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


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.


A second year investment banking analyst isn't a lowlife criminal...



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.


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

Don't overthink this stuff.

Commercial Real Estate Developer

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.


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.


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

She pays what she can reasonably afford and you pay more because the extra is on you. So you get the full hotel but she gets her flight or if that’s still too much then pay it all but let her get a dinner or two when you’re there. Whatever works.


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.


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.


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.


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.


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.


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


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.


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


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.


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.

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.


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.


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.