I actually have had this question asked a few times in regards to wanting solid advice on what is the right thing to do in terms of how couples should handle expenses while on vacation when they are ‘just dating’ (not married and perhaps have only have been dating for a short time). To be honest, there really is no set answer to this one because there are so many factors involved and each dating situation is different. For example, are we talking about a weekend getaway or full week vacation overseas?
I think that if one person (usually the man but hey, it’s 2020–anything is possible nowadays) is paying for all or a contribution towards your travel expenses such as the flight and accommodations then it can be expected that once you arrive at the destination, you can pick up a good amount or at least some of the food and entertainment tabs. Personally, it just feels good to reciprocate if someone is that generous to pay most of or all my travel fees up front.
If both people are paying separately and in this case for me as the woman, the man I am dating is not paying anything towards my personal travel expenses, then I do not really expect to pay for meals or much during that time away. In a normal situation when I’m NOT traveling, I do expect a man to pay for most meals (unless it is a special occasion or I am asked to pay the tip). Why? I firmly believe in gender roles and that they should still exist. Whereas I know not everyone might feel the same because the counter argument could be that most women are in the work force today. If a woman has a stable career/job and can pay for meals as well, why is she not paying those bills? I totally understand this way of thinking, it makes sense to me as well but it does not change the principle or belief that I have which is that a man should want to pay for the dates. It actually for me has nothing to do with money being spent but to do with showing a woman that he wants to take care of her along with being chivalrous and conveying his financial strength. Especially in the early stages of the dating game, if a guy is asking the woman to go 50/50 or to pay for dates, then my immediate thought is, “Next.” I do not mean that in an entitled, conceited, or stuck up kind of way. I might still stay to get to know the guy better but I am not going to invest too much of my time because I have been in the dating game long enough to know that this is the golden standard (if you ask most men, they actually do want to pay) and there are an abundance of men who would never ask a woman to take her wallet out. So why would I make an exception now or settle for someone who is a 50/50 kind of guy? I actually do not encounter those kind of men in my life because I set my standard from the start what my expectations are (which mind you, I don’t think is even much to ask) and if this were to be a problem, my response would be, “Then don’t date me.” In other words, I am not going to lower my dating standards as I could keep it moving at that point. However, with travel, I recognize things can add up fast depending on where you go and how long you are away in which I think offering to pay for things from time to time is classy and often appreciated.
Note for Men: I think it is extremely important to consider, if you do NOT plan to pay for much during the trip or expect a more equal contribution financially with how money will be spent throughout the duration of the vacation, then you absolutely need to have this conversation and set those standards. Just as it is important for women to set standards, men should be doing this as well. I have had many male friends complain to me how they do not like having to pay for things all the time when they are dating–especially if there is not a relationship status or if they are unsure how much they like the other person. I ask if they have expressed that to the person they are dating and often times the answer is, “No.” Most women would not know this is bothersome unless it is brought to their attention. Chances are, they would be more than willing to contribute or to pay for things too. Like anything in life, you just have to ask.