My boyfriend and I are planning a trip to the islands. I suspect I make more money than he does. This is our first big trip together and I'm kind of nervous about who is expected to pay for what. Should I offer to pay for some stuff or split shit?
Dear Paid For,
Thank you for bringing this issue up so that I can once and for all clarify the rules so everybody understands what the hell is supposed to be going on. In its most elementary form, the paying issue comes up in the form of a bill situation at the end of the date. There are several acknowledged tactics that are in wide usage regarding the date bill, namely a) the strategic bathroom departure, wherein you conveniently go to the bathroom as the second round of drinks is winding up and when you return to the table the bill has magically and "surprisingly" been paid, b) the vintage fake-reach bag fumble wherein you "offer" to split it and fake rummage through your bag pretending to be looking for your wallet which ends with the date's insistence that it's his pleasure, and c) pretending not to see the bill while maintaining conversation and eye contact as the date pays the bill.
Having been on many MANY dates with guys ranging from alarmingly poor to disgustingly R$CH, I have determined that the ONLY acceptable tactic to implement is approach c), i.e. paying for nothing and letting the date pay for everything. This is because if you are seriously considering relationshipization and regular sexifying, if they're not paying for cheap shit like drinks upfront, you're basically signing yourself up for a future of construction paper cards, macaroni necklaces and Dulce & Fontana bags. Similarly, if your boyfriend can't foot the bill for your island vacation IN ITS ENTIRETY, you can pretty much take your dreams of quitting your job and watching Bravo all day long and throw them out the window because if you get married you'll have to CONTINUE working until you die which is in no way acceptable and 100% defeats the purpose of getting married which is to get someone else to pay for things and to have someone to complain to. I hope this answers your question.