.
My first-date outfit says I know the difference between Kumamoto and Shigoku oysters and can afford to splurge on them both.
I am determined to maintain this veneer of class. "Sure." I answer. "Let's have another dozen."
As a freelance writer, I have accepted that I will never make a ton of money. My life is an endless loop of hustle, hope and fear.
My pay cheques arrive sporadically and, sometimes, they are just not enough. For those who have never navigated the "gig (freelance) economy", it can be difficult to understand.
The incessant fear of running out of money is exhausting. So is dating, these days.
Everything feels like a gamble. Will this person I just met online prove to be a waste of my limited spending budget?
For the most part, I am okay with not having lots of money. I buy my clothes at thrift stores and my drinks at dive bars.
Experiences are more important than things.
But as I head into the heart of my 30s, I sometimes wonder what potential partners will think of my tumultuous financial situation.
I also wonder if I can afford to find someone special. After all, dating is not cheap.
Even when I am treated on the first date, I believe that dinner and drinks should eventually be a shared expense. Most of the men I meet agree. But if someone I am dating has more expensive tastes than my own, that can prove tricky.
Luckily, my date picked up the bill that night after a half-hearted protest on my part.
As I walked back to my car following our first kiss, feeling the flutter of an enjoyable evening with someone new, it struck me that maybe dating with barely any money in my checking account was not a good idea.
I hoped he was interested in a second date, but could I even afford it?
Is it irresponsible to look for love when I have student loans and credit card debts waiting to be paid off?
When I met this new guy, I was not so sure. Would he meet the best version of me when money was constantly weighing on my mind?
Stress is not sexy. It makes me irritable and distracted. It can also make me overly critical and resentful of others. But conversation flowed effortlessly on our first date and I was able to stop thinking about work.
As we wandered into the usual first-date territory, I crawled out of my anxious hole and turned my attention to lighter topics: favourite movies, funny stories and those delectable oysters.
He made me laugh, which I had not done enough of lately. And he told me that he liked my smile.
If I had to give him my checking account balance, maybe he would hurry out and never call.
But in forgetting my finances in favour of a casual conversation, I showed him a more carefree side of me - one that people had not been seeing enough of lately.
As I drove away from our first date, I thought about how we would almost definitely see each other again. But then what? Could I afford the additional cost of drinks and dinners out each week? That is what dating is, is it not?
Turns out, a tight budget can do wonders for creativity.
We have since gone on bike rides around the city, hiked through a torrential downpour and woken up at 4am to see a sunrise over wildflower fields.
All of these experiences were cheap. They were also a lot of fun.
It did not take long for me to open up to the new guy about my precarious financial situation, which prompted him to open up about his own money stresses.
Despite those challenges being drastically different, our ability to talk about them made me realise we were on similar pages.
I am a firm believer that self-improvement should come before relationships.
I want to be the best version of myself when I meet someone new. But I have come to accept that we are all works in progress.
And if you find the right person, maybe you can keep working on being better together.