I have lost luggage, I have slept on airport floors and in budget backpacker hostels, I have weathered flight cancellations, food poisoning and days of unbroken rain. Yet my worst-ever holiday, a weekend away with my boyfriend, went entirely to plan.

We had been seeing each other for a few months, and this was our first trip together. But removed from our usual contexts (in bed, or watching TV, or watching TV in bed), we realised too late that we had nothing to say to each other. At one point we parked our rental car and just sat there, passing the time until we could go home and eventually break up.

Anecdotally, this is not uncommon. The first trip away together can be make or break, either by highlighting incompatibilities it was easy to gloss over at home, or by putting your new relationship under such strain it is unable to recover. Asked for advice for surviving couple holidays, more than one person responded: “Separate trips.”

If you are planning on getting away with your new partner, you could approach it as a useful stress test, an Amazing Race-style challenge by which your future potential as a couple will be measured – or you could take these steps to increase your odds of returning in a relationship.

Do your groundwork

A holiday can be a great way to get to know each other. But one person’s idea of unwinding might be posting beachside “hot dogs or legs?” photos while another’s is informed by DangerousRoads.org (“the world’s most spectacular roads”). So get a sense of how your new partner likes to spend their time off before you commit to doing it with them.

Don’t fear a mishap, such as getting lost; at least you’ll have something to talk about. Photograph: itsskin/Getty Images

The relationship therapist Kate Moyle says the first holiday as a couple can reveal clashing agendas before you have even left the house, giving the example of those two types of people: “Getting to the airport with hours to spare, versus when check-in closes.

“If you know that, as a couple, you already have these differences, then talk about them before and have a rough idea of what you want to do, so that you are both able to get what you want or need.”

But the freelance writer Fernanda Fain-Binda suggests taking charge of one task yourself. “Pack your bag in private. They just don’t understand!”

Manage expectations

Sarah Stein Lubrano, who teaches love courses at the School of Life, says some people expect holidays and relationships to be fun all the time. “But pretty much nothing is fun all the time – we would gently say lower your expectations in that area.”

“Developing stoicism” and mentally preparing yourself for the worst-case scenario (“we call it pre-meditation”) can actually help you in the event, she says. “If you expect things to go wrong, you might be a little less angry at your partner if they do.”

The Guardian writer Tim Dowling looks at it another way. “The biggest worry when you first holiday as a couple is that you’ll run out of things to say after 24 hours, so disaster can be a bit of lifeline on that front.”

His first holiday alone with his now wife was their honeymoon. (“My first thought was: ‘Why not invite along six or seven other people?’”). They ran out of money, got frequently lost and “made the dire mistake of hiring a boat with two oars instead of an engine”. “As a result,” he says, “there was always something to discuss.”

Split the planning

Choose the destination together, though you can make life easier for yourself by picking a country that you feel confident navigating. This may not be the time to test your schoolgirl (or boy) French, unless you were a very precocious schoolgirl (or boy). Pauline Morning, the head of customer experience at Thomas Cook UK, suggests somewhere neither of you to have been before, so you can explore it together. “And probably best to avoid hotels or cities you went to with an ex – there’s nothing worse than hearing all about what your partner did the last time they were there with someone else.”

The itinerary should be a joint effort. Photograph: izusek/Getty Images

The itinerary should also be a joint effort. If one person takes charge, it is bound to cause resentment, whether the beneficiary likes the outcome (and is free to enjoy the results, with none of the work) or not (and takes issue with a half-day set aside for touring derelict Olympic stadiums).

Split the planning between you, bearing in mind each of your interests and strengths. Some people have no head for admin, for example. And don’t try to pack too much in. “Don’t overstuff your itinerary,” says Nicole McFarlane, who has been holidaying with her husband for more than 20 years. She suggests working to one activity a day, of up to three hours in duration, then keeping the rest free for incidental sightseeing.

That extends to not attempting too many moves, of either location or accommodation. Jared Wells (credentials: 15-year marriage, two children) is in favour of simplicity: “Making your own entertainment and adventure, not relying on some inclusive stuff-your-guts and karaoke … Plenty of booze is always good, too.”

Talk money

Keep a running tally of who has spent what and be explicit about when you’ll settle up. It is also sensible, if undeniably unsexy, to discuss ahead of time how you will split the costs in the event that one of you drives the hire car off one of those dangerous roads, or any other catastrophic scenario. Call it a holiday prenup.

Prioritise reliable transport and comfortable accommodation

Trains are a good transport choice. Photograph: Mixmike/Getty Images

Do what you can to minimise stress. This means not flying Ryanair – all those queues and petty restrictions will extinguish even the most vibrant sparks – or hiring a car if you are not a confident driver. You do not want to find yourself in a situation where your partner decides he would rather risk a huge fine or a year in French prison for driving without a licence than have you behind the wheel. Trust me.

Trains – which are typically on time, permissive of day-drinking and bring endless stimulation straight to your window lest the conversation dry up – are a good option. Bikes are also romantic, though more so in theory than reality.

Do not, whatever you do, book a boat. It is not romantic. It is an unreliable toilet surrounded by water. The same goes for campervans, which – though certainly more comfortable than camping – are unreliable toilets on wheels.

Do not go camping.

Be a bit more on it than usual

If you forget your phone charger while on holiday alone, it’s certainly frustrating, but you are inconveniencing only yourself. When you are with a new partner, the stakes are higher. You may, remember, still be under assessment. So plan ahead. Pack properly. Print out your tickets and reservation details, even if they are on your phone. You do not want to spend 35 minutes facing your patient partner, on the phone to Airbnb, because you can’t get in to your account because you don’t know your password, because you signed up with your old work email and you won’t get the texted log-in code because you left your usual sim card at home, meaning you can’t access the address of the apartment where you are expected by your host in 45 minutes. Hypothetically speaking.

Pack at least one game …

Run out of conversation? There’s always Uno. Photograph: Ole Mathisen/Alamy Stock Photo/Alamy Stock Photo

It is hard to imagine in the first flushes of romance, but you may run out of things to talk about. In that case, a shared, low-stakes activity such as a quiz book or Uno – something with which you can easily while away a couple of beers or a flight delay – can be a boon.

A word of warning: if you are a very competitive person, this might put your relationship under further strain. But you would still probably prefer Monopoly Deal to Lubrano’s suggestion of the School of Life’s conversation-prompt kits, designed to make your conversations meaningful.

… and books

The idea of spending every hour together may appeal in the world you left behind, where you spend at least eight hours a day apart; in reality, it can become oppressive. Yet asking for “some space” on what’s supposed to be your romantic getaway can be interpreted as a slight.

It’s “a little bit of a taboo” to want to spend time apart from your partner, agrees Lubrano – but it shouldn’t be. “We expect that our partner should be the perfect companion for every activity, but it’s very healthy thing to say: ‘This is my day; I’m going to do what I want to do.’”

But if you fear hurt feelings, you can achieve the same effect by escaping in plain sight into a world of another’s creation – and somehow, books are often more acceptable than putting in earphones.

Play to your strengths

Prioritise your base needs – no, not sex. The T-shirt slogan is true: some people really do need caffeine first thing to function. Others are susceptible to rage when hungry. If your partner is irritable or stressed, it may be because they are in need of food or sleep, not because you have driven the wrong way round a roundabout again. Do what you can to boost your resilience, especially if you are the one being driven.

And play to your strengths. Going away together is also an opportunity to “show your partner how you like to run things”, says Moyle. Some people love to dispute hotel charges, or haggle taxi fares; others are more comfortable taking a backseat role. Difficulties arise when, by circumstance or hubris, we assume roles we don’t naturally fit. “It’s nice sharing new experiences as a couple,” says Dowling, “but some tasks require an actual leader: the one with the sense of direction, the one who speaks the language, the one with basic first-aid training. Sometimes, it’s more helpful to stand back.”

Don’t talk about the future of your relationship until you’re back home

You still have to get home … and you booked Ryanair, didn’t you?