From Holiday Fling to Lifelong Love

By Rosanna Stevens

Growing up, holiday romances were a delightful thing to enjoy at the time and then bask in the glory of when returning to school. As a teenager, I was always quite shy and chronically insecure amongst my friends at my all-girls boarding school. But over the summer holidays, I was free. My parents took us to incredible places all over the world, and I could be whoever I wanted to be. Or rather, I could be myself.

We pack our best selves when on holiday; a sense of adventure, a relaxed and fun demeanor, a willingness to let go and have joy take over.

The attention I got from boys was liberating when away from home with none of the anxiety over comparison with my school friends.

I remember returning from trips to destinations like The Bahamas and Mauritius with tales of wild nights dancing on beaches flings with lifeguards (a cliche, but always fun), and invitations to travel to places like Rio de Janeiro from holiday flames. While I never took up, I was happy to leave these experiences on the plane and go back to my normal life, retreat into myself and not feel thin or pretty enough to talk to guys or be out-going.

My 20’s and early 30’s were spent in one long-term relationship, a few shorter ones, and several flings with extremely inappropriate men who did not always treat me in the way that they should. I was focused on my career in the non-profit world. I didn’t always have time for anything else, and holidays were solely a time to rest and recover from a demanding schedule. 

But then suddenly in 2017, I became the holiday romance myself.  I met an Italian American man in a pub in London whilst he was on holiday visiting family following a business trip.

This time, I was the local and he was the one who would soon be leaving. We had a crazy night with a lot of alcohol involved. The next day he took me for gelato, and then I never thought I’d see him again. The fact he had an ‘expiration date’ set me loose. I felt like I did all those years ago when traveling and I was my best, most free self.

He left to go home and became another story, one that I’d bring up with my friends, talking about the chemistry we’d had and how hot he was. And we’d sigh, and make jokes about when the hell is Elon Musk going to invent a teleportation device already??!!!

Two months later, a WhatsApp message arrived. ‘Good morning from Berlin’. I was sitting at my desk in my London office and my whole body went very hot as if I’d been set on fire.

It was from him.

He texted that he was a few hours away in Germany on another business trip. I immediately thought to myself, GO. I messaged back ‘Well that’s not very far away,’ and he responded straight away; ‘Then come over here.’

We’d had hardly any contact since he left London and I was EXCITED. I told my boss I’d be going to Germany for a date and she laughed and said sure, why not.

I booked myself a ticket and flew to Berlin the next day.

It was a heady time. I have traveled extensively in Europe but had actually only been for lunch in Germany before when I was quite young so this was a new travel experience for me. He drew me a funny map of the metro system and where I needed to get the train to and promised to meet me at the station.

He had booked a traditional and romantic German restaurant for dinner and it was a really warm evening for early September. We sat outside and drank wine and ate Schnitzel and I remember basking in how good it felt.

Later we met his colleagues for drinks in a very cool outdoor bar and then went back to his hotel. 
The next morning I woke up feeling sad and not wanting this experience to end. But I knew I had to fly home to the UK, and him to San Francisco.

At the airport, I focused on trying to distance myself emotionally from him. I was so scared of getting hurt although being honest with myself now, I was crazy about him. I composed a text message in the departure lounge saying how wonderful it had been to see him again, and how I hoped that perhaps our paths may cross in the future blah blah blah. But essentially, I deliberately drew a line under it. I convinced myself he just saw me as a fling, an ‘expiration date’ and I cut it off communication.

I got back to the UK and whilst we had the odd message, I got on with my life. The telltale signs were there, like when he messaged me on my birthday and my whole soul lit up. But I ignored them, telling myself I just didn’t want a long-distance relationship when really the real reason was that I simply didn’t believe he liked me as much as I liked him. 

I didn’t let onto anyone how much I secretly thought about him. I told myself that eventually, it would go away. I closed the book and kept to myself all the daydreams I had of watching sunrises together on the Golden Gate Bridge, all the songs I would listen to that reminded me of him. I have an incredibly active imagination but I worked hard to shut it down, and repeated to myself that time would work wonders and these thoughts would ebb away. That I’d meet someone else, a nice English chap. 

18 months went by. We had one conversation in the summer of 2018 where we talked for hours, then nothing again.

We dated other people, and I was in a new relationship with a nice English chap when in January 2019 I got a message one morning as I got ready for work (it was 8 hours behind and bedtime in California).

I remember being jolted as I read his name on my phone screen, and inwardly asked myself ‘what’s this about. We had a conversation over text as I had breakfast and I explained I was with someone but would love to chat and catch up. 

Over the next few weeks, I would hear from him every few days. I deliberately didn’t instigate any conversations with him. I was cautious and respectful of the guy I was dating, unsure of what could possibly come of this.

One Sunday afternoon Luciano called me, and we spent 2.5 hours on the phone just talking. It had been years since either of us had done that with anyone and when we hung up he messaged me to say so. I was unnerved but still 100% determined to remain emotionally unattached. 

Yet he persisted. Every few days we would chat over messages and we even had one chat about his recent ex as well as the guy I was dating, and I told myself we had transitioned to friends. But really what was happening was that we were getting to know each other more deeply, growing closer and closer.

In late February, my lovely nana passed away. She hadn’t been well and I was expecting it but it was still a deeply sad time. Losing such a strong female presence in my life also caused me to re-evaluate everything. I started to think more about the relationship I was in, how it made me feel and what I wanted moving forwards.

We had a romantic city break in Luxembourg booked for early March which started out wonderfully but on the final morning, I suddenly had a meltdown over breakfast, realized it wasn’t the right relationship for me, and ended things. I would NOT recommend that to anyone, I was simply devastated by the loss of my Grandmother coupled with the guilt of ending a relationship whilst simultaneously stuck with that person in a foreign country…the poor guy ended up comforting ME rather than the other way around. He was a very good person, just not the one for me.

 I returned to London intent on focusing on my relationship with myself and making that the focus in my life. 

But of course, Luciano found out I was now single and was not very subtle about how pleased he was. Our chats continued and now he started making more direct comments about how I should come out to San Francisco and see him. I continued to laugh it off but gradually over the next few weeks, I started thinking, why not? What was stopping me? I pondered when I could take time off work and tentatively looked at flights. I told myself (and others) this would just one me visiting a friend and having a break but with the amount of chemistry we had, I don’t know who I was kidding.

Eventually, on Easter weekend in April, I booked a flight for the end of May. I splashed out on a premium economy flight with Virgin, keen to make this trip more about the experience than about Luciano so if it all went tits up, I’d still have a nice time.

 Our chats were daily by this point and we started planning things to do whilst I was in California. He told me that he had booked a mini-break to a little village called Mendocino and that I’d be meeting his parents which was the point I really started taking it all seriously. Could this be it? I felt so alive. I counted down the days. What should I bring?!

Packing for this trip felt like such a huge deal, even though I am a regular traveler, I had no idea what to put in my suitcase. I splurged on a load of fancy new underwear one lunchtime which I then hid from my colleagues in the office when I came back to work. 

Finally, the 29th of May came. I was beside myself with excitement and just couldn’t wait to get to San Francisco.

Booking a premium economy ticket was the best decision as it felt so special – I was handed a glass of bubbly before I’d even sat in my plane seat (epic move Virgin) and spent the flight watching movies and trying to relax.

When I arrived at SFO the queues at border patrol were enormous and it was unbearable. It took me 2 hours to get through and my nerves were completely frazzled. The CBP officer made a joke and I stared at him blankly before bursting into crazed laughter, I am amazed they let me in. But they did, and minutes later I was walking out the door into the California sunshine searching for a dark blue BMW.

He got out of the car, drew me into his arms, and kissed me. And it felt like I had come home. The next week was the best of my life.

It was so surreal, this was a man I had not seen in nearly 2 years but getting into his car and driving through San Francisco felt completely natural. We went back to his apartment and ‘re-acquainted ourselves’ before going out for pizza. I hadn’t slept in hours and hours but was wired and so awake. 

The following morning we drove up to Mendocino which is about 3 hours up the coast through redwood forests and vineyards. We went for walks along the beach, ate romantic dinners in Cliffside restaurants, and lay in bed listening to music and drinking wine. I remember he told me on our second night there that he was falling in love and my heart sang because I felt exactly the same way. 

Our arrival back in the city afterward was somewhat disrupted when we stopped for lunch en route and I got food poisoning. I was horrified that with such a limited time together I was suddenly glued to the toilet and throwing up but in a strange way it brought us closer together as seeing how he took care of me just made my feelings even stronger. Thankfully it only lasted 24 hours!

Time went by alarmingly fast and towards the end of the week we began having some serious conversations about ‘what happens next?’. The all-important question was whether or not one of us would ever be willing to move countries. It’s a make-or-break issue for a long-distance couple because if neither of you can ever imagine living anywhere else…you fall at the first hurdle. Thankfully I have always known I’d be happy living in certain other places in the world and California has been one of them since I first visited aged 12. So we knew we had a chance. 

I got back to the UK in a total spin and started learning all about US immigration and what pathways would be open to me. I was reevaluating everything. My career, my home life, my future. I decided to start writing and blogging and build a personal brand in order to create my own job to take to the USA. We had several subsequent trips back and forth across the pond, he met all of my family and friend and I met more of his. I planned to quit my job and have an extended trip over to see him in July 2020 to spend a proper chunk of time together and test my new life in the USA. I spoke to an immigration lawyer, I made plans to apply for a visa.

Then, we all know what happened. Covid.

Suddenly we were trapped apart from one another with no idea when we’d be together again. I had already found tenants for my apartment and booked flights for July and told my boss I was leaving my job…and for a long time, I told myself it would all be fine, that I’d still make it, that the pandemic couldn’t possibly last that long. We all know what happened there too. 

July came and I had to cancel my flight and move in with my parents. My job let me stay on but I was devastated. My mental health was in tatters and there didn’t seem to be much hope of an endpoint. As the months went by and we drew into Autumn I decided to take action and forge on with my original plan and make my own way to the USA whilst it was still legal to travel. I flew to Istanbul which is outside of the Schengen area and therefore exempt from the US travel ban. I spent the requisite 2 weeks working remotely from an Air Bnb next to the Bosporus and then left my job, holding a solo leaving do-over Zoom with a mini bottle of prosecco. 

I finally made it to San Francisco on 1 November 2020. Walking through the airport doors was the most emotional experience of my life and I ran into Luciano’s arms sobbing. I had made it. We were under lockdown but we were together. We had the luxury of 3 months together and never spent more than 3 hours apart the entire time. If that doesn’t show you a relationship, will work nothing will! 

Cut to January 2021 and it was time for me to leave as my 90-day ESTA was running out. But the UK was in a bad way. It was freezing cold and covid rates were sky-high, everyone was under strict lockdown. I was still having to live with my parents and was terrified of catching something on the plane home and infecting them.

Full of anxiety, I felt I had no other options. Then a friend told me about a Digital Nomad program in Belize where he lived at a resort called Umaya Village. Instead of going to the UK, I could go to Belize and work remotely for a couple of months until things got better back home. It seemed like dream come true and I jumped at the chance. Leaving Luciano was so sad but less so than usual as I wouldn’t be so far away and I could come back again afterward. 

And so, this is where you find me, a beach in the Caribbean in Central America. Coming here has been the greatest gift and the second-best decision I ever made after booking that ticket to San Francisco in 2019. I have never felt so creatively inspired and cannot overestimate how rewarding it has been to spend 2 months here amongst the ‘Umayans’, the other digital nomads living and working here. Next week I return to the USA for a short stint seeing Luciano again which is another gift, and then in April, I go back to England. My parents are vaccinated, things are opening up again, and it’s time. 

I will start a visa application later this year and feel more positive than ever about our future. I hope that towards the end of 2021 I can make the ‘proper’ move to the USA along with my cat Ginger Rogers and finally we will be able to move forward from this awful pandemic. I’m so thankful that I chose to have a drink in that particular pub in 2017 and even more so that I said yes to that trip over to California in 2019.

I would urge anyone in a similar situation to do the same, just say yes! It might not work out, but as long as you take care of yourself it can only ever be a positive experience that at worst teaches you something and at best delivers you the love of your life.

Just say yes! 

Rosanna Stevens is a British food and travel blogger and writer who became ensconced in a long-distance relationship after a chance encounter in a pub and never looked back! Now writing for UK and US publications about travel and documenting her adventures in the kitchen and beyond via her blog, Instagram, and YouTube channels. Also, check out her range of recipe ebooks and food styling, and photography guide. 
http://www.rosannaetc.comhttps://www.youtube.com/channel/UCCeJ43eB-RftaIVQOpIYKQghttp://www.instagram.com/rosannaetc

What about you; have you ever had a holiday fling that turned into love? Have you ever met someone while traveling? Please leave us a comment below and tell us about your experience!