Would you pay for a girl’s vacation with you?

This topic seemed to be divisive in another discussion so I thought it deserved it's own thread.

Let's assume your GF or hook up buddy is either working at low paying job (admin assistant, non-profit, politics) or is still in college and doesn't have rich parents. She could only afford a modest trip for herself, but you want stay at a nice hotel or resort on the beach.

You make investment banking / PE money or equivalent, so money isn't a huge problem. Are you comfortable paying for her flight and not splitting the hotel with her? Why or why not?

Let's assume the girl is very attractive, because otherwise you wouldn't even be considering paying for her part of the trip


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Comments (124)

Most Helpful
  • Engineer in Other
Jan 23, 2020 - 4:51pm

Depends if my wife checks the credit card bills

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  • 4
Jan 23, 2020 - 4:53pm

look, in this situation - you are an investment banker. you are one of the biggest ballers on this planet. one broad is nice but why not pay for multiple beautiful babies to come on vacation with you.

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Jan 24, 2020 - 9:33am


Commercial Real Estate Developer

  • 1
Jan 24, 2020 - 11:12am

I'm in my 20s, yeah I make good money but not like that. My ideal partner is a best friend who I also sleep with. I wouldn't pay for all that just to have my best friend go with me, so if I DO pay for it, I'm quite literally paying for the sleeping with part. Feels like a transaction to me. I want a partner not a burden

Jan 23, 2020 - 4:58pm

Do it if you have no expectations of anything in return. You want to go on a trip and you think going with her will be fun. If you can afford it then bring her along. But do it without any expectations.. you just want to have a good time and want her to come along.

Jan 24, 2020 - 9:20am

Just don't expect just because you took her on a all expenses paid vacation that she will or should have to. Go with the thinking that you just wanted her along because you would enjoy it better and you just want to have fun. Don't go thinking "ok I paid for all this so she will sleep with me, she will like me, we'll date". That will lead to disappointment and have you thinking about stuff you shouldn't during the trip. If it happens it happens, but just go have fun.

Jan 23, 2020 - 4:59pm

No - uncle sam taxes me too hard to be a sugar daddy in my 20s.

What concert costs 45 cents? 50 Cent feat. Nickelback.

  • 24
Jan 23, 2020 - 5:15pm

Obviously. You're paying to have a good time with someone you enjoy being around.

Don't overthink this stuff.

Commercial Real Estate Developer

  • 22
Jan 31, 2020 - 1:22pm

I agree, I feel that I see these questions asked all the time. Before I got engaged I paid to take my then GF (now Fiance) with me on a vacation as a surprise. If you really like/love the person and would rather go with them than anyone else then isn't the cost worth it? More fun on a trip = better value. So many people overthink now, when in reality if you see yourself with them long term taking trips is normal and assuming you have already decided that this is long term you have already accepted the pay differential for what it is and decide it does not matter to you because if you do get married you will be footing the bill often so better to get used to it now.

Jan 23, 2020 - 5:19pm

Right now when I go on business trips with my long-term girlfriend will usually tag along. She pays for her own flight/food/etc... and since I have to get a hotel room anyways it's not a huge deal (cost doesn't change if 1 or 2 people are in a room).

For real vacations, we split 50/50 right now but that will probably change once we get more serious. She makes about $80k - $90k so splitting isn't unreasonable. Sometimes I do want to do things like splurge on a ridiculous dinner...in which case I'm fine with paying since I really want to do something ridiculous but it doesn't happen often.

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  • Associate 1 in IB-M&A
Jan 23, 2020 - 5:34pm

If you have to ask this question the answer is no. Just go stag and slay some randos. If the pussy were that good you would have booked the tickets already.

Jan 26, 2020 - 9:34pm

You are so on point my friend. SB'd
OP is definitely not enjoying it.

"Be persistent and you will get, be consistent and you will keep it, be grateful and you will get more" #phuckQuotes
  • 1
Jan 23, 2020 - 5:53pm

I wouldn't mind paying for everything. Depends on how committed she thinks I am.

I don't know... Yeah. Almost definitely yes.

Jan 24, 2020 - 9:01am

Unless I have been dating her for over a year, no. Even then, I've been with my fiance for over 5 years and she still pays for her plane ticket and half the hotel room when we go on vacation. If I decide to splurge on her during the trip, or pay more for a better room for the both of us, then that's my decision. It's certainly not an expectation.

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  • 2
Jan 26, 2020 - 1:04pm

It's not about tallying up pennies. What's mine is hers. But she works just like I do so why wouldn't she pay for half of the basics (I cover the luxuries)?

  • 1
Jan 24, 2020 - 9:40am

I do this all the time. A few hundred bucks to bring a chick you have in the bag vs. going out with buddies and spending on some serious nonsense. When I am out with friends, I am easily spending a couple hundred...why not put that into a flight for $300 and have a sure thing with a hottie? Biggest mistake is going skiing though....that adds up in a hurry, especially if she sucks.

Edit: entire point I meant to write is that I just add this to my monthly entertainment budget.

  • 7
Jan 24, 2020 - 9:44am

If she's in the bag then she can pay her way. Stop trickin' on these hoes man.

  • 1
Jan 24, 2020 - 9:48am

It literally does not make a difference to me. Most of the women I fly to meet me somewhere are traveling from different cities...like I said, just add it to the entertainment budget.

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Jan 24, 2020 - 10:07am

Imagine going on your annual vacation to a dream location and NOT getting any sex... just pay it

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  • Quant in HF - Other
Jan 24, 2020 - 10:56am

If it's a genuine relationship/you're fairly serious or can see it becoming serious or whatever, then yeah no problem with that. If it's just someone you've been banging recently and want to look like the man flying someone out when in reality you don't really know their character that wel, then you're a chump tbh.

Jan 24, 2020 - 11:46am

What is a better way to get to know somebody's character? Five dates at $100 bucks a pop or one trip for $500? I think you learn a hell of a lot more traveling with somebody. Speeds up the process and you can get a lot more done. Its hella fun too.

  • Quant in HF - Other
Jan 25, 2020 - 6:33am

I think my problem with that is you don't know at that point if she just likes the idea of a free trip and doesn't really give a shit about you. Not to sound like some reddit red pill dude or anything, but I'd be kinda pissed off if that turned out to be the case.

Jan 24, 2020 - 1:08pm

if you're asking, it's because you like a chick but you're unsure if you should pay. get her to have some skin in the game. she can book her own flight and maybe a meal or two, but yeah if you're caking, pay for the rest

if she wants to go on vacation with you it's because she likes you. don't overthink it like jerry did when that brunette invited him to the poconos

Jan 24, 2020 - 1:25pm

So i guess the other items you mentioned in the previous post (gaming PC, wardrobe upgrade) aren't quite as high on your list as this little slay-cation. Glad you drummed up this little hypothetical here just to let us all know your GF is very attractive--nice-- I'll play along.

We can also probly assume since you roped in "hook up buddy" here, that things aren't that serious. Nonetheless, i would say go for it. Just know that this little get-away isn't going to change the transactional nature of your relationship or make you feel anymore comfortable truly investing in yourself.

  • Analyst 2 in RE - Comm
Jan 24, 2020 - 1:58pm

I lol'd - I enjoy posting topics that generate lively discussion. I got the feeling this topic would, and it did

How many comments would I get it if I made a separate thread titled "Would you spend $2,000 on a hobby of yours that you're passionate about?" Probably zero because that's boring and everyone would have the same opinion on it

Ultimately I'm gonna do whatever I feel is right, but it's fun to see how other people feel. Both sides have had solid arguments for why it is / isn't a good idea

Jan 24, 2020 - 2:18pm

It's a worthy topic, I'll give you that.

And i'm sure you won't mind spending the majority of your one-or-two annual vacay's snapping candid pics of her all over some shit-hole island in the tropics--just so she can flex them as marketing material to every d-bag named Preston in the East Village, who lays better pipe than you.

Skip the trip. Take her to a nice dinner.

  • Analyst 2 in CorpDev
Jan 24, 2020 - 3:20pm

Absolutely not. It's 2020, unless I'm a 50 yo sugar daddy trying to snag a 20 something model for a week away, we are always splitting the bill. You just provide dick and charisma my man.

Jan 24, 2020 - 4:47pm
Analyst 2 in CorpDev:

Absolutely not. It's 2020, unless I'm a 50 yo sugar daddy trying to snag a 20 something model for a week away, we are always splitting the bill. You just provide dick and charisma my man.

Yeah. Men remain insecure in 2020 while women are flying after finding themselves through feminism.

Don't use money to make up for what you lack. Have some balls. It's plenty of women out there who can pay their own way.

Jan 24, 2020 - 3:22pm

Depends how much the trip is and how you're looking at it. If you're seeing it in the eyes of paying for a cute friend to tag along with you simply because you got it like that, I say yes.
If you're expecting something out of it, or doing it because you want to signal to her she's special, you're on some sucker shit and it's a big hell no.

Jan 24, 2020 - 3:28pm

If she's hot and doesn't make a lot of money I'd definitely pay. We don't serve money; money serves us. What point is there in having money if you can't use it to have fun with attractive females?


  • 4
Jan 24, 2020 - 4:06pm

What if she just wants to go on the trip and not give up the goodies?

"It's okay, I'll see you on the other side"
Jan 24, 2020 - 4:44pm

A few weird answers in here...

Pretty straightforward. Are you already banging this girl? Would you rather go on the trip with this girl vs. a buddy or by yourself? Does the trip cost more than what she can comfortably afford?

If yes is the answer to all three, take her on the trip, have her pay for a portion that makes sense, and cover the rest.

You're a chump if you pay and either you haven't banged yet or you think doing so will impress her. Otherwise you are going on the trip you want to go on with the person you want and paying a little extra to make that happen and see if she's a good time to travel with. If you don't have a good enough time with her on this trip then you go with a different girl next time and you saved yourself some wasted time with the current girl. You're a chump if you are worried about what she gets out of it (discounted trip, pics, etc.). You went on the trip you wanted with who you wanted and figured out if they are cool enough to stick around longer.

Jan 24, 2020 - 9:00pm

This is a great thread, very funny responses. Ask her to chip in what she can in total (she can contribute something), so you both have no animosity/misunderstanding, and don't personally spend more than you feel comfortable spending. Because if you overspend then you'll be agitated and give off negative vibes, which isn't fair or pleasant for anyone. Work it out, go, and have fun.

Jan 24, 2020 - 9:51pm

Interesting responses. If I was in this situation I would absolutely pay. I already do this with the wife and kids right now. So, way more expensive than just an extra flight ticket. And when you're married with kids, sex is not guaranteed.

Feb 5, 2020 - 4:12pm

Something is guaranteed, that it won't happen, or maybe, just maybe you might get lucky and for a short 2 minutes before one of the kid wakes up you might get a chance to cuddle, but you'll both be so tired anyways that it won't be as enjoyable as when you were in your twenties enjoying casual sex drunk on a random beach in Thailand.

To OP - when I was a young banker I paid a girl to come for the weekend. We shagged. It was great. It was an all expense paid trip - I had met her once at a party, she lived in Stockholm and I was in London. I hadn't shagged with her, but we chatted a bit online and clearly when I tell her am paying for your trip it's not to fucking hold hands.

Why would you ever think twice about paying for a girl's vacation?

You are a dude, at the end of the day none of that equal shit is valid unless you are some pathetic fat ass with skinny jeans working at Google in marketing. Be alpha and pay, you'll thank your younger self later in life for having grabbed life by the balls. What's the point of money if you can't spend it!?

When you'll have kids like Dick and I you won't regret having paid some cash for some cute girl to have fun with.

Jan 25, 2020 - 4:46pm

female over here.

what is more important to you? is her company worth it?

a. if she can't afford it, and she is happy to stay at a lower tier hotel, then maybe you can also consider meeting half-way and staying at a less expensive hotel. sometimes, some people feel intimidated and 'embarassed' to express that they can't afford X and so end up not speaking up and spending money on things they can't afford. obv it's not on you that she may feel this way, but i think it's something u should be conscious about.
b. if it is THAT important to you, and you actually care about her, then wouldn't you want to share what you enjoy with her and subsidise her bit? if i had a bf and i knew he couldnt afford what i can afford for both of us, i would personally be more than happy to subsidise.

go alone. if you miss her then u know she's more than just a hook up buddy for u and invite her next time.

Jan 26, 2020 - 10:05am

finally, someone talking some actual sense in this thread.

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  • Associate 1 in S&T - FI
Jan 25, 2020 - 7:00pm

I think this is a great way to test out a relationship and see if you do really enjoy each others company for an extend period of time and if this person is really into you or just likes the fun stuff you plan. However there are rules to this.

  1. You drive the bus on this, you suggest it, plan it, pay for the hotel, make the dinner reservations, plan activities. You should have a decent idea of what this person likes to do

  2. You are able to drive or take public transit to whatever it is you are going to. 2-3 hours max.

  3. Skiing is the worst idea ever, unless she shreds you are going to spend most of your time waiting around.

If this girl is actually not a totally awful human being she going to offer/insist on paying for a dinner or 2. Huge red flag if she does not. Also don't mention how much anything you set up costs, it makes you should lame and cheap. There are 52 weekends in a year, losing one to something like this when it does not work out is not the end of the world.

Jan 25, 2020 - 10:15pm

Unless you are very serious about this woman (i.e. she is "the one" and you are definitely going to marry her), I would say NO WAY. Despite everything your friends/family, society, the media, etc. has conditioned you into believing, spending money on women and treating them like princesses is absolutely the wrong way to make them attracted to you. Sure, you may get some results in the short term, but in the long term you are setting yourself up for failure.

Consider the following quote from one of history's most controversial figures:

*The psyche of the great masses is not receptive to anything that is half-hearted and weak. Like the woman, whose psychic state is determined less by grounds of abstract reason than by an indefinable emotional longing for a force which will complement her nature, and who, consequently, would rather bow to a strong man than dominate a weakling, likewise the masses love a commander more than a petitioner and feel inwardly more satisfied by a doctrine, tolerating no other beside itself, than by the granting of liberalistic freedom with which, as a rule, they can do little, and are prone to feel that they have been abandoned.
Why do you suppose there are so many tattoo-clad thugs/gangsters who treat women like shit but have no trouble getting laid (and often having children out of wedlock) and the same woman (or baby mama) keep coming back to them despite being treated like shit whereas the college-educated beta male finance nerds (i.e. YOU) are, at best, going through the motions with some "girlfriend" (who will drop you the moment she finds someone better) or at worst are at home fapping to pornhub?

If anything, SHE should be the one paying for the entire vacation. Psychologically, humans have an innate proclivity to "beautify" (for lack of a better term) the things they have spent money on. It's a sunk cost fallacy, plain and simple, but humans continue to commit these errors over and over again because it's a drug - literally - the dopamine rush that people get when the occasional good thing happens to them. Why do you suppose people keep playing slot machines in the casino that are statistically designed to make them lose money in the long run? Because the dopamine rush that they get when they win $1000 is overwhelmingly powerful despite being lifetime down $5000.

The example above is apt, because to have success with women, you yourself ultimately need to become like a "drug" and the woman needs to become "addicted" to you. How do you do this?

Two things:

1) you need to be highly stimulating / exciting to the girl in some way. An imperfect comparison is "DHV" articulated years ago by Erik von Markovik et al, but it really goes beyond that, since these are in daily interactions and not just the initial encounter / when you first meet them. It is highly variable since it depends on you and the girl, but it could be something like telling them a joke that elicits genuine laughter, serenading them with a song, etc. Of course, as with anything in life (e.g. getting the job, being promoted, etc.) being physically attractive is a big advantage, but it's not a deal breaker if you are not that good looking - plenty of the aforementioned thugs/gangsters with ugly mugs who have no trouble getting laid. Of course, being in physically good shape and well-groomed are table stakes.

2) you need make this girl spend as much money on you as possible. Start with something small like getting her to pay for your gym membership. It should be a relatively simple ask, and if you get push back, tell her something like "Don't you want me to look good for you?" Alternatively, you can propose that you both get memberships together, so that you can work out together (and hence spend time together). If she still refuses to pay, dump her and move on to the next one. Work your way up to getting her to pay for more stuff. After the gym membership, a natural next step is getting her to pay for protein powder and supplements. From there, you are only limited by your imagination. Get her to pay for your cell phone (
So I can text you, baby"). Your netflix subscription ("So we can chill together, baby"). Get her to pay for (or cook) all meals that you have together. Whatever it may be, make her understand that she should be grateful that you are spending time with her, so her paying for this stuff is a very small price to pay in exchange for the time and attention you are giving her. Eventually, you will want to move in with her and get an extra key so you can come and go as you please. This has two benefits - 1) if you are living at her place, you don't really need your own place anymore, so you can save A LOT of money since rent is typically going to be your highest monthly expense. 2) make her conscious of the fact that by having a spare key, she will have to keep her attitude in check, because if she bitches at you or gets into an argument with you, there is always the risk lingering in the back of her mind that you will go to her apartment when she's not there and trash it. Over time, the sunk cost grows larger and larger as will her dependency on you.

Naturally, society will not condone such behavior and they will not hesitate to call you a "mooch," "bum," "loser" or whatever insult, but screw them. Ignore the sheeple and their conventional thinking. Laugh at them in pity while you get laid whenever you wish while keeping your living costs virtually zero. You will have doubts at first and it might be very uncomfortable - that is what decades of societal conditioning will do to you - but if you can breakthrough mentally, you will change your life. If you take away nothing else from this post, just remember that conventional thinking leads to conventional results.

  • Analyst 2 in RE - Comm
Jan 26, 2020 - 9:20am

Stopped reading when I got to "beta male"... I'm pleasantly surprised it took this long for someone like you to show up in this thread.

I've noticed some people respond to posts with regard to their own insecurities. For example, on another thread I asked how to get more comfortable spending money on things I want (eg a $2,000 gaming computer). Someone responded in bold letters: "DO NOT SPEND ON MATERIAL THINGS JUST TO IMPRESS YOUR FRIENDS OR LOOK COOL".

The thing is, a gaming PC is a solitary hobby. It sits in my bedroom, under a desk, and I don't tell people about it cause I don't want them to know I spent that much on gaming. It's the exact opposite of something you spend money on to look cool. So why did the guy answer in that fashion? He probably struggled (or currently struggles) with wasting money on material things to impress people. Sure enough, he admitted to having 100k worth of watches...

In this case, you assume I'm doing this because I care about this girl, I want her to like me, and I'm willing to drop big money in an attempt to make that happen. In reality, the girl in question is someone I like to hook up with. I don't want a future with her. I want a chill weekend on the beach with a hot girl.

I feel bad for someone that has such a hard time getting laid, that they're willing to do a ton of research on "how alpha males have sex even when they're ugly". It's pathetic yet hilarious at the same time.

I won't spend anymore time responding to your posts so save your energy

Jan 26, 2020 - 10:32am

Not specific to the GF argument but I have a good friend who makes very little money and when I know cost might be the difference between her hanging out or not I will chip in.

Obviously a restaurant is very different from a flight/hotel but if you are serious about this person and really want to have a certain experience, why not?

Jan 27, 2020 - 11:22am

Would do it. She can cover her plane ticket, but most hotel bedrooms are for two people anyways so yeah, would do it. She'd have to be an extremely serious girlfriend or fiancee or wife though.

Jan 29, 2020 - 12:51am

Very slippery slope my friend. The fact that you and this girl haven't had the money talk means it's really early in this "relationship" and you barely know each other.
Once you pay for everything and don't set your boundaries early on, she'll just think you're just an open wallet.
She needs to contribute to something; if you pay for the flights, get her to chip in for the hotel or at least have her buy the food there. Something. Otherwise you're just some schmuck buying her time like every other guy who's tried to lock her down. Don't think with your dick. Rise above. Chase money.

  • 1
Jan 29, 2020 - 8:53am

i would like to think she would want to chip in in some sort of way, without having u to ask. otherwise–

i mean some guys are ok knowing theyre paying for everything in exchange for a hot girl's company [hook-up scenario], knowing fully well it will be expensive. and some girls are comfortable with someone paying for everything. as long as ure both on the same page and having fun then i dont see a proooooob. just dont go and end up getting pissed ure paying for everything cuz that would ruin ur vacation and i mean... u made ur own bed.

have fun!!

  • Analyst 2 in CorpFin
Jan 30, 2020 - 1:21pm

Assuming she's a real girlfriend / has been around for a little bit or its a good hook up buddy, yes.

It's not framed as "I'm lavishing gifts and money on you". Its framed as "We're partners in this, and I want you along. I'm more able to pay, you wouldn't do this with me if I wasn't paying, and I want to do this with you, so it's my cost".

Jan 30, 2020 - 1:56pm

Going to reverse the gender here. My BF is unemployed and I've always made more than him. I personally would pay for the flights, but we would need to split everything else... If we were married it would be different.

Greed is Good!
Jan 31, 2020 - 1:38am

If it's just a hookup and a good time....fine. Maybe.

There are so many problems with vacations with women. Unless you found a unicorn, she'll take a bunch of shit that you'll carry and finally get to the hotel. You'll end up in a bar that you would have been in anyways back home. There are a million things to judge you on or give you a load of shit about.

If she's that cool, you'd already have a better time getting out of the city or doing something unique.

I'm a little biased living in So.Cal. where it's a vacation nearly everyday, but it's usually a bad idea.

Jan 31, 2020 - 10:55am

I have a few friends who aren't making great money yet or are currently in med/law school on student budgets and I've paid for them to come with me to sporting events or trips before. Why? Because I enjoy their company and rather them come with me. The time and experiences spent with them is more important to me than the money.

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