Breakup Before Vacation

Breakup Before Vacation

A couple years ago my friend “Sandra” bought a certificate for a vacation package as a present for her boyfriend of several years. A few months later they broke up, and she realized she would need to use the certificate by the end of the year.

Planning the Dream Vacation
Miami Beach SilhouettesAfter months of casual dating she met an amazing, unique woman unlike anyone she had ever dated and started dating her for a few months. This was her first relationship after months of casual dating and she wanted to make it work this time. She asked her girlfriend if she would go on a vacation with her using the expiring vacation package and she agreed. Sandra reserved flights, a cruise and a hotel and started dreaming of taking a special trip to Hawaii with her new girlfriend. A couple months later, all the reasons that made her unlike anyone she had ever dated came to the surface, and they broke up.

From Two to Three
Sandra told me about this Christmas to New Years vacation in November, and I asked if I could join her instead. Her face lit up and we started looking at flights and I asked my husband if he would join us. She couldn’t change the names on the flight, but she did get a partial refund and made some other changes that could accommodate having two other people. We hadn’t taken many American vacations with hotels as adults, and I was excited to make this happen.

From Three to a Reunion
We scoured the internet for affordable prices, and found out the cruise portion was cancelled and therefor refundable. We messaged about Airbnb options while we were both at work and soon we had our first trip together! Meanwhile, Sandra persuaded her friend visiting family on another island to take a short detour to meet up with us and she discovered another newer friend from our hometown of San Francisco had scheduled a birthday dinner in Hawaii during our visit. This vacation was changing from a two person retreat for two different ex-partners who were not ultimately good matches for Sandra into a reunion and gathering for her friends from different branches of her life!

The reasons that push couples to fight and sometimes break up would have been under the surface the whole time.

Self-Discovery, Not Romance
Sandra taught me about deal-saving sites like and, and I brought her to her first Couchsurfing party in Hawaii. I met her college friends and she showed me her favorite karaoke bars she had visited with her ex-boyfriend, the original intended recipient of this gift. We saw new sides of each other and made New Year’s Resolutions together. While a romantic trip to Hawaii with one of her ex-partners would have had it’s charm, the reasons that push couples to fight and sometimes break up would have been under the surface the whole time. In the end, I’m glad that Sandra had the courage to end these relationships when she did and that she had the heart to share this vacation with new friends and non-lovers.

So what can we learn about moving forward from a frustrating relationship or breakup and vacations?

Four Tips for Thriving on Vacation After Your Breakup

  1. Don’t let money spent keep you in a relationship that doesn’t work. There is always a better way.
  2. Speak up about your desire for companionship on your trip. Romance is only one form of satisfying companionship on a trip.
  3. Be generous and courageous in asking new friends to join your trip.
  4. Be creative, assertive and flexible in changing your vacation plans to make them fit your current lifestyle.

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