“If your ship doesn’t come in, swim out to meet it!” -Jonathan Winters
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I know, it seems like a strange topic for the second post in our financial journey, but I wanted to share a bit about how we met. I believe the relationship with our partner and the conversations we have are some of the biggest factors in shaping our financial journey and success.
Initially, I planned to talk about how we met, our passions, work, marriage, and the state of our financial disaster up until about four years ago. However, as I started writing, I realized I couldn’t leave out the details of how I managed to massively irritate Anna for weeks—so much so that we ended up having a fight before we’d even said more than hi to each other and certainly before we went on a first date.

How we met
Anna and I have an inside joke whenever people ask how we met: we met at a place called Circuit City.
If you’ve heard of Circuit City, you’re probably at least in your mid-30s to late 30s. We get a kick out of it when people just give us blank stares and ask, “What’s that?” Back in the ’90s, Circuit City was huge, but by 2009, it had officially gone out of business. We usually explain that it was an electronics store, kind of like Best Buy.

But it wasn’t love at first sight—mainly because I was an oblivious guy who had zero interest in getting to know Anna. I completely ignored her, and Anna was not happy about it.
To take a step back, I started working at Circuit City in 2000 during high school, then through college, and into my first office job. In the summer of 2005, while home on break from college, I called up work and asked, Would you mind putting me back on the schedule for the summer? My boss replied, Yes! I woke up, grabbed my finest Circuit City work shirt, which was a couple years old by that point, drove to work, and walked behind the customer service counter. I swiped my badge that I kept on my hip, clocked in, and greeted my first customer.
There was this girl behind the counter who I’d never seen before and I was fine with that. I was just there for the summer and probably wouldn’t see her again in a few months. I certainly wasn’t looking for love. I’d kind of given up at that point.
Week, after week, after week passed and I said the few words to Anna of hi, how are you, how’s it going? Just surface level conversation.
One day, Anna brought in one of her best friends to inspect me, covertly of course. She came up to me with a CD (that thing that stores music before everything went digital). I rang her up, and that was really about it. Some time passed and she brought her parents in to buy a new digital camera for school. She was going to George Mason at the time and getting a degree in art with a concentration in photography. I was pleasant with her family, but I certainly didn’t go out of my way. I have no idea what they thought of me after that first encounter.
One night in June I walked in to find only Anna behind the front counter. Just the two of us and the awkward silence that can be deafening. The night was also slow… (few customers in the store). I said Hi and proceeded to clock in. After an hour of barely a hello, Anna turned to me and said, Either this can be a really long night for you or a really short night. It just depends on whether you want to talk to me or not. I just stood there, most likely with a dumb look on my face and said, How are you doing?
After a few weeks of actually talking, Anna wanted to get to know me better outside of work. We usually worked the 6 PM to 10 PM shift, and one night, she started dropping hints about being hungry.
I can just picture the steam coming out of Anna’s ears as the evening dragged on. This pattern repeated for hours, with both of us getting increasingly frustrated. Anna was mad that I didn’t ask her out for dinner, and I was mad that she kept telling me she was hungry—because, in my mind, her shift would end soon, and she could just go home and eat. WTF… Seriously…
Finally, she got so frustrated that she turned to me and asked, Do you want to get dinner after work? To which I said, Sure. Not exactly romantic, I know. In my defense, I was sick to the point where my voice had almost disappeared. But honestly, even if I’d been 100% healthy, I probably still wouldn’t have picked up on the hints. Again, I’d kind of given up on love at that point.
Anna had potato skins, and I had tea with honey. Romantic…
And that, surprisingly, was the start of our relationship. Maybe even a first date? Anna then invited me to a pool date at her college to “check out the hardware.” The software portion was tolerable, but clearly buggy and needing more work. Then she invited me to another dinner date with a girlfriend to get her opinion. Receiving approvals all around—despite my earlier behavior—we became a couple.
For the record, I did call Anna my girlfriend first, I did say I love you first, I did ask her parents if I could marry her, and I did propose to her. So, I’ve got a few points to my name. But let’s be honest—Anna taking the initiative has always been the main theme of our relationship. That trend continues through our financial journey, even when I (kind of) threatened divorce because of our finances. But that’s a story for another blog.
In the next post, I’ll talk about the time Anna asked me an innocent question, What are your thoughts about combining finances?
I wrecked our relationship for months with my response…