First holiday together as a couple? Relationship expert reveals dos and don’ts

Going on a holiday together is a huge milestone for any couple.

For many, it can be a sign that they want to take their relationship to the next level if they manage to survive the vacation together.

That also makes the holiday a double-edged sword. It may be the first time couples see each other outside their comfort zone while they spend more time than usual in each other’s company.

In situations like this, tensions can rise and fights can break out, which is why couples should keep some key pointers in mind when planning a first holiday together.

Speaking to 2Chill, relationship expert, Neil Wilkie said: “Going away together is one of the big milestones in any relationship, and is a natural step forward.



Relationship expert Neil Wilkie shares his top tips for couple’s heading away for the first time

“It takes you both out of your ‘safe’ space and puts you both in a fresh environment where you can have time together exploring each other and new places.

“It will also enable you to get a different perspective on your partner and see how they cope with different experiences and, in particular, it gives the time and the space to see if your connection grows.”

The psychotherapist author of The Relationship Paradigm has put together a list of points to consider if you’re considering a holiday:

Understand whether it’s the right time

First of all, make sure it’s the right time for you to take that step because even if you’re both heading in the same direction, it’s likely you’ll be moving at different speeds.



A weekend away could prove make or break for a relationship
A weekend away could prove make or break for a relationship

He said: “A spreadsheet of the pros and cons will not help, nor will advice from your family or friends. Trust your intuition. If your heart and gut feels that this is the right time, then go for it.

“If you are feeling excited and nervous, that is a great sign. But if you are dreading it, then ask yourself why. If your partner is pushing you and you are feeling that this is too soon, tell them and go at a pace that you are comfortable with.”

Take the pressure off

The idea of being with each other all day every day, even for a relatively short period, might feel considerable, but ‘how big a step will going away together be?’

Wilkie said: “If you have already slept together then it will be less momentous than seeing each other naked for the first time.



If you are feeling excited and nervous, that is a great sign
If you are feeling excited and nervous, that is a great sign

“It is important to try and just relax and see what unfolds. This is a few days, not a life sentence. If it doesn’t work out, then it’ll be better discovering this sooner rather than later.”

Plan a little

It can be tempting to over romanticise how you envision the trip panning out so it’s worth taking a moment to consider the practicalities ahead of the break, so as to ‘maximise the pleasant surprises and minimise the shocks’.

Before you go, he suggests having a conversation to clarify:

-What would you both like to get from the break?

-What are the sleeping arrangements? Will you be sharing a bed or have separate rooms?



It's best to plan ahead of the trip
It’s best to plan ahead of the trip

-Who is paying or are you sharing the costs?

-Is there anything that is not acceptable to either of you?

-What fun things would each of you like to do?

-What clothing is needed? Are you talking posh restaurants, or climbing the cliffs?

Be aware issues might arise

Try as you might to be relaxed about the trip, it’s inevitable, you’re going to feel the pressure of wanting it to go perfectly, and that if it doesn’t, it’s a sign that the relationship is doomed.

Wilkie said: “This creates unrealistic expectations and a focus on the negatives and disappointments.
“Try instead going with the flow and enjoy being in the moment.”



It is important to try and just relax and see what unfolds
It is important to try and just relax and see what unfolds

The most common issues that arise are:

Sex: What happens if it is not the perfect occasion.

Lies: Finding that they have not been honest with you. Maybe not that they have a wife and three children or wear a toupee – there may have been things said that are not quite true.

Bad habits: Discovering things you don’t like about your partner. Remember you are both imperfect humans and the airbrushed avatar has been left behind.

Differing tastes: Realising you have different tastes in food, music and activities. These do not make you incompatible, just different.

Life happens: Perfectly formed plans may fall apart because of weather, transport or many other reasons.

Top tip: There will be silences as you cannot both talk 24/7. Enjoy the silence and do not try and fill it. It is a great opportunity to practice your listening skills and discover how good a listener they are.

Facing reality

So, you’ve got through the weekend but you’re more deflated than elated by the experience, what should you do – keep calm and carry on, or wave goodbye to the burgeoning relationship?

“Treat this as a journey where you have been able to find out more about each other and discover if you can be at ease with each other,” says Wilkie.

“If it has been a disappointment, ask yourself whether that’s because of external factors such as the hotel, place, weather. If so, then choose somewhere better for the next time.

“If it was down to internal factors, such as stage fright or the two of you not getting on as well as you had hoped, then ask each other the question, what would you like to have happened? Then decide if you want to have another go or call it a day.”

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