Should you pay back your boyfriend for vacation before breaking up?

Happy Friday, everyone! With life getting back to normal, I hope you all have plans for a fun vacation or staycation this summer! I can’t wait to get out of town for a few days after spending the last 16 months at home.

On that note, here’s a tricky question I answered from a reader this week. Her boyfriend booked a vacation for the two of them and insisted on paying for it. But he’s been kind of a jerk lately and she no longer wants to go. So her question was: Should she pay him half for the vacation before ending things?…my-half-of-vacation/

I think that yes, she should pay for her half if it wouldn’t cause her hardship. Honestly, I’m less concerned about him, but I think paying her half could put her mind at ease a bit. But I’m curious to hear what all of you think. Should she pay him back before breaking things off?


Oof. Tricky, tricky.

If she’s unhappy with the current situation, I definitely think it’s time to walk. In terms of paying for the trip, I’m on the fence!

Because she’s not going on the trip, I’m struggling to understand why she should pay. For me, it’s more of the etiquette around gift giving. I really think people have to be clear whether or not a gift is truly a gift, or if there’s some expectation to receive something monetary in return.

It really does sound like they likely weren’t on the same page or avoided honest dialogue about money and expectations, which I think is a no-no particularly for an almost year-long relationship.

@davis.quay @kellyfromkeene @irishnanny @rick.campbell @amypatt curious to hear what y’all think about this one! Feel free to disagree, lol! ?


Definitely pay him back, and get him out of your life for good. If he’s being “sort of a jerk” now, why leave open a tie from him to you? Pay the man.


Definitely pay him back. And put him in the rearview mirror!!

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All along it has been a history of gifts, gifts, gifts…and this seems to be no exception. It would also depend on the price of this vacation and if it is refundable or non-refundable as far as reservations. That’s where the stake of the money would be and what he can do to remedy any loss. I would do the break up, let the pieces fall where they may and go from there, he may be out of pocket very little. If not, then you would need to keep all texts to document commitments and conversations, nothing verbal is acceptable. That would be a “he said, she said”. Let him prove it was not a gift. Did you agree to pay for anything?


i think she should and then move on, she agreed when he made the plans and now its a no go, just my thought

After reading @redcatcec post I’m rethinking my response a little. If he can cancel and get a refund she should not be liable for any expenses but I think she needs to speak to him and discuss this. I still say he should be history because he insisted on paying for everything and then complained about it. If a person invites someone to an event (dinner, movie, etc.) and says they will pay for it, they should not complain later that they have to pay for everything. That goes for anyone, not just dating behavior.

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No, she should not have to pay him back for the vacation. She did not go on the vacation, and it was a gift. If he wants any payment, that just perpetuates his jerk behavior.

This reminds me of when an ex-bf and I split up and I moved out. His arrogance made me pay him for any furniture I wanted to bring with me. I wanted to keep the vintage guest bedroom furniture found at an estate sale, so I paid him back because it was cheaper than looking for new furniture for my apartment at the time. Other men I know were kind enough to let their exes keep any furniture for free.

I think the question is should she pay him for half the vacation and I agree that she is not obligated to but to ease her own mind she wants to be fair, even though he is not playing fair by any means. She has to know herself because I know if it were me, I would say not to pay him back but later on I would be second guessing myself and hashing it over and over in my mind if I did the right thing or just acted in anger. Just my thought.

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I know how good it feels to pay my own way after relying on a man/anyone- and I don’t mean that in a negative way! I mean, I have always earned significantly less (hello Human Services) and it feels good to cover my expenses even if I have to save up for them.

ANYWAY… I would offer to cover whatever I would be comfortably able to do. Not going broke, but just enough to ease my ‘conscience’. Then I can walk away with no guilt, and not look back.

My opinion, for what its worth.

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Definitely an interesting situation.

I would say you certainly shouldn’t necessarily feel obligated to pay it back as it was a gift after all.

However, if you are cutting ties and would rather that person not be a part of your life anymore, it might make sense to pay it back if it means it won’t give that person something to hold over your head in the future.

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I think your advice to her was spot on, Dear Penny. If monetary gifts and money are his language, then that’s the best way to respond to ending the relationship and be clear it’s over. I’d have to handle it that way for my own conscience if he paid for everything in the relationship, even over objections. It’s not really about him, it’s about how she will feel about herself after cutting him out of her life.


My brother and I have both been on the other side of this coin. My brother for a honeymoon cruise. He simply paid $60.00 to have the ticket changed to someone else name. Me, I still wanted to go on the trip to the ocean, so, I took my ex-girlfriend’s good friend. instead. WE had a great time and even sent her pictures! Well worth the expense!


I’m going to weigh in again and say that I asked my husband (an preface that with saying he is not the most generous person around) and he said that the boyfriend paid for the trip as a gift so she is not obligated to pay him back. I’m also glad to hear about alternatives to the question. The boyfriend should look into those possibilities if he can’t get a refund.


She should not reimburse him for the vacation. In case I misread your article, It said he booked the vacation, I did not see anything saying that she was involved with the booking or any input on the vacation. So it is his problem to have to get a refund or name change on said tickets if he chooses to take someone else.

P.S. Did he already pay for everything ? Or he needs to pay by a certain date…ie…August 21st.2021 ?!? Whenever I book a flight/vacation, it’s (website) says I need to pay in full within a certain number of days before departure.

Just my thoughts.