Couples Vacation: When is the right time to go?: Guest Post

Enjoy this guest post from Lilly Star where she explores the ins and outs of going on a couples vacation and whether or not it’s a good idea to go early on.

We were headed to Belize. The relationship had been going well, even though he lived in New York City and lived in Los Angeles. Traveling felt like part of the relationship so it was just a few nights of hotels, and an extra flight. What could go

First there was the Hurricane that flooded much of Belize, making roads impassable. That wasn’t itself an issue, but I’d already put down a deposit on a resort for $300 and though the hurricane and on-the-ground reports made us nervous about going, the local hotels refused to return the deposit. Ultimately he decided that it was too treacherous a trip and so we changed our flights and our itinerary to the Dominican Republic, a direct fve-hour flight for him — a nine-hour multi-connection disaster for me.

With my frustrations building and my money and time disappearing, I started to realize that at only seven months of dating, maybe this trip was too soon.

When to go on a couples vacation is going to vary wildly on the persons in the relationship, but there are certain stresses all couples should feel confident in overcoming before they hop on a place or make an ill-advised hotel room deposit.

Be sure you understand the planning for a vacation together is stressful, the trip itself is expensive, and you’ll be spending almost every minute together for more than a week (possibly two!). All these factors can lead to stress and if you don’t have the communication skills to navigate some of the more stressful details then you could be faced with an enormously catastrophic trip with a partner.

My trip ended fine, but it was obvious to me that he wasn’t respecting my time and money as much as I’d like. We hadn’t worked on details, instead I’d let him manage our hotels and activities even as I paid for half (something I believed I should do). He was a good guy, but living at a distance and then spending the most time we ever spent together in a place that was meant to be de-stressing (but proved to be frazzling) was the recipe for our demise.

Just keep in mind that the man you are traveling with is going to show you his complete self. For some women that’s exactly what is needed for their relationship, others that are too early in the relationship might be turned off by that level of unencumbered access.

If you do decide to go remember to try and have fun, relax and really open up to each other, because despite all the build up and the expectations all you should be aiming to do is relax and connect!

Lilly Star is the lead female voice at, Lilly is a professional advice-giver with experiences in dating men of all types, including the good ones that got away.  Lily’s work can be read on dating blogs for both men and women.

Your Sister in Dating Bliss,

Single Dating Diva

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