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Advice

Hawaii vacation or a summer wedding in Homer: My boyfriend and I can’t stop fighting over which to skip

  • Author: Wayne and Wanda
  • Updated: July 20
  • Published July 20

Dear Wayne and Wanda,

I am amid a huge fight with my boyfriend, and I need some advice. “Chad” and I are in our mid-20s and have been together a year. We’ve taken some trips around Alaska and went once to Seattle but we’ve never been on a big trip together and we have been planning a vacation to Hawaii at the end of August. Neither of us have ever been and we’ve spent lots of time planning the trip, including picking out a hotel that came highly recommended. And we’ve reserved a few things — like a waterfall tour, an ATV ride, a dinner cruise — but nothing is paid for yet, everything is refundable. The only exception are plane tickets I think, but the money would just sit in our accounts until we book something again.

The reason I’m mentioning all that is this past week, my very good friend “Anne” announced she’s getting married — in August, in Homer. The same weekend we’re supposed to be gone. It’s short notice to say the least but Anne’s fiancé is getting transferred to a new job which means they’re moving and they want to do it before they leave. Anne wants me to be a bridesmaid.

Chad does not understand why I want to cancel our trip to be in this wedding and be there for Anne. He says Anne isn’t even my best friend, and as my boyfriend, he should be my priority. He isn’t wrong. Anne is a good friend, top 10 for sure, but not my very best. Still, this is her wedding. It’s a huge deal!! And she’s about to move away, probably forever. And literally all our other friends will be there. If we miss it, I will feel like we missed out on the most important social event of the summer, and for what? A long weekend in Honolulu that we could literally do any weekend of the year?

Chad is really mad that I’m telling him we should cancel. He’s refusing. He says the trip is important to him, and so it should be important to me too — more important than a wedding. What do I do? Anne needs to know ASAP whether I can be part of her bridal party.

Wanda says:

I remember my mid- and late-20s — and all the weddings. Wow, it felt like a different friend was getting married every week, and sometimes in the most inconvenient locations. Church weddings, destination weddings at remote tropical locations, weddings in people’s backyards, campground ceremonies, lodge nuptials — you name it! Sometimes the weddings conflicted with things I had already planned. Had I gone to every single one, it would have bankrupted me, and definitely used up all my vacation time.

I tried to use common sense to decide when to go and when to decline. It didn’t always work. One gal pal scheduled her wedding during my 10-year high school reunion. Both events were out of state. Well, even though I hadn’t hung out with her regularly since college, I chose her wedding; and then she called it off about a week before the ceremony. It was too late and too expensive for me to rebook to the reunion. I was left with a pair of official bridesmaid cowboy boots I would never wear, and a summer weekend full of regret. So, if we want to make this all about me, the end result of trying to be selfless was I got nothing.

I’m not saying always make it all about you. But sometimes you should put yourself first. If you drop plans every time a wedding pops up, especially super last-minute weddings during precious summer weekends, you will miss out on your own important things.

This sounds to me like a simple FOMO dilemma where you’re worried you’ll miss some special moment, some funny story, and basically be left out of all photographic evidence of one of the summer’s most fun parties. But think about what you’ll miss if you stay in Alaska: your first-ever real romantic vacation with your partner, in one of the country’s prettiest places, and an opportunity to signal to him that your relationship is your No. 1 priority and you’re completely and totally committed. What is there to think about here?

Wayne says:

Sounds like everyone is hung up on either/or, but I see it as all of the above.

Technically you aren’t cancelling anything — you’re simply proposing a postponement. And you’re right — can you go on a killer Hawaii vacation any time of the year. Like, let’s see, a few weeks later in early September? You know, when kids and families are back to the good old school-year routine, which often means cheaper airfares and accommodations, quieter beaches, rugrat-free restaurants, and fewer toddler meltdowns and water works at the waterfalls. Now that sounds romantic.

To pull this off, though, you’re going to have to do a lot of legwork and damage control ASAP. Stop fighting and start searching airfares over the six weeks after the wedding, find the best one that’s the closest match to your original plan, and reserve it. Look up that cool hotel and get that reserved for the new dates, too. Then call or email to see if you can reschedule your ATV adventure, waterfall tour, and dinner cruise. If they’re available, lock them in; if not, there are literally hundreds of options for fun and frolicking in Hawaii. In fact, book a wildcard activity to surprise your boyfriend with: Diving with the sharks! Helicopter volcano tour! A big luau! Then lay it all out for him. Same (or better) vacation, at same (or better) price, only a few weeks later. Hopefully he’ll realize that you guys can do both.

Life is crazy and plans change all the time. Sure, this vacation doesn’t have to change, but if you’re savvy and sell it, you can delay things a bit without any real damage to your relationship. Your boyfriend can show a little flexibility, you both can be a part of a wedding that’s important to you and your friends, and you both can still experience what’s hopefully the first of many amazing vacations together. Good luck.

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