Traveling Perks of a Rich Boyfriend

I had travelled with my ex-boyfriend and I was sick of it. We had gotten $49 round-trip tickets to Portland, Oregon and stayed in his sister’s flat. We had gotten cheap tickets to Coachella from Craigslist and crashed in the laundry room of someone’s country club rental on a bed fashioned out of patio furniture cushions. We scored free tickets to Electric Daisy Carnival in Las Vegas and had to stay in a different hotel every night due to availability (as we’d gotten the comped tickets last minute) and budget. One of the hotels was $39 a night. We were slumming it. I loved the guy, but we weren’t truly compatible and the lousy travel conditions (combined with coming down from the disco biscuits and jazz cabbage we would inhale at festivals) didn’t help our relationship at all.

We broke up, and I took it pretty hard. It took me about a year, but I met someone new. Two new people, in fact, whom I dated simultaneously for awhile. For a long time up until that point, I had been the breadwinner in my romantic endeavours and I was ready to let someone else take over and relax a bit.

I’d met Anson on Tinder, and we had met for a lunch date, during which we clicked and he immediately invited me to come to Las Vegas with him. Older, well-dressed, public net worth, etc. He offered to fly my dog, which was the first thing that began to set this trip apart from others. The second was that he worked all day, from before I awoke in the mornings until the late evening. We didn’t do anything together. I was alone by myself for most of the day, and I didn’t particularly mind. There was pocket money on the table when I woke up. I would walk my dog on the strip for a bit, and then explore Las Vegas. At night, we would order room service (for my dog, as well) and talk about the day a bit. It was fairly uneventful, aside from staying in a very posh penthouse suite and riding the rollercoaster at New York, New York. (The views are amazing up there in the day time.) This was the only trip we took together. However, my view of travel had been changed for good. I liked having everything paid for, and feeling indulgent when I was away.

Sven and and I met at a whiskey bar when I was on a date with a man I’d met on OK Cupid. He managed to coerce me away from two men that evening, before stealing me away to a quieter bar to have a drink and a chat. A month later, we were driving to Vegas for a brief holiday.

It was a very different experience than my last time in Vegas and the whole purpose of the trip was for us to be together, somewhere other than Los Angeles. Very different than tagging along for a work oriented trip. We dressed to the nines, me in my Nicole Miller little black dress and a pair of Marc Jacobs high heels. He was a former model and had appeared in Vogue, so although he was older, he was very handsome and distinguished. We dined in a restaurant overlooking the Bellagio fountains, where I had the best gnocchi to date. We gambled, smoked Dunhill cigarettes, chatted over caviar and champagne at Petrossian, and drank copious amounts. We were having a great time, and we quickly planned another vacation together.

Next up was New York City. After a heavy night of clubbing, drinking, and drugging with my friends, I missed our flight and the million phone calls he had attempted. I ended up flying into New Jersey and making it to the hotel at the same time that he did. He took the whole thing surprisingly well. We made it to our reservation at Momofuku Ko. Things began to get a bit embarrassing for me at this point, which is something that I feared would happen all along.

One of the things that certainly comes with age, for most people, is wanting things to be a certain way. Especially if you’re a rich, white guy. I had seen his moodiness appear briefly when we had checked into the hotel in Vegas, he wasn’t entirely satisfied. I could see the tell-tale signs of an on-coming temper tantrum, much like with a two-year-old. At the time, I talked him down and we proceeded to have a nice evening. I had seen this pop up occasionally in Los Angeles, as well. Particularly when we had to settle for banquette seating in a restaurant, there wasn’t seating in the part of the restaurant he desired, or when the bar at his country club closed early. At Momofuku Ko, he began refusing food at six courses in, only about half of the menu at this tasting menu-only restaurant. He instead stood outside of the restaurant, smoking, talking feverishly on his mobile, and pacing. I sat inside, talking to the Sous Chef and eating and drinking alone.

Later that night, we went to see a band of his choice at Bowery Ballroom, which was unremarkable. I felt decidedly out of place with him amongst all the hipsters and PBR tallboys. No matter what the situation, he was always dressed as though he was just walking off of Wall Street. Relief flooded my body when he suggested leaving. We decided to go to a speakeasy somewhere, which was infinitely more appropriate. In my drunken state, getting out of the taxi, I left his beautiful Brooks Brothers top coat in the taxi. It was never to be seen again. My dog, Pepper, and I were rewarded with a Brooks Brothers shopping spree the next day. Although I had to put up with a bit of arrogance and a finnicky attitude, it certainly paid off in material goods. (And I’m living in a material world so I am a…) Right after New York, he flew Pepper and myself to Washington, D.C. to see my mother. I was loving flying with Pepper. That was the biggest perk so far to travelling with my wealthy, older, boyfriends.

Despite a few hiccups I had felt during our courtship, I agreed to go to Mexico with Sven. This is where it all began to go to hell. He had been waiting months for his new release Mercedes. He got it on the morning of our trip. This somehow contributed to him being terribly late to pick me up. (Which was really fair, considering my last indiscretion.) He became even later when he realised on his way to collect me, he had left his passport at home. We were flying out on the 2nd of January, and the airport was a mess unlike anything I’d ever witnessed. People were queued up out of the doors and across the pedestrian bridges.

Sven was pissed. I had already resigned myself to the fact that we weren’t going to make our flight. On the other hand, he seemed to take it as a challenge and a cue to shout at people who really couldn’t help us. Eventually he calmed down and accepted our fate. Plans were made to stay close to the airport in Santa Monica and we settled in with some drinks and dinner reservations. Sven was still a bit on edge and I had learned now that when he had a bit of a sulk, it could prove difficult to get him out of it at times. Later that night, we dissolved into an argument.

He couldn’t believe that I didn’t want to have sex on my period. We had been seeing each other for months and this was the first time I had refused him. Four in the morning was when we were supposed to get up to catch our flight but we bickered past one. I finally told him that I was going to lie down and go to sleep. He woke up at three in the morning, turning all the lights on and slamming things around. It was then that he informed me that he was leaving without me. I replied that that was fine and that I really had no desire to go to Cancun with someone who was pissing me off so much. I told him to kick rocks. I listened to the wheels of his suitcase squeak all the way down the hall. Then I listened to them roll back, and he burst in the room, full of apologies.

I grudgingly climbed out of bed and readied myself for our trip to the Caribbean. We stiffly sat in the airport, then solemnly sat in silence on the plane ride. He worked on his laptop the entire time until he timidly placed his hand over mine. I tried to forgive at that point in order to embark upon a pleasant experience. Upon arrival at the Ritz-Carlton, we had to change from our original room, as Sven claimed we’d been promised a room on a higher floor with a better view. The poor bellhop lugged all of our baggage back to the first room we were placed in after the second was met with his disapproval.

This was how it went. Everything was seen by him as a chance to negotiate for a better trade. One night, God apparently took mercy upon my sanity; because a lit joint dropped from heaven and onto our balcony to help appease my disgust as he puffed on a cigar.

He worked most of the days, as I sat by the pool, anesthetizing myself with a continuous string of drinks that I charged to the room. Otherwise we ate at posh Argentinian steakhouses, rented jetskis and shopped for silk Pineda Covalin blouses, had couples’ massages, and of course… drank ourselves quite silly. It was a good time, despite his hissyfits along the way. It had certainly solidified my love for traveling in luxury. The last trip had taught me that it was important for me to plan activities for myself if my partner was working; it wasn’t good for me to wait around.

My friend also had her fair share of travels with an older gentleman, Norman,  that she was seeing that had come into some money. Her most amusing story was probably one of when they visited Prague.

They had gone clubbing a few times while there and my friend was definitely feeling a bad case of grandpa-itis. It got to the point where she would excuse herself to the restroom and purposely ditch him for as long as it took him to find her in one of these multi-room megaclubs. This later resulted in him standing obsessively outside of the door of the toilet and not allowing her the chance to disappear. But on this trip, she managed to trick Norman.

Norman her was not a hip, free spirit at all. He was quite literally a craggy, archaic, hermit of a man who was perpetually disgruntled and quite out of touch. To give a bit of background, when I met up with them in Vegas, his drink was Baileys and heavy cream. That is not the drink of a normal person. It is the drink of an alcoholic 11 year old. Even the jaded waitresses of the casinos couldn’t help raising an eyebrow at such an order.

In what i suspect was some attempt at impressing her, Norman told her he suddenly was struck with a craving to score some weed from one of the dodgy characters outside of one of these night clubs. This was totally out of character for him and was made doubly ridiculous by the fact that they were visiting from California – a place rife with some of the best quality cannabis in the world. She was miffed and had no wish to partake in buying drugs from a dealer who was probably preying upon tourists and foreigners.

He insisted upon doing it and she left him to go wait inconspicuously and warmly in a nearby pub. His transaction began taking a long time. Multiple scenarios flowed through her mind: he had gotten beaten up and mugged by some thug, perhaps he was arrested by an undercover cop and was waiting in a jail cell somewhere, or he had gotten high and was wandering the streets of Prague in a haze of stoned confusion. She admitted to me later that she was actually looking forward to having a hotel room to herself and would probably leave any legal woes for his kids to handle, should it come to that.

To her dismay, Norman eventually returned. He had given the dealer fifty american dollars for a gram of weed. The drug peddler had said he would need to run to his car to get change and, of course, never returned. Norman waited in the rain on that street corner for an hour, waiting for his ghost change. That part was predictable but once he produced the marijuana for her inspection and opinion, was when things curved towards the ludicrous.

He had been given a bag that comes with your trousers with the spare buttons inside. There was even a hole in it. Inside, were a few very Charlie Brown Christmas tree looking twigs that had obviously been broken off of an ordinary garden bush. It resembled nothing similar to pot. It had light brown stems and fat, fresh, thick, leaves much like a succulent. It still had raindrops clinging to it. Closer to the bottom of the little plastic sleeve, were crystals that looked like bath salts. It was as though if Norman’s judgment was so impaired that he couldn’t realise that he had NOT purchased weed and he got to the point of smoking it, the dealer had sprinkled some other drug on it to charitably bestow some kind of trip on the guy. C’est la vie.

Dating rich guys can get fun. However, sometimes confidence becomes cockiness. A drive for perfection can end in dissatisfaction. At times there are displays of classism and elitism. If they’re successful, they’ve worked hard to get there and sometimes are a bit uptight. You have to force them to relax. And they desperately need to get out of work mode. You might end up spending a good chunk of time by yourself. Budgetary concerns are a non-issue but a slew of other problems do arise.

Travelling with your wealthy boyfriend definitely beats travelling with your broke-ass boyfriend. These days, I’ve found a new travel companion in a more humble, young entrepreneur whom I adore. Our first trip is nowhere exotic, but he is helping me to reach my goal of visiting all 50 states. (Cincinnati, here we come!) He’s proven himself capable thus far of balancing his work schedule so that I never feel neglected. And when he’s too busy, he just buys me shoes.  Which is just fine with me.

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