My boyfriend (36M) and I (29F) have been dating for 10 months. This past year has been one of the hardest of my life, I lost my best friend and cousin unexpectedly (we were also neighbors and very close), and shortly after, I experienced what I believe was an unfair clinical failure in my doctorate program. I was supposed to graduate next month, and now everything is on hold. I’m sharing this not for sympathy, but just to explain where my mental health is at right now. I’ve truly not felt like myself since these events, and things have only gotten harder as I’ve started medication and I do not feel like myself even more.

My boyfriend and I haven’t taken a trip together yet, and with classes restarting in June, we both agreed to try and go on a vacation in May. I’m a broke grad student, and he comes from a wealthy background, he has a trust fund and family money, so he’s very financially secure.

I mentioned that I’ve always wanted to go to Turks and Caicos. It’s been a dream of mine for a few years, and my friend who was supposed to go with me last winter backed out. I also feel like if it’s our first trip together, we should make it special and stay somewhere nice. I told him I’d pay for my flight and could even split the hotel cost if needed.

He told me he wants to cover the trip since he knows I don’t work much right now, but also said it feels unfair that I’m the one “dictating” where we go. He suggested we pick somewhere more budget-friendly and mentioned that other islands have the same kind of beaches.

I get wanting to compromise, but I find it frustrating because 1) I’ve had my heart set on this destination, 2) we haven’t spent any money together on travel or big plans, and 3) he’s extremely wealthy, so it’s not like I’m asking for something far beyond his means. I’m not expecting luxury every time, but this one trip feels really meaningful to me.

I just don’t know if I’m being unreasonable or if this is a red flag in terms of how he views shared experiences, money, or empathy. What do you guys think?