Hey! I recently started dating someone, and it is both of our first relationships. We have only been dating for 5 months. We both go to the same college in NY, and we recently decided to make a 3-day road trip in Early September.
The financial discussions for our upcoming trip have been a bit awkward, and we sorta decided that I will be footing the bill for the hotel, while he would cover gas and food. I felt like this was a bit unfair, as the cost of the hotel is probably ~3x what gas/food would cost us. I had brought this up and I noticed it was a bit of a trigger for him, and it was clear he wasn't too keen on having the discussion. I don't think this comes from malice, but more so that money discussions are always awkward, and this is both of our first relationships.
I had offered to split it so that he pays a quarter of the hotel charge, and he sort of reluctantly said yes, but mentioned he doesn't have the money right now, so I didn't really push further.
Both of us have different perspectives on money - he is a lot more frivolous than me in spending, while I'm pretty frugal. Even though we're both in university, I have more disposable income than him (mostly because of my frugality).
I'm worried that I will resent him during and after the trip because of this, and I know I need to bring it up to him, but I don't know how I should approach it. I do really want to go on the trip, and I realize that I may be too "cheap" and should let things go. At the same time, I'm feeling more and more resentful whenever he mentions how he spent money buying (non-essential) new clothes or books. I've been bottling it up for a bit since he's going through a bit of a rough patch, but the date of the trip is approaching and I can't keep my mind off things.
To clarify, my questions are:
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How do I bring it up to him? I'm worried if it feels like too much like an ultimatum, we'd have to cancel the trip.
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Should I just "suck it up"? I know in relationships things aren't always equal. I would like to think if the roles were reversed he would do the same, but I'm not sure if he would.
I can not emphasize how much I like him. My post may have made this sound like a toxic relationship but it is anything but. It's just one small part of an otherwise amazing relationship.
This seems like a rather practical problem and you have gotten so much good advice so I'm going to address it from a different perspective.
I do have a bit of the impression that you are more inclined to this penny counting mindset, probably because of your frugal nature. It is important to consider your own shortcomings and decide if they are a significant contributing factor to a problem. (Within reason, people being abused are often disproportionately convinced it is their fault/responsibility)
I think you got good advice for how to talk to him. I think the next part is to also figure out what you can do to not have this constant tally of who spent what. And then discuss it with him because it's not totally implausible that he has picked up on it. Maybe you spend more but consider if he contributes more significantly to the relationship in other ways that you may fall a little short on. And maybe don't judge too harshly on books and clothes if they are still occasional and cheaper, we all probably spend at least $100 a month, call it sanity tax, where we buy things that make us feel good and keeps the dregs of daily life, obligations, and stress at bay.
Perhaps do use the app everyone suggests for bigger things like planned trips or outings that are obviously going to be over a certain amount you both agree on.
Please keep in mind a lot of this is based on assuming the best of both parties. You're not wrong for feeling uncomfortable and worry about being taken advantage of. I just wanted you to pause and reflect on that a little more and if it is worth addressing as well, and if so how.
I think this is a healthy conflict to have and how you both navigate it is going to lay a lot of groundwork for the relationship!
(Edit: this was originally started as a reply to a comment and then I was like fuck it I'll make my own but now I realize it looks way more negative to you out of context! It started as a response to where you said you find yourself penny counting)