Vacation Is Calling
By this time tomorrow night, this is where I’ll be:
The beautiful Waikiki Beach in O’ahu, Hawaii!
Go ahead, you can hate on me. LOL!
But listen…my weekend has been so busy, I haven’t had time to schedule any future posts for you guys. I sawwy.
Hopefully, I’ll have lots of shenanigans to share when I return.
Oh wait, I have a good question for you…
If you were in a relationship that wasn’t defined and decided to go on vacation together - how often would YOU offer to share the expenses, if at all?
Aloha!
~*~*~*~*~*~Work to achieve, not to acquire.
And always, BE FABULOUS!

This blog is the story of my life...a single mom who worked her way from nothing to financial freedom. Subscribe here and follow the rest of my journey.
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Well, if you’re vacationing with a “friend” then you wouldn’t expect a “friend” to pick up your expenses for you. So, you’d keep a record of the big expenses (food, excursions, tickets, transport) and then divide it. A few bucks here or there you might forget about.
But if you were really into your “friend” then you might pick up some things and not show your “friend” the bill.
The question isn’t about ME, it’s about YOU. What would YOU do? [-SM]
If I was invited , depending on the level of the relationship(read-if we are shagging) , I would let the man pick up the hotel and traveling expenses, however I would offer to pay for this or that from time to time-like take him on a helicapter ride for two and foot the bill on my own. Or pay for lunch here and there and dinner here and there. After all, I want a guy to have a good time too and not to have to think about expenses or the fact that his GF is a totally inconsiderate bimbo. If I make less than him-I will let him treat me and offer to pay here and there. If I make more than the guy-well, I am staying home in that case-to struggle pay the bills I can in New York thank you very much, no need to go to an exotic vacations.
First, have a wonderful time. Now to the question: I would pretty much insist on paying something, especially if the relationship is undefined. I would probably pay for at least the dinners/meals for the trip.
If I’m going on a vacation with just the two of us then the gentlemen should bear the brunt of the expenses. I’m willing to get pick tickets for this or that or a meal here and there, but the trip is his treat. Now if he thinks that’s a burden, he can leave me home. And I type this as I sit at home, not going anywhere with anyone of the male persuasion! But really I think it kinda depends how it was decided to go on a trip. If I it was my idea or a mutual decision, I’ll probably pay for my flight and be willing to split the room. But everything else is on the gentleman.
Have a great time in Hawaii.
I would offer to pay for the meals or you could pay for the rental car and split the cost of meals.
I would pay for some meals, when I felt like it, and maybe some activities… when I felt like it.
He invited you!
Just wanted to say… Hope you have a good time while you’re here. What are you guys planning. You should definitely eat at Macky’s Shrimp Shack in Hale’iwa (near 7-11) and shaved ice down the road at Matsumoto’s. Killer! If you need food suggestions, I’d be happy to help.
Have a wonderful and safe vacation.
Now to your question, it depends on a few factors. If the trip was the guy’s idea then the bulk of the expenses are his. However, I would on occasions volunteer to pay for a meals or other small events while on vacation.
It depends a lot. I’ll usually go on for a 50/50 share under this situation.
But it will depend a lot on relationship equation, in particular if you are looking for something more out of this relationship, they you may agree to bear the lion share.
Anyway, as a rule of thumb, you can divide the travel expenses in between you, and someone should pay for the meals while the other guy should pay for the dinners. It looks more generous I think.
Have a nice time.
have fun :D!!
hmm….i think i’d treat as if i were on vacay with the girls - 50/50. but rather than going half on every single thing, it would be like paying for one thing, while he pays for another.
We split everything 50/50, but if the relationship were undefined….
If he invited me, I’d let him pay for hotel/tickets, and maybe make a half hearted offer to cover mine. Maybe. I’d try to pay for at least half of the meals/entertainment, perhaps more, but if he insisted on paying, I’d have no problems with that either.
more importantly, how do you get a guy to take you to Hawaii??? I want to go!
Have mucho fun!! it’s gonna be rad, esp. if you have never been! Don’t forget to drive around to the other side of the island–it’s BEEYOUUTEEFULL.
If i were in your situation, where the guy just came up with the idea to surprise me, I’d honestly expect him to be treating most of the time–ie, hotel and flight expenses, and a few romantic dinners. However, I’d offer to pay for or split other meals and activities (snorkeling, surf lessons, sightseeing fees, etc.). It’s up to him if he wants to take me up on the offers…
If he and I both decided to go on vacation together, definitely 50/50–unless he made so much more than me that it would hinder him to ’slum’ at my cheapie choices in hotels and flights and dinners.
Have a great time, my wife and I had our honeymoon in Hawaii (we stayed for four days at the Waikiki Marriot), if you have a chance, check our Roys. They’re a Hawaiian fusion chain that we enjoy tremendously, it’s very frugally priced (their fixed price menu anyway) especially for Hawaii.
As for your question, I’m a little old fashioned and think that if the guy wants the relationship to go from undefined to defined, he would pay all the larger expenses like the hotel and any fancy meals. If the woman wanted to go 50-50, I’d respect that. If the woman asked me on a vacation, I’d pay 50-50. I know it’s a double standard but I’ve never had any complaints (and now I’m married so I’ll never get any!).
Undefined is just that, undefined. However, I agree that it would be a good idea to pick up some of the meals and smaller expenses (especially if you’d like undefined to move to defined!) After going out with someone a few times, I can always tell if he’s someone I’d want to be in a relationship with. How a man treats a woman says it all, and he’s probably looking at it in reverse. So yes, he should pick up the airfare and hotel since he did the inviting, but be considerate and help out with something! A little consideration goes a long way…
If he invited me, I would expect him to pay for the major expenses (airfare, hotel). However, I would cover some meals and activities. I would NOT go 50-50 or calculate anything because that seems too much like roommates or somesuch rather than a romantic (although undefined) relationship.
Single Ma,
I’m so there with you on the “undefined” relationship…I’m there too!
First and foremost, have a wonderful time. It’s not everyday that you get to vacate with a man when you’re in an undefined relationship. I’m sure you’ll see several groups of ladies there together and manless, which I’ve done with my girls on more than a few occasions, and I’m sure you can probably concur. Hawaii is a very romantic place so just bask in the fact that you are there with someone that thought enough of you to want to take you some place nice.
However, the type personality most of us independent women seem to be these days, I totally would have the same question regarding sharing expenses. Afterall he did invite you, but a lot of us have the “I don’t want no man saying he did xyz for me”…blah, blah, blah. I agree with the previous posts; I’d definitely offer to pay for some meals or tours but the high dollar items I’d let him pick up - i.e. room, flights - especially if the vacation was his idea.
ENJOY…hold hands…be a couple…this trip may just DEFINE your relationship.
Blessings, LiGhT & LoVe
Sage
Huh? Not sure I would go on vacation with someone where the relationship wasn’t defined. And since it’s not defined I would I would not offer to share anything.
It may be undefined currently, but not for too much longer I suspect. Gentleman don’t normally take women to Hawaii if they aren’t at least a tad bit serious. That said — pick up the tab for dinner a couple of times. And have too much fun and make sure you go to a luau and Haunauma Bay. Oahu is loverly.
Single Ma,
one more thing…if you have a chance also try to go to one of the other islands. Though I loved Oahu my first time to HI, I loved-eddid Maui and the Big Island. So much to see, so little time.
Sending positive LiGhT to your vacation…
Sage
http://www.sagewizdom.blogspot.com
I know you’ll have an awesome time! I’m planning to go to the ProBowl next February so I’m looking forward to your recap.
From what I’ve read about your guy, I suspect that after you offer he will set the tone for the rest of the trip. I would offer to pay for the first meal and say something like ‘thank you so much for taking me on this trip, you must let me buy the meals’ or ‘would you be offended if I pay for our meals?’ Most men I’ve dated would say something like ‘this is my treat, please let me do this’ or ’sure you can pay for 3 dinners’ - but usually when men decide to treat a woman like you (and me) that has her own, they want to handle things.
He’s taking you on vacation - so definitely offer, but be prepared to be treated the entire trip. EyeCandy seems like the type of man that won’t want you to come out of pocket.
There is a big difference in a male friend and a female friend. First off, have a blast on your vacation! Now, if it were me and my best, we have a big habit of paying for one another without thought! I will admit that most of my just male friends always pay when we hang out. I offer to pay, secretly wishing they decline! lol Which they always do. So I’d offer, here and there. Again have fun!
Ok, it’s official, I hate you LOL!
if I were invited to the trip as you wre, then no, I wouldn’t offer. Maybe certain things as a token of appreciation but I wouldn’t feel obligated.
GWAN and have fun!!!
It’s a hard hypo b/c I can’t see myself going on vacation when the relationship isn’t defined. But I’ll see it just like any other date - if I was asked to go, I’ll bring enough money to take care of myself… with no expectation of having to use it. However, I like to be generous so I’d probably offer to cover meals or activities sometimes. If it was my idea, I’m going to expect to shoulder more of the costs, though.
HAVE A GREAT TIME! And bring us back a souvenir picture of a Hawaiian sunset!
I think this vacation is an attempt at “definition” on Mr. Eye Candy’s part!
Anyhoo, I agree with Sistah Ant above, whose wisdom saved me from having to over-work my fingers this morning.
HAVE A WONDERFUL TIME!
And, hmm… I suppose if the relationship hasn’t been “defined” I’d pay for my stuff mostly — except meals. If he’s taking me out, he’s paying.
Regarding expenses, I’d follow his lead. If I wanted to do something specific, I’d pay for that unless he insisted. If he ended up paying for almost everything, I’d take him out for a super swank dinner on the last day.
Have a great time!!
I think it’s always best to offer to pay your share, but he probably won’t let you. Don’t worry to much about it though - those things tend to work themselves out pretty easily!
Have a wonderful time!
Single Ma - no advice, but have a wonderful Hawaiian vacation. My husband, daughter and I were there in December, 2007, and had a wonderful time. Can’t wait to hear about your escapades!!!
I would have figured out a way to discuss it before now. But then I’m really weird about it. Basically, after the first date, I explain my favorite philosophy of paying and I ask for his. Then we work out our compromise. Any time something out of the ordinary comes up, I ask how this should fit with our current compromise.
I would not do well not knowing how the paying of things was going to be happening.
Have a great time!!! I went to Wakiki for Memorial Day 2002. It was hands down one of the best vacations I have ever had.
If I made a decision to go on vacation with a guy, chances are ’something’ is defined. I would offer to pay for a dinner [or 1..lol] and I wouldn’t be offended if he let me. As a matter of fact I would probably insist. Afterall, I’m sure he will be spending also.
Looking forward to posts about your Hawaiian vacation! I always enjoy your blog. Hope you’ll make it to the Windward Side (Kailua, Lanikai) and North Shore (Waimea Beach is awesome) during your stay. Waikiki’s cool but the island has so much more to offer. I live near the HNL Airport and just love living in Hawaii!
Aloha!
Meganda
http://meganda-meganda.blogspot.com/
I would pick up the tab for events (e.g. windsurfing, jet skiing, etc) that I suggest and some of the meals. If he is a gentleman, things will work themselves out:-)
Bump that, being the sister that I am- I would have to ask him to define the relationship.
I would explain to him that I don’t do this with male friends, I came here because you invited me, however, now that I’m here, I feel a little uncomfortable.
In the meantime, have fun as if he was your girlfriend, It seem that he already paid for the big stuff. So you can chip in a little.
I would have to press for an answer, on the last day of the vacation. Until then, have fun