I’ve Matchmade 9 Happy Marriages (Including My Own) Here’s the Surprising Secret to My Success

If Bangkok were a lady, she’d be doused in an intoxicating, smoky perfume. She’d exude confidence and buzz with mystique. And three years ago, when I serendipitously met my Danish husband, Jonathan, on the notoriously devilish Khao San Road in Thailand’s capital over a Chang beer, little did I know Lady Bangkok had pulled up a plastic stool beside us, smirking.

I was a millennial cliché, haphazardly exploring Southeast Asia while working remotely as a freelance writer and matchmaker.

That’s right: perpetually single and unable to score a second date in Manhattan, I somehow had a knack for impersonating the Yenta from Fiddler on the Roof, matchmaking clients nationwide. And though I’ve been applauded for my “people skills” since the days of parent-teacher conferences, it wasn’t this trait that made me successful as a matchmaker.

While many believe matchmaking requires a keen understanding of romance, it equally necessitates understanding physical location. Grasping how location and romance intersect is paramount for every relationship stage, from the first date to the eightieth wedding anniversary.

I’ll divulge some matchmaking secrets below, many of which I’ve experienced firsthand. After all, meeting my Prince Charming in Thailand, I knew it was finally my turn. And I swear Lady Bangkok gave me an encouraging wink before fluttering into the chaos of the metropolis.

Olivia and Johnathan Liveng in Phuket, 2018Olivia Liveng

Choose a First Date Location Where You’re Comfortable

If I knew I was about to meet my husband that fabled night, I’d have changed out of my staple Chiang Mai elephant pants or run a brush through that persistent dreadlock. But, to be honest, this look—barefaced, slightly burnt, and minimal effort—is my physical and psychological comfort zone. Between the ill-fitting heels, the begrudging makeup slathering, the stilted conversations about Brad’s (isn’t that every NYC finance boy’s name?) and the tedious work hours, I always felt like an imposter dating in Manhattan. Yet my only choices were conforming or succumbing to a perpetually single existence. Or so I thought.

There was no concealer or mascara to hide behind that night I met Jonathan. Instead, I was wearing an outfit I’d typically change into once said-Brad date ended. Jonathan embraced my core identity (quirky, somewhat unstylish) from the get-go. And that’s precisely why I emphasize to matchmaking clients that choosing a date location where you feel secure is necessary. Clumsy and awkward in heels and skirts? Skip the cocktail bar and opt for a bowling alley or park instead. Get shivers recollecting 9th-grade English read-alouds? Maybe avoid a live-poetry jam session.

Choosing a date location where you feel secure is necessary.

Additionally, this hyper-spontaneous setting, which forced Jonathan and me to decide within hours to cancel our separate plans and travel together, allowed our love to spiral so naturally and openly—we ended up spending a blissful month meandering Thailand together. Whether it be Bangkok or Central Park, deciding a first date’s location is critical. Regardless of chemistry, conversation, or even outfit choice, an uncomfortable date location is a pathway to disaster.

I’ll happily divulge a few of my first-date location secrets for those without a personal matchmaker to curate dates. If you’re prone to nerves, it helps to have previously ventured to said location to minimize curveballs. Were you always more comfortable sharing secrets at slumber parties once the lights dimmed? Choose a bar with a demure ambiance. If you’re meeting at a restaurant, make sure there’s a reservation already made to avoid awkward mingling.

Besides the location, the first date activity is also critical: I always design first dates for clients that align with their personality and adventure styles. For example, I would never send a more subdued couple on a scavenger hunt around New York City, but have set up adventurous dates exploring Hamilton Heights for more intrepid spirits.

Occasionally Escape Reality…Literally

Little can metaphorically cock block romance quite like reality. Jonathan and I got serious at turbo speed—moving to Denmark, meeting extended family, even attempting to bake kanelsnegle (Danish cinnamon bread) within days of our Thailand escapades. This next stage of a relationship inevitably involves prioritizing discussions around bills, logistics, and other valuable conversations.

While a relationship’s progression is natural, it’s refreshing to occasionally mute reality and relish in “us time.” The remedy? Exactly what I’d tell clients: Turn off phones throughout date night and stop scrolling Instagram while watching television together. Phones are especially taboo on a date—just think: how refreshing it is to meet someone not tethered to their device! And, of course, plan romantic getaways!

A staycation near home requires minimal effort and temporarily transports from reality. There is just something about freshly pressed linens and room service that reignites flames. Knee-high in wedding planning (and laundry piles) last summer, Jonathan suggested we book a night at the newly opened Villa Copenhagen, a seven-minute bike ride from our apartment. Though we could see our local supermarket from the hotel’s rooftop pool, we felt reinvigorated. Similarly, once when in a rut, we treated ourselves to a luxurious stay at Copenhagen’s most timeless property, Hotel D’Angleterre, where a romantic couples massage and detox bath ritual quite literally rejuvenated us. I could finally understand why my parents joke that I was “created” on a staycation in neighboring Massachusetts 28 years back.

Even when traveling, don’t be afraid to kick back in fluffy hotel robes with your lover, diminishing the need for constant external stimulation—after all, sometimes chill time is the most restorative activity for a relationship. For example, Jonathan and I recently visited Manhattan and, instead of matching the pace of the City That Never Sleeps, we took advantage of our own sleep cravings, drawing warm bubble baths in our bathtub of the Financial District’s Gild Hall Hotel and uh…snuggling…in bed 46 floors above NYC at The Arlo NoMad, blissfully ignorant to the commotion outside the glass windows of our corner room. The ability to slow down and turn FOMO into LOMO (love of missing out) with your sweetheart is the ultimate escape.

Travel Alone…Seriously!

It’s indeed possible to become too comfortable in your relationship comfort zone. While Netflix n’ Chill nights are occasionally necessary, resentment may brood if you’re too intertwined. It’s akin to a stale career: you need new challenges to stay focused and succeed. And one of the most productive ways to disrupt the mundane is traveling…alone!

Clients often are puzzled when, only months into their relationship, I advise they go on a solo getaway. But the ability to prioritize a partner while remaining independent is a desirable human trait and adds intrigue to the relationship. For instance, I decided to circumnavigate Mont Blanc with Boundless Journeys just six months into dating Jonathan— five strangers joined me, but not him. When I returned home with defined calf muscles, anecdotes referencing mountain goats, and a newfound appreciation of fondue, I swore Jonathan thought I was Maria von Trapp. And he found that quite sexy.

Maintaining your own separate set of friends to occasionally galivant with is also critical. (Don’t let friendships slip just because you’re taken!) Worried her marriage was going stale, I once convinced a client to book a revenge girls’ trip to Iceland. Surrounded by gal pals, omnipotent nature, and a few days’ necessary distance from her hubby, she returned home more rejuvenated and enamored than ever. And her husband found that quite sexy too.

Olivia and Jonathan in Petra, 2019Olivia Liveng

The Secret to Prolonging the Honeymoon Stage? Annual Honeymoons!

The honeymoon period of a relationship conjures up a sense of pure euphoria. But what’s stopping you from replicating that cherished time repeatedly? The solution—annual honeymoons! They are a time to get away from everything and nurture romance. I also suggest clients craft annual honeymoon itineraries together, which heightens anticipation (and no wedding stress this time!). Consider rewriting your vows for said honeymoon as well, to remind one another (and yourself) of your divine bond.

Just like selecting a first-date location, choosing an amorous annual honeymoon spot is paramount. The Maldives, often regarded as the world’s most popular honeymoon destination, is also optimal for honeymoon numbers three, four, or even fifteen. Adults-only resorts such as Hurawalhi relieve from distractions of screaming children, re-centering focus on your relationship while soaking in sunshine and devouring seven-course tasting menus at 5.8, the world’s largest all-glass underwater restaurant.

However, the reality is once life gets more complicated, you’ll often need to bring the kiddos along. That doesn’t mean that romantic honeymoons are obsolete. Even in the Maldives, resorts such as Kuramathi and Cinnamon Hakuraa Huraa have dedicated children’s clubs, so you can clink champagne glasses in your overwater villa’s plunge pool while the kiddos are separately entertained.

Lady Bangkok Returns

Olivia and Jonathan Liveng, Nashville 2020

Our most recent adventure was to Nashville, known for its rowdy bachelor-party scene and greasy chicken. But Jonathan and I weren’t looking for lavish—we wanted to dance, drink cheap beer, and flirt with one another. Broadway, Nashville’s equivalent to Khao San Road, tasted humid that first evening we arrived. My makeup had sweat off, and I opted to wear a loose-fitting printed skirt in anticipation of all the fried chicken and mac n’ cheese we’d consume. The hillbilly twang of the live band reeled us into Robert’s Western World, one of Nashville’s most beloved honkey-tonks.

Jonathan disappeared into the crowd as I got lost in the melodic tones of James Brown. When he returned, he smirked and handed me a Pabst Blue Ribbon. “It’s no Chang Beer, but it’s the best I could do.” As I took a sip with my unmanicured hand, which now has fossilized our commitment in diamond form, I could have sworn, ever so briefly, Lady Bangkok gave me another little wink.

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