Let’s just get this out of the way: Dating in the age of technology is pretty horrible.
We spend our days furiously swiping in various directions in search of Mr. or Mrs. Right (or Right Now), starved to find a match with a little more this or a little less that. And when the Tinder Gods smile upon us and grant us one strong possibility out of the dating pool, we find ourselves in a swanky hotel cocktail bar thinking, How much are these overpriced margaritas gonna run me? Do I have to follow the ridiculous routine of putting my card down, him pushing it away, me offering again...?
Like it or not, money is intimately intertwined with dating. What’s more, the allure of meeting someone via an app also carries uncertainty of how that person chooses to spend, save, and manage their finances.
The anecdotes below are real-life examples of how money can interfere with the dynamics of a first date, as well as a few cases where flexibility and frank discussion on the topic transformed one online conversation into something more.
Do we really need an Uber XL?
“I was on a date with a guy who took me to a fancy restaurant – average dialogue, overall 'meh' experience – and he suggested we head to another bar. I thought I would give him one last shot, so we went outside to catch a cab… or so I thought. He insisted on ordering an Uber XL that took forever to arrive. Even when I suggested we save time (and money) with a taxi, he said 'the night would be ruined without the XL.' As if the universe was teasing me, I saw one open cab pass by, then two, then three… soon I counted 15+ available cabs. I get that he wanted to impress me with a spacious Escalade, but you know what’s more impressive than an Uber XL? Being smooth and going with the flow.”
Even a “free lunch” can cost you
“I met my first post-college boyfriend on Tinder and he was the epitome of the finance bro: smart and good-looking investment banker, strong personality, and hard worker. I knew he cared about saving money because he lived with his parents and stayed at work past 8 PM to eat dinner for free, but soon I learned the difference between being frugal and cheap. When he took me out for meals, I noticed that he purposely chose places where he could pay with gift cards. When I won 10 free rides with Lyft through a work competition, he purposely slept over to use them to go to work in the mornings. I’m all about saving money too, but when you are excessively cheap with the people you care about most, it can make them feel like they don’t matter to you.”
Let’s meet at my hotel - the one I own
"I hit it off with a girl who came from extreme wealth - Saudi royalty wealth - but had no idea what kind of date to take her on. I actually brought her ice skating (which went surprisingly well), and later her friends texted her asking us to join them. We met them at one of the city’s best hotels - which she owned, literally - where they bragged about their latest investment ventures. The hotel rendezvous was followed by a $400/ person dinner and $3,000 bottle service at a club. Even though one of her friends picked up the entire tab, I was uncomfortable with the whole experience. I was so out of my league. We ended up dating for a bit, and sure it was nice to be pampered, but I couldn’t stay with someone who didn’t see eye-to-eye with me on the value of a dollar."
Love can conquer all (including unemployment)
“When my girlfriend and I first met through the apps, she was still looking for a job while I was employed. Naturally I was happy to pay for 99% of our meals and activities, but as days became weeks and weeks turned into months, I secretly grew resentful of the disproportionate costs in our relationship. There was little progress in her job hunt, and after six months I mustered enough courage to delicately share my feelings. I couldn’t have made a better decision – she had no idea how I felt and was so glad I told her the truth. Even without a job, she made the effort to find free activities for us, buy small snacks, and was more appreciative than ever when I paid. As scary as it was to talk about money, it was beyond worth it to learn just how caring my girlfriend truly was.”