The Portland Socialite

Guest Post from Gerard: Sext Poetic

There is no medium that can’t be improved upon by the socialite. Sexting is basically slumming it on your smartphone, but in the right hands the gross and hilarious becomes the risque and scintillating. Don’t get me wrong, I have never not laughed uncontrollably during a sexting session because come on, just think about the positions we contort ourselves into for the composition of a drool-worthy sext. 

If you’re still reading, either you know what I’m talking about or you’re fooling yourself into thinking you’re just humoring me. But you and I both know you want the socialite tricks of the sexting trade. Leave your shame at the door, as there’s no room for excessive dignity in this game (i.e. Don’t be a killjoy and have some 21st-century fun - everyone is doing it). 

Now, anyone can fire off a dick pic and/or tit pic (guys have tits too, and let’s not neglect those outside the binary). But unless you want to “Anthony Weiner” your life, a bit of tact is required. A good rapport is essential with a potential sextmate (who, by the way, is not necessarily a one-time partner). By that I mean you’ve talked in person at least once and have made the requisite physical evaluations to know that this is worth it. Hopefully you’re rational enough to determine that your sextmate is respectful and stable enough to be responsible with your… likeness. Keep in mind that these are going to be in the ether. So heed the following:

-Don’t include any definite ties to your identity (incriminating tattoos, unique bedspreads, NO facial features, obviously)

-Keep in mind the potential for a “leak:” be sure that you’re only sending very, very good sexts. I won’t say that all publicity is good publicity, but hey, you might as well put your best self out there. 

-Take more than one picture at a time with subtle variations in between. Your first shot will rarely be your best.

-A good socialite always plans ahead. The next time you’re feeling particularly attractive, snap a few choice pics of yourself to have on hand. The opportunities to sext can come when you can’t sneak away and pull down your pants. And sexting in public while your friends are unaware is a lovely treat. 

-Keep the sexts you receive and create a locked folder on your phone. For your records and for insurance. 

-As far as composition goes: low light is your friend. Strong, overhead light is not your friend. I FORBID you from sending mirror selfies. Not classy, not ever. Instead, just find parts of your body that are particularly photogenic (a mirror might be necessary for this stage) and snap away. This will vary from person to person, but generally backs, butts, and the chest region are going to be safe bets and identity-securing. Those of you with dicks: the straight down, point-of-view shot is pretty boring. Try a shot from in front of you while sitting or reclining (Gerard pro-tip: If you have abs, this works particularly well). In general, getting your legs/thighs involved in the image is a good idea - this might be in the form of framing the *ahem* main attraction or making your pic just a bit more mysterious by partially blocking certain *areas.* 

-Finally, talk with your sextmate and see what they’re into. Firing off sexts at will is an amateur mistake. The quid pro quo approach is usually a solid one, and try to make a game of it. The “send me pics of what you’d like to see of me” is a fun method. Having a bank of images to pull from is very helpful in getting the ball rolling, and from there it’s easy. Be sure to be vocal about what you want, coy or demanding as the situation requires, and you’ll have a great time. 

Who Else Thinks Lily is Up To Something Sketchy?

  • Facebook chat with Lily. Portland, Oregon sometime between 4-5 PM
  • Lily: Can you Snapchat texts? Like send a text that you'd want to have disappear?
  • Danielle: Well Kind of.
  • You can caption pictures
  • I don't know if there's an app where you can just send disappearing text
  • Why what do you want to do?
  • Lily: Well cuz sometimes I wanna send a text
  • but i don't want there to be a record of it
  • like sometimes you want to say something but you don't want it saved. Because people show other people texts, duh.
  • Danielle: You can still screenshot snapchats
  • Also then why don't you just call them?
  • Lily: I know but you know if they've screenshotted them and I'd only do that with someone too dumb to know how to screenshot!
  • And sometimes you don't want to talk to someone, but just want to communicate a textual thought
  • Danielle: I'm really perplexed about what you'd want to say to someone that you wouldn't want saved.
  • Can you give me an example?
  • Lily: Just stuff you don't want to have as evidence like DUH.
  • Danielle: Um. Okay. I'm going on a walk. See you at Andina and bring my juicer with you pls.
  • Lily: K bye laterzz

Glossary of Affiliates Volume 4

It’s been several months since our last post and naturally as Danielle and I are still single there are bound to be a couple of affiliate additions to pin onto the prior lists. Enjoy. 

Prior glossaries below:

Part 1

Part 2

Part 3


  • Bad Sex Ben: Terrible, terrible, atrocious sex. Entirely disrespectful and regrettable and by far the worst sex of my life and far worse than I could have imagined. In a nutshell: Under two minutes of jackhammering and a high five after a BJ. He is a terrible dresser and post coital was spotted in a drug rug. He is a friend of a friend and has now become someone that all the socilates glare menacingly at when we see him in public. Closest thing to a redeemable quality is a neat tattoo on his back.
  • Plane Paul: I traveled first class returning from my mini trip to Fiji because I booked my ticket last minute and there was nothing else available (as if I would have taken anything else). I’ve been throughly engrossed in a popular scifi fantasy series that everyone else except for Lily seems to be down with. My seat-mate, Plane Paul was on the 3rd book of the series so of course I had to interrogate him about his opinion. He had also booked his ticket last minute because he had to shore up some real estate sales and cut his vacation short. Fast forward four bourbons later and we’re making out, trying to navigate the massive armrest while dodging looks from the judgmental flight attendants. Apres flight, I offered him a ride home and lo and behold he lives at a house that Lily and I had attended a birthday party at several months prior. 
  • App Man: Networked by another friend of a friend to help facilitate development of an app. A few endearing phone meetings leading up to a suggestive in-person rendezvous has me reconsidering my strict no fraternization policy…


  • The Felon: From December through mid-February, he had previously been referred to as “Favorite Affiliate” until he stopped deserving such an endearing term. We met initially at Jake Gyllenhaal’s house and he is the only person I have been so intensely attracted to at first sight. He lived in a desolate part of town, didn’t care about things like having an e-mail address, and always felt the need to re-iterate to me his “simpleness.” He was also the only person I have ever felt like I could be capable of orgasming with though we never had sex mostly because I was sure I would catch even more intense feelings. To verify the name, he had gone to prison for a couple of years in the past for reasons I am still unclear on and he did seem to have a temperament that would alternate from aggressive to sweet and caring. In all honesty, The Felon warrants an entire post since he is the only affiliate from my past in which it still stings to see his name. Things ended very badly to say the least and I still stress about how I will react the next time I run into him. Also worth noting: I did not so much as air kiss a single affiliate during the time period that The Felon and I were seeing each other. 
  • The Third Housemate: Third housemate is in our extended friend group and lives with Jake Gyllenhaal (my most recurrent affiliate) and The Networker (who I briefly dated though never got physical with). Recently, Poppy and I had been out with all of the above, Jake Gyllenhaal had dipped out (presumably for a booty call) and left his housemate behind. Me, being philanthropic accepted his request for a ride home still unclear on whether he was attempting to hit on me or not. You see, third housemate possesses an extremely business-like demeanor and doesn’t beat around the bush with his out loud thoughts. I also have made him laugh multiple times so I figured he must think I’m at least SORT OF cool but also figured he would not try anything with me since I was just at his house two weekends prior sleeping over with Jake Gyllenhaal. Lo and behold, I stop in front of his house, he asks me to park and and then full on lunges a vicious make out session that made me feel like how post-Couture patrons treat their C Burgers. I then make the poor decision to go upstairs with him thinking Jake G would be with some chick and of course he’s just chillin in the living room ALONE adding to what may be one of my most awkward experiences to date. Long story short, third housemate and I hook up, he THANKS ME to which I respond by laughing, and I sneak out sometime before dawn once I hear him snoring…and I leave a $300 Dolce & Gabbana blouse behind after giving up from two minutes of frantic searching. I am still on a quest to re-acquire the shirt.

NOTE: In the time period since the last post I have continued to mess around with Jake Gyllenhaal on occasion and i did finally make out with Scott Disick Junior. 

spacemanjr asked: What are your favorite places to shop? Girls and guys.

We all do a fair amount of online shopping due to Portland’s rather limited repertoire, so for that reason we’ll provide our favorites in Portland and our favorite e-retailers:

In Portland:

  • Nordstrom (sort of obvious); we’re suckers for the new Savvy and via C sections as well as the fact that this is one of the few places in Oregon where you can purchase Alexander Wang, Proenza Schouler, and Chanel.
  • Mario’s: Actually better for menswear in my opinion, however they do have a limited selection of Louboutins and I once got a beautiful Elizabeth and James frock from there.
  • House of lolo: Adorable boutique with the best dresses! Around 31% of Danielle’s wardrobe is from here.
  • Solestruck: Duh. We have to pick Portland’s signature shoe whore mothership. Plus they really do have some incredible stuff.
  • Anthropologie/Urban Outfitters
  • Kate Spade
  • Leanna NYC
  • Moulé
  • Aritzia (There is one at Washington Square Mall in Tigard)


  • Zara
  • Stylemint (We swear that everything looks WAY better in person than on the site)
  • Asos
  • Neiman Marcus
  • Net A Porter
  • ShopBop

If you’re just wondering about designers we like, here are some of our favorites:

  • Elizabeth & James
  • Alexander Wang
  • Oonagh by Nanette Lepore
  • Helmut Lang
  • J Brand, James, Ksubi, Rag & Bone (for Jeans)
  • Stella McCartney, Wolford, La Perla, and Hanky Panky (for lingerie)
  • Lululemon (we do do yoga after all…)
  • Theysken’s Theory
  • Herve Leger
  • Christian Louboutin
  • Black Halo
  • Trouvé (only available at Nordstrom)

The Essential Guide to A Socialite’s C-List To-Tap List

Since this is Portland, any “celebrity” here is C-list at best (with a few minor exceptions of course). Any To-Tap list should contain potential affiliates for each of the below categories:

  1. The Chef (line cooks don’t count. If you need any inspiration, chefs are people like Gregory Gourdet and Jason French…there you go, now I’m sure you can think of someone)
  2. The Craft Cocktail Bartender
  3. The Fashion Designer (Gerard may be the only one who is able to accomplish this one)
  4. The DJ
  5. The Rapper
  6. The Non-Rapper Lead Vocalist
  7. The Blazers/Timbers/Winterhawks Player
  8. The Young (ish) CEO (Preferably of a PDX-based startup)

Anyone we’re missing? 

So Poppy and Lily are off to meet Danielle in Fiji. Be back on Sunday…be good, Portland and don’t do anything too fun without us ;)

Palate Cleanser: The politest way one can refer to a brief yet sudden rebound.


The List of Acceptable Places To Be Taken to Dinner By An Affiliate who has Pissed you Off

*This post was inspired by recent events concerning Poppy and her presumptuous ex. Penned in collaboration with Lily. 

  1. Beast: It goes without saying that the wine pairing is a mandatory addition to this typically $75 pre-pairing meal. This also will most likely require some sort of pre-planning and may result in some sort of public overhearing of your couple issues since you have no choice but to be at a communal table.
  2. Le Pigeon: Any smart affiliate would take a lady he’s trying to re-impress here…Lily even says that she would give The Felon another chance if he bought her dinner at Le Pigeon and I told her I would unfollow her on Twitter if she ever gave that bastard another shot.
  3. El Gaucho: You bet he better have worked several days just to fund the eighteen minutes of satisfaction that slab of filet mignon will bring. 
  4. Roe: Because not even I have managed to snag a reservation there yet and their menu is a melange of foie, lobster, and everything nice
  5. Bamboo Sushi: Might as well splurge on seafood charcuterie and fancy sake if it’s on someone who pissed you off’s tab. Also Lily says one of the bartenders is hot. 
  6. Genoa: I’ve never been there but it was the first search result when I googled ‘Most expensive restaurants in Portland’
  7. Departure: Mostly because I have a crush on Gregory Gourdet, adore the ishiyaki steak, and can wear Herve Leger and Louboutins and not feel like a social pariah. 
  8. Laurelhurst Market: An obvious choice as this might be our favorite restaurant in the city; just make sure that I get to have rose with my oysters, an impeccable Pinot Noir for my slab of Teres Major and the Smoke Signals cocktail for when they slip up and say something that might pinch the wrong nerve. 
  9. Noisette: It’s cute, little, and French and costs more than Beast. 
  10. Portland City Grill: We all despise PCG and merely think of it as the place that people from LA with generic palates go to so really this would be the choice to select if you want your wrongdoing affiliate to suffer at the fact that they would be sacrificing several hundred pretty quarters on a subpar meal. 

Everyone I’ve Ever Had Sex With: Gerard Edition

Gerard being an extremely competent male socialite took the time out of his busy schedule to pen us his personal juicy list inspired by Nerve’s ever so popular column "Everyone I’ve Ever Had Sex With"

If you are a Nerve reader, I am sure you have picked up on the fact that we get a lot of inspiration from their posts. In any case, enjoy. 


Sloppy. We were both seventeen and had acne. I had just gotten back from band camp. We got off awkwardly and easily from some heavy petting and now I’m repulsed by any physical evidence of lingering baby fat in all men. I haven’t talked to him since high school ended, but I’ve heard he’s dating the most annoying girl I’ve ever met.

A beautiful, beautiful man by any standard. He was a model for some kind of gay colony that establishes itself during Burning Man. He was the first hookup of my college career. He went to school in Washington and was visiting a friend; he didn’t see that friend for the entire weekend he was here. We hooked up in music building on my alma mater’s campus. He showed me the wonders of a skinny white boy’s body. I crushed way too hard and experienced my first ever heartache.

So far below my league, an occasional coke addict. In fact, I stole him from a local coke dealer from around my hometown. I’d been crushing on him since high school when he was a baseball player. He had gone to seed by the time I got there, and his facial hair scratched me up every time we hooked up. But he was my first full-on gay sex partner. We fooled around far too much in his Mazda, which he loved more than me.

A disaster. He has since revealed himself to be a really negative, catty drama queen. At the time, he had been pining after me for some time and eventually I gave in because persistence and horniness are all you need in most sexual situations. He had the body of an anorexic snake. I have since stopped talking to him and he is consistently mean to me.

He has slept with an astounding number of people and was thus gave me my first STD-related freak out. I never caught anything from him and he never had anything to begin with, but the whole experience made me a bit paranoid. But so damn handsome despite his stupid facial piercings. A self-proclaimed party boy living in San Francisco, he still drunk texts me sometimes.

Quite possibly insane. Beautiful and insane - like Fiona Apple status. He carried around a large plastic flamingo named Washington and has an unfeasibly large penis. Calls himself a performance artist and quasi-cheated on me with an equally tall and gangly blonde number who is, in my humble opinion, vastly less attractive than me. But I didn’t let that stop me because this occurred during my “no self-esteem” phase. He currently resides in Ecuador where he studies accordion music and composition.

An eternal gay-by (as in “baby”), the ingenious term I learned from a friend. In other words, he knew nothing about and was very uncomfortable with his sexuality. I was the first guy he’d hooked up with and he got very attached very quickly. I still feel guilty about making out with the next guy on the list in front of him. In a movie theater. In the seat next to his.

My first official boyfriend. An artist and brother of a band member of a fairly popular band. So sweet and so kind. Things fizzled out and, to my peril, I lost interest. We had sex on coke a few times and he cut his own hair to mixed results.

We’re still close and still in contact. The first time we hooked up was after going to a club in West Hollywood. We were in his car. He had taken a fair amount of Benadryl. He tried to make me get myself off while he was driving down the freeway several miles above the speed limit. I politely declined. We next hooked up in his hotel in downtown Portland after an art opening. I anticipate round three is in the near future.

N-E-U-R-O-T-I-C. Stalked me. He’s very cute so I was more okay with it than I should have been. Then he told me things were moving too fast after we hooked up soon after said stalking. I wrote the angsty only poem I’ve ever been proud of after the mess ended.

Saddest sack of all sad sacks, which I am admittedly quite attracted to. It was nice, but I never got very close to him because of aforementioned sad-sack-ness.  

One of my good friends. There’s nothing romantic between us now, and he’s seeing a 20-something in the restaurant industry. It was not really sex, but we did mildly hook up while I was fairly drunk and he had taken a couple Ambien and drank a box of Franzia. He does not recall the night in question.

We haven’t had actual sex, but a fair amount of virtual sex. He worked for the school I attended whilst abroad. All the girls were crushin’ but once again Gerard claims the day. He admitted to having a thing for me after I’d left the country, which was lame but allowed for intimate Skype sessions.

Another sad sack with whom I entered a relationship prematurely. He’s a performer who I believe is meeting success in his field nowadays. I’m happy for him, and still feeling bad about dropping out of contact with him. But there wasn’t much I could say because of the next dude.

By and large the most fucked up relationship of my life. It wasn’t really a relationship so much as an extended exploitation. Taught me a lot about myself and shook me to my core. I thought I was unmovable and invulnerable to the crazier side of romantic emotions, but oh man was I wrong. I am so much stronger for it’s having happened, and so much happier for it’s having ended. I really wish him the best because he will not meet with success in life if he continues the way he is.

Has already made an appearance in a previous post of mine. Cute sweetheart with questionable fashion sense who I’m not into at all and with whom I had no sexual chemistry. But I believe he’s still single, gentlemen. You could be the one.

First Date Chronicles: L8r H8r

And we present to you…another guest post from the ever so eloquent, Gerard:

One of the longest romantic entanglements of my life was conducted almost entirely through text messages over the course of six months. I don’t know if this is a sign of the times, or whatever, but I’m nothing if not a 21st-century babe, so reserve your technology prejudice, haters. 

Like many Portland events, it all started at Stumptown. There I was - drinking an iced americano, re-reading the same sentence over and over again in my book when I got that spooky “someone is looking at me” sensation. Lo and behold, there he was: blondish, crooked smile, wearing a large patterned scarf indoors over his t-shirt. “Faux pas,” I thought to myself. But that crooked smile was pretty endearing, and it was fixed on your boy, so what the hell. I then engaged in the first and only successful significant-eye-contact flirtation session of my life. In procedural terms it went something like 1. look up, 2. smile, 3. look down, grin at self, 4. look up but avert eyes, 5. look down, pretend to turn page, 6. more eye contact, 7. look back down again. Pretty gross, I admit.

Feeling flustered from this heavy eye contact, yet not really invested in the dude (generally cute, but not really my type), I packed up my things while he went for a refill. I snuck off to my car, but as I was trudging away, someone yelled “Hey!” Of course, I knew exactly who it was. I prepared my best “Who? Me?” expression and turned. Lo and behold: number in hand was my would-be, staring contest paramour. The note said “Call me sometime, you’re cute :) XXX-XXX-XXXX.” Ever the master of awkward-disguised-as-aloof, I just thanked him, smiled, and drove off.

I held onto his number in my wallet about a week. I hemmed and I hawed. I was in the middle of writing a thesis, but hey, the stakes were low. Ever the coy bastard, I texted him to see what was up, asking if he recalled the previous week. Of course, he remembered me. Following an hour-long text session establishing basic affirmations that neither of us were serial killers, we set up a date: beers at his place. Well, the date came and I was feeling under the weather and couldn’t make it. At this point, I wasn’t feeling too jazzed about the whole situation and didn’t really follow up for a raincheck. My perennial “I’m writing a thesis” excuse was quite overused at this point, but hadn’t lost its efficacy. Thinking he would get the point and that he obviously wouldn’t have been very invested either, I didn’t think much of it.

I proceed to receive weekly texts from him - mostly multisyllabic “heyyyyyyy”s and non sequiturs. I respond at first, but never alluded to wanting to see him. Because, you know, text conversations are surprisingly eloquent. Sometimes people say that it’s SO HARD to tell what people mean when they’re texting. I’ve never really had that problem. Because really, it’s not that complicated: emoticons are always flirty, but occasionally platonically so. Extending letters is an attempt to be casual in situations when you don’t want to betray being desperate. Perfect punctuation and capitalization means they’re thinking too hard about it. Total lack of punctuation and excessive abbrevs are a dealbreaker. So as far as this encounter goes, the dude was fairly textbook. Hating straightforward actions of any kind, I was of course turned off.

It all came to a head, though, when the phone calls and texts were every other day, then every day. I once had a vaguely stalker-ish figure in my life, so at this point I was on the defensive. Ignoring him wasn’t working, and the whole thing was weirdly intense despite being conducted mainly through text message. I mean it was hilarious, sure. But homeboy couldn’t take a hint. And so I drafted the most straightforward text message of my life.

            “K——-, I have no interest in meeting up with you at this point or at any point in the foreseeable future. This is quickly deteriorating into a really pathetic situation. I have been patient and I admire your determination but this is not fair to me or to yourself. Do not call me. Do not text me. Go back to Montana. Stop.”

I regret being mean at the end there, but at that point subtlety was failing me, which was distressing in and of itself seeing as I am eternally ambiguous and strive to cultivate an air of mystery. I’m sad to to say that at that point I was so riled up that I really wanted some kind of violent reaction. But all I got was “ok, sorry to bug you.” I mean, come on, at least let me feel like I have some sort of impact in this situation! But no: utter calm. Which of course made me even angrier because I thought I was being beaten at my own game. Being aloof and unconcerned is MY THING. But, you know, a graceful 21st-century gentleman should recognize when to check his pride and realize that sometimes the satisfaction of eliciting a response from someone - showing that you have power in a situation - sometimes is just caddy and perpetuates the idiocy and immaturity that you try to avoid. Which is why I really regret responding to that text with a picture message of me flipping him off.