When he asked me to spend the weekend with him in Denver, I said yes before I gave it a thought. About half an hour later, we were still at dinner, and all the thoughts started to bombard me: this was our—what?—fifth date, maybe? Go away together? It sounded like a recipe for disaster, particularly where money was concerned. I started to panic.
There was no backing down, and I didn’t want to, anyway, despite my reservations. He told me we’d stay in a hotel, somewhere nice, and spend the night downtown. “Okay,” I acquiesced, “you pick the hotel, and I’ll split it with you.”
I could feel that I wanted to express an openness on the financial front right from the start, so we’d be consistently on the same page.
On the drive down, I suggested an old vacation trick that my mom has been singing the benefits of for years. She calls it the kitty, when you each pool an equal amount of cash into a collective envelope, and spend from it until its gone, at which point you each contribute another, equal amount.
He was receptive to the idea, so we gave it a try: we each put in $100 cash, and it was decided that he’d be the keeper. First thing: we arrived at the hotel, and we had to tip the valet. No scrambling for a few dollars or deciding whose money we used, no squaring up afterwards, just an easy exchange from our collective money pool and the guy out front. We seemed to be in business.
All weekend, we found the collection not only useful but a perfect way to take the pressure off the question of money, splitting bills, and who owed what. As he put it, “It’s like we settled up before we even went out,” and at drinks, dinner, more drinks, cover charges, and all kinds of instances, we didn’t have to duke it out over who was more generous, over who was faster with the credit card draw, over who might be more into this budding romance than the other.
We agreed that it was an excellent idea. Moms do know best.
Because of our relative compatibility when it came to an egalitarian dating philosophy, we found the system to work well, but I could see a few drawbacks. Certainly, if one party was inclined to spend more, drink significantly more, choose a restaurant or bar outside of your range of spending comfort, the more conservative party might find themselves feeling a little overwhelmed by how quickly cash disappears. There might also come a time when you feel genuinely moved to treat the other person, and you could throw off the beautiful balance of the collective fund, even with good intentions.
We found, however, that it worked for the short duration of this particular weekend, and I especially enjoyed being free of the responsibility of paying at all. Plus, because you’re working with cash, you’re always aware of your bank balance and know if you’ve gone overboard. Every once in a while, I’d ask how much money we had left, and if I needed to contribute, but because we both knew we’d put in equally, there wasn’t any qualm. Even he admitted to feeling the relief of some imagined tension around spending money with this little system.
I’d give this trick a try on a weekend away with a friend or even in a small group—though if there are couples, I can see how things could get a little messy. Still, it’s worth a try—it’s mom-recommended, and we approved.
He did one funny financial move that made me wonder, though, which was that he always asked me how much I would tip – a little quirk I found both amusing and concerning. Either he didn’t know how great a tip was appropriate (“I always tip 20%,” I repeated, more than once), or he didn’t know how to calculate 20% from the bill as fast as I do.
Both of these leave me a little concerned for his financial health, and wondering about future dates.
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