The Westin
A Twisted Valentine’s Day Tale
“Please just take it for the cab ride home” — The Westin
Early on in Portland, I am part of a downtown crowd that isn’t really my scene. I met these party people during my post-Israel vacation here. I wind up at clubs and bars with people who have little soul but were fun nonetheless. One Thursday night there is a Facebook pandemic from promoters for a black-out party at the downtown club, Dirty. I go because I don’t yet have a job here, don’t have to wake up early the next day, and I love parties. Why not?
I wear a dress I got in Paris—satin tutu-like bottom up to here, sparkly black plunging neckline down to there—and a white fuzzy hat because it’s January and it makes my big blue eyes pop, which will take some attention off my breasts and legs in this dress, or so I tell myself.
As soon as I walk into the place, a beautiful man at the bar, at least 35, hones in on me like a guided missile, and I want him immediately. He knows the owner, isn’t a big fan of the club, is in Portland on business, and insists on buying me drinks. He can’t keep his eyes off me. He asks me to dance and we do, and then we start kissing. Soon I’ve lost the friends I came with, I’m not crazy about the wannabe strippers around me, or the strobe lights flashing everywhere, and on top of it all, I see the biggest douchbag in downtown Portland (mansion party guy) out of the corner of my eye.
This new man at the bar, the gorgeous stranger of a businessman buys me one Jameson after another and then asks me to leave with him to go to the Spin Room next door. I say no because I don’t know what the Spin Room is, and I’m still thinking I might hook back up with the people I came with. But a couple of hours later and after one too many LMFAO songs, he asks me to go to his room in the downtown Portland Westin, and I say yes.
In the morning, Westin wakes me by kissing me as he’s getting out of our huge, white, plush bed overlooking the city, at least 10 floors high. I’m naked and happy and reminded of our night just looking at the mini-bar bottles and condoms strewn around the room. I hear him getting into the shower, and I sleepily roll out of bed and follow him in. He smiles as he sees me get inside the glass with him, and everything that happens in that beautiful shower is as sexy as you can imagine. Afterward, he dries me off, wraps me in a super-soft oversize robe, tucks me back into bed, and tells me to go to sleep. He calls the front desk and extends the check-out time for me as he dresses in his Brooks Brothers suit and Cole Haan shoes. I am euphoric in that moment.
He kisses me on the lips and forehead and whispers that he’s going to leave me money on the dresser for my cab ride home. I insist he shouldn’t, but after he leaves, I see cash on the bedside table. He also leaves behind his favorite Pringle sweater that he got in Edinborough, and I remember telling him I didn’t want to take a cab in the middle of the afternoon in my sparkly and very small party dress from the night before. Broadway Cab has always seen me at my messiest.
I call my dad. I want to know if I have legit gone from Portland party girl to someone who may have just been paid for sex. My dad says, “Enjoy that cozy bed! The money is for a cab, you don’t have a job there yet. He gets it.” I don’t know if he realizes that my slush fund was 10 times as much as the cab would cost that day. And there was that ridiculous hot and steamy, sexy shower…
This was my first time staying in the Portland Westin, but definitely not the last. Though I didn’t know it at the time, he’d be back soon. The very next weekend he surprises me, calling to say he’s just flown in from Southern California, where he lives, and wants to see me. He says he has a business dinner meeting, and we agree to meet after at my favorite Irish bar downtown.
It is snowing and chilly, and I wait for him at the bar for a long time. I assume he’s probably drinking shots in the Pearl at Blue Hour on his business dinner. I’m okay though. My bartender is around his age, with piercing blue eyes, and he’s eye-fucking the hell out of me as I wait patiently. Westin eventually shows up and slides next to me at the bar, kisses me intensely, and quickly orders us both top-shelf Scotch from the library of liquor. He tells me he loves the live music, and this bar I chose. We talk about where we attended college, our families, our career plans, passions, studying abroad in Europe—him in Scotland, me in Ireland—and we can’t keep our hands off each other. It’s romantically obnoxious.
He then tells me he wasn’t supposed to come here to Portland for this meeting, but he had to see me again immediately. This leads to him promptly paying our bill, and us taking a short cab ride back to the downtown Westin.
That night he opens up to me about his two kids but never gives a straight answer as to whether he’s still married, or for that matter ever was. And this initiates a long discussion of how that is even possible. He says, “I want to make sure you are okay with all this.” I don’t know if I am, or what I am supposed to be okay with. I‘m a little taken aback, perplexed, yet I tell him I am open to explanation, but I might want to go home that night. He understands, throws me some Ketel One nips from the mini bar, and we keep talking. He explains how he never had a wedding, but rather a common-law marriage for his family’s sake, and that everything with his “ex-wife,” who is now more of a “friend,” is over. Their families are connected, and I assume that has something to do with money and his kids. He’s a successful lawyer, regularly in Portland these days, trying to close a deal with a pharmaceutical company here. Fucking lawyers. The mini vodka bottles and his honesty sway me to stay, which leads to some hardcore sex and another heated Portland Westin shower, which in turn leads to another generous cab-ride slush fund in the morning.
We see each other quite a bit that winter, and we seem to really like one another. I wear his sweater on chilly lonely nights in my apartment wondering if his ex-wife ever wore his “favorite sweater,” walking around with nothing else on. Whenever I give him this visual of me in his Pringle sweater lying in bed, naked underneath, it makes for a good starting-off point for phone sex.
About a month later, he proves to like me enough to fly me down to San Francisco on Valentine’s Day while he’s on business there. He’d booked me a flight the night before while we are talking on the phone, and a little sleep-deprived I cab it to PDX and am off. When I arrive at the San Francisco Westin, he’s in a meeting and the concierge says our room isn’t ready yet because my partner upgraded to the penthouse. I only have a purse stuffed with a party dress and lingerie so I happily go out to explore the city.
Around 4 p.m., we meet in the room, I had just gotten out of the shower, and he walks in, and we have one of those moments. The kiss is unreal, we are naked within seconds, and I want him so badly as I push him onto the bed and climb on top of him. We laugh, and then agree to wait until later to fuck. He is so happy to see me, says we have this connection, and is overjoyed that I came here on a whim to visit him. We agree to meet at 10:30 that night after his business dinner. He leaves me some cash to have fun with until he can take me out later.
And as I spend Valentine’s evening in an expensive hotel bar, waiting for him for hours a friendly stranger buys me drinks. I tell him why I’m here. This very good-looking gentleman says, “I had a ‘you’ once, a ‘Jess,’ but I ended up back with the mother of my children… just so you won’t be surprised if that happens. But seriously, you’re gorgeous and smart and can handle whiskey. Give this guy hell when he comes back tonight.”
We drink together as we watch the CNN footage of Whitney Houston’s death, which had apparently happened earlier that week. Dr. Drew comes on the bar’s flat screens and my new friend tells me he went to school with him at Amherst College (five miles from where I grew up), and shows me his number on his cell. After a few Jamesons, I’m convinced we should call him. I am so tempted to leave a voice mail for Dr. Drew Pinsky, seeking advice about my man issues that night, from the Ducca bar in the San Francisco Westin. I even convinced myself I’d be at the top of his priority list.
My friend Westin won’t be showing up any time soon, but he keeps texting me. Last call comes and goes, and the bar closes. I take the elevator with my new friend who just paid our entire night’s bill and is probably wondering why he’s staying on a lower floor while I’m going up to the 32nd; or why he isn’t the one getting the opportunity to be with me tonight. As we hug goodbye, he says to me again, “Seriously, you’re amazing. Give this guy hell. Maybe lunch tomorrow?” I’m considering it.
Westin comes in shortly after, we get into bed, and he tells me how he stayed out until 2 a.m. with business partners taking tequila shots and how it’s all part of the job. I get it, but I flew to San Francisco for him on a few hours notice when he invited me for Valentine’s Day (not that I care too much about the holiday; I just think of it as a precursor to St. Patrick’s Day), but the whole thing is a little disconcerting.
Around 5 a.m. we’re both talked out on everything from that night to how we feel about each other, his situation back home, how I think I never want to get married, me never wanting kids, his kids, how his ex-wife/friend doesn’t know about me, their non-existent sex life, our very existent sex life, Portland, San Fran, this trip, us. He sweetly asks if he can help me get out of my gold sparkly party dress, and then he gets on top of me, and we fuck. The way he handles me is gentle and rough all at the same time, and it’s good. And then we both pass out.
The next morning he’s off to more business meetings, and I awake to another slush fund, a beautiful view of San Francisco, and positive thoughts about the rest of the trip. Alone and happy, I gallivant throughout the city. I take a boat tour around Alcatraz and under the Golden Gate Bridge, relax in a sushi/sake lounge for lunch, partake in some shopping, chill on a park bench, get drinks at Fog Harbor on Pier 39 overlooking the water, and walk until I almost drop. Finally, when my six- inch stilettos can’t take it anymore, I hail a Pedi cab for the ride back to the Westin, stopping at Cask first so I can buy some Whiskey for the room. I love a breezy, sunny city in February.
I come back for a breather and shower because I think Westin might have a break and time to play before another dinner meeting that evening. Wearing only my fluffy towel, I am on the bed, hair wet, sipping whiskey, watching MSNBC, and he comes in and is quite sick, sweating, not looking good at all. He immediately goes into the bathroom and starts throwing up, and says he thinks he needs to fly home to Southern California.
I don’t know what to say. I ask if it’s me, wondering if all my questions the night before were too much, and he assures me otherwise. I have an overwhelming yet unnecessary feeling of Jewish guilt. He tells me how sweet he thinks I am, and how beautiful I am, and how he doesn’t know anyone else who would fly to a random city they’d never been to on a whim and just explore for days on end, alone, waiting for him. He keeps saying he doesn’t want to be sick in front of me, and when say I want to take care of him, he doesn’t want that either. I give him the trolley-car souvenir I bought for him at Fisherman’s Wharf, and we say a gloomy, confused goodbye. I am pretty sure this man will never see me naked or in a party dress again. He tells me he paid for one more night at the room for me, and insists that I stay to enjoy it.
I take the little bottle of Jameson I got at the store and the almonds I bought, which are now dinner, into this luxurious bed and call my best friend in Portland, my Special Friend, feeling like the loneliest person on earth in this most ridiculously beautiful place.
My meltdown phone call is prefaced with, “Please don’t hate me; this is the biggest first-world problem ever.” He says he loves me, and then tells me to walk over to my floor-to-ceiling window and take in the San Francisco skyline, all lit up at night. It looks magical, and for another night on Westin’s dime, I stay here, talking to the Special Friend with a slush fund on my dresser, which I’ll use to get home, and then some.
The next day, I take the Westin town car to SFO for my last luxury indulgence. I have a sexy Sayid-like Iraqi driver, who used to be a translator for the U.S. military. He doesn’t even charge me because he’s so amused by my entertaining stories of the last few days. And that’s really the beginning of the end of this whole twisted fairy tale. I can’t get a flight to save my life since I am flying stand-by, so I spend 12 hours in the godforsaken SFO airport.
I do meet a 6’8” gentleman a few years older than me at the first bar. He is on business, away from his beautiful pregnant wife. He shows me pictures of her and is so genuinely happy to be in love and expecting a child. He gives lectures across the country to college students on the dangers of drinking. His company is hugely successful, making these anti-drinking campaigns and promoting them. He later pays for our several double Jamesons, saying he can expense them. Huh?
I also meet an awesome, rock-star lesbian who is in San Francisco for a rally against a church lawsuit on gay rights. Her partner is the head of a church back in their hometown in North Carolinia. She tells me they have two daughters, two hybrid cars, two cats, and she buys me tequila shots. Her toast goes something like, “Fuck them, if they say we can’t live our life!” Rock on! But there is only so much you can drink in airport bars, and only so many decent people to talk to in them. After a while, they all have scheduled flights to catch.
The airport starts to get rough. There are only so many newspapers to buy and read in one day. There are also the very unhappy workers who feel they can be bitchy to me since I’m flying standby. And then there are only a few bars I didn’t find during the first eight hours, and they don’t serve Jameson, only Bushmills. I have to draw the line somewhere.
I make a few frantic phone calls to my parentals and some friends in Massachusetts. They seem so far away. And then I just wait for my plane. These first few months, living on the West Coast on my own, have been full of surprises, and nothing has been easy. I am returning to the dreaded Kearney Curse apartment that I’m desperately trying to get out of, with the most disrespectful human beings I have ever known co-habitating with me. On the horizon are some job interviews, but nothing particularly promising career-wise. I’m on my way back to a place where a lot of people have already let me down in terms of character, trust, and friendship. It’s almost tempting to seriously consider a flight back to the East Coast, but I don’t.
I suck up the tears, think about the truly great friends I have made, the adventures I have already embarked on, the hilarity of the whole situation, and I breathe. The televisions showing Woody Allen and Dick Van Dyke help as I pass from one airport terminal to another, as do the Bob Dylan and Tom Waits tunes in my iPod… and then I finally catch the last flight of the day back to PDX at 12:50 a.m.
Westin texts to make sure I’m okay—in the airport, and later when I get home around 3 a.m. (after I’m pretty sure a Russian cabbie ripped me off and wanted to whack me when I confronted him on his overcharging me for the late-night fare). I text back that I am okay, though just barely. After entering my apartment, I see the despicable housemate couple and their poor dog that’s left disgusting messes everywhere, including my bathroom. Indisputably, I’ve just gone from a luxurious penthouse to a squalid doghouse. Westin texts back, and he is starting to feel better. Thanks San Fran… It was real.
I honestly don’t remember if Westin and I had one more encounter back in Portland after that tryst. We texted a few times, but his business deal here evenutally fell through, so after a few months he doesn’t come back. I am grateful for the times we had, and for those slush funds while I was still unemployed those first couple months. I really did like him, but maybe the Ducca bar friend was right, and he went back to the mother of his children. It doesn’t really matter.
Strangely enough, eight months later, I’m lying in my own modest bed, naked, with a new man, trying to catch my breath and sweating. It’s August, it’s hot, and the sun is pouring onto us through my bedroom window. The sex is insane, and I want it again so I start kissing his chest and up to his neck. He makes this sexy growly noise and smiles, and he’s definitely ready again. This man is an animal. As I crawl on top of him and look into his piercing blue eyes, something clicks. It occurs to me that I’d seen him before meeting him just a month earlier. I flash back to one of my early nights with Westin, suddenly realizing this man—ready to have his way with me again in bed—is the very same bartender from the Irish pub, the one who was eye-fucking me to pieces as I waited for Westin. He is the one who poured our top-shelf Scotch that chilly January evening. He soon will be known as The Mister.
