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An aerial view of Larissa, Greece
Larissa, Greece.
  • For Love & Money is a biweekly column from Insider answering your relationship and money questions.
  • This week, a reader's best friend invited them on a vacation after a breakup ruined her original plans.
  • The reader can't pay, but feels bad leaving their friend on the hook — and our columnist has advice.
  • Got a question for our columnist? Write to For Love & Money using this Google form.

Dear For Love & Money,

My best friend finally broke up with her awful boyfriend — one month before their big summer vacation to Greece. After they broke up, she looked into refunds, but there's no way she's getting her money back. Instead, she invited me to take his place. Of course, I said yes!

The trip is two weeks away, and she recently "let me know" how much my half of the trip would cost. Honestly, I planned to cover her meals and a couple of excursions but didn't expect her to ask me to pay for her ex-boyfriend's portion of the trip. Should I back out of the trip completely? Or try to find a middle ground with my friend?

Sincerely,

Too Poor to be Spontaneous

Dear Too Poor,

Your problem is simple. You and your friend have miscommunicated. But as simple as the problem may be, the solution will be tricky because, as with most misunderstandings, you likely both feel that your perception was the clear implication all along.

There are two ways to approach this. One, you can come up with an excuse and back out of the trip. Or, two, you can be honest with your friend and tell her you misunderstood the initial invitation.

Both options will create an awkward conversation at best and a full-blown falling-out at worst.

But let's set aside potential outcomes. Your best friend recently ended her relationship with a man she was serious enough about to plan a summer vacation with. She is heartbroken and now facing a difficult financial dilemma.

See Insider's picks for the best travel insurance companies that cover trip cancellations »

Yes, she knew about this trip when she chose to end her relationship, so it's her cost to swallow. However, you were no fan of this "awful boyfriend," so I doubt you want to see her punished for dumping him. And if you take the first option and back out of the trip, your heartbroken friend will be left without recourse. I don't know the circumstances of her breakup, but my experience with friends in toxic relationships tells me there's a chance this trip might be all the impetus she needs to call up the awful ex and reconnect.

However, none of this means you can fit the costs of this trip into your budget as a kind gesture to your friend. It just means that the right thing to do isn't to back out without an explanation but to take option two and be honest about your misunderstanding. Notice I say, "Your misunderstanding." This isn't because I am certain your friend was perfectly clear and this dilemma is your mistake. It's because there is nothing to gain from casting blame over how clear she was (or wasn't) in her original invitation.

Also, be honest about your financial situation. Talking about money can be awkward, and admitting you can't afford a trip that she can afford might be embarrassing for you. But remember that you have nothing to be embarrassed or awkward about in this situation. You are trying to do your friend a favor, and she had months to prepare and save for this trip; you have a matter of days.

I can't afford my friends' expensive lifestyle »

That said, you can approach the issue by acknowledging the awkwardness by saying something like, "Hey, this is embarrassing to admit, but I misunderstood your invitation when I agreed to go. I would still love to go with you and alleviate some of the costs, but I don't have enough money to pay for half the trip on such short notice. I understand if you need to find someone who can cover your ex's half instead."

If she still wants to make it work for you to go, you can try and reach a mutually agreeable financial arrangement. You pay for all the meals and excursions. Maybe you can give her some airline miles if you have any, instead of paying for a plane ticket. Perhaps you can cover half of the living accommodations, but you can't pay to get there.

Another way you could help your friend, which won't cost you thousands of dollars, is to help her find a traveling companion who can afford to pay half.

My friend owes me money but keeps dodging me. What do I do? »

An overseas trip meant for a serious boyfriend is likely very intimate — one-bedroom accommodations, candlelit dinners on the beach, private cabanas — there's a range of options for romantic couples that may be uncomfortable in platonic relationships. It makes sense that your friend immediately thought of swapping a boyfriend out for a bestie who won't cringe over a couple's massage.

That means it will be complicated for her to try and come up with another travel companion who has the money, the time off work on such short notice, and a passport, and who won't make the experience one big, prolonged awkward moment.

Offer to help her find that person, or if that's impossible with such a tight turnaround, empower her to go alone and use this time to heal from her breakup.

I agreed to be a bridesmaid — but I didn't realize it would cost so much »

Solo travel can be a rewarding experience, and as expensive as it is to pay double what a trip would cost alone, you might offer your friend a new perspective. She isn't paying for two people, but going alone, she is paying for an incredible experience, to get to know herself better, and to be free of someone who didn't fit into her life. From that view, she is more than getting value for her money.

If she does go alone, it would be a kind gesture to let her know you would still like to pay for some of her meals and excursions while she's there.

No matter what you decide, I hope you decide on it together with an honest and mutually appreciative conversation. Because you are best friends, and that's what best friends do.

Rooting for you both,

For Love & Money

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