The Crush Letter No 112

I'm Dish and I write a weekly newsletter about life, love, and culture for those 40+. Because midlife and beyond is so much cooler than they said it would be. Hell yes, sign me up for the Dish.

Hello Crush,

Happy Saturday morning. Well, we're solidly into Spring and it feels good, right?

Thanks to all those readers who sent love, sympathy and encouragement to me after reading that I was getting back on the dating apps. And of course, there are those of you who just say no to the swiping: "I STILL can't bring myself to venture into the online dating apps," wrote one of you. And it's already been DRAMATIC, after only a week. Even though I'm trying to be the ocean. Like that Leonard Cohen quote "If you don't become the ocean, you'll be seasick everyday."

But given that I am spending so much time swiping and texting, I thought I'd dive back into the subject of sexting. In Part 1 (a while back) I wrote that sexting is its own language.

"If you think of sexting as simply shooting over some dirty talk or an explicit photo by text, you’re not thinking big enough. What it is really is an additional, unique mode of verbal communication. And we need as many modes as possible to stay connected. For the obvious reason that sometimes one works better than another to get through (or get by, after a conflict).

In truth, I think the term "sexting" is too narrow to capture the full potential of this communication style - texting intended to establish and maintain closeness - since many of the techniques that work best for sexting apply, of course, to any non-sexual text with your closest friends. I think something like "intimate texting" is a more accurate descriptor of what I’m trying to master, though admittedly not as catchy."

Here we go with Part 2.

Before we get there, one of our diehard PrimeCrush readers wrote a very personal TOPIX, which floored me. It is an intimate, super honest account of his relationship with monogamy and it includes some revelatory admissions, not to mention his original love/lust theory. I think you'll find it compelling. I did.

And there's much more in this week's Letter. Enjoy!

In This Letter. +TOPIX: Embracing Hetero Monogamy at 57. By “Kevin Cox” My entire life I ran from monogamy. +Tell Me More: Dish’s Personal & Practical Tips for Sext Mastery - Part 2. Good sexting is really just showing you’re interested–especially interested–in your sexting partner. +{Re-Share} Tell Me More: Dish’s Ode To Sexting. By Dish Stanley Part 1 of 3 Sometimes there are things you very much want to say – or should be saying – that you just wouldn't ever say in person. +Social Media I Loved This Week. By Dish Stanley +Our Song of the Week I’ve been playing out a lot of hypotheticals in my mind

TOPIX: Embracing Hetero Monogamy at 57. By “Kevin Cox”

Midlife has always been that point when we begin to realize that life is getting short. Too short to worry about what other people think. A turning point where people begin to craft the kind of friendships and romantic relationships that actually work for them, inside the lines (or out). TOPIX is our way of getting opinionated, courageous conversations started on what living and loving really looks like in midlife now.

“For the longest time I have had a theory about this phenomenon, which, I am sure, many of you out there will dispute, but I stand by it. It’s my love/lust theory.”

My entire life I ran from monogamy.

One way or another I did not embrace any of the theoretically monogamous relationships I found myself in. If I wasn’t cheating, I was obsessing about cheating, or about upgrading, getting out of the relationship I had currently found myself in, and finding someone else.

But just recently I have learned the joys of embracing monogamy. And I think my story may serve as valuable insight to the many men — and perhaps women — who have found themselves in a similar predicament.

But we need to go back before we go forward. I married late in life. I was 37. Part of that, no doubt, was my issue. I could not commit to a partner. But pushing 40 I was ready to — more subconsciously than consciously — settle down and start a family. So, I settled on a partner in order to settle down. I did not marry the love of my life, but rather, married the woman I happened to be in love with at the time. Not surprisingly, it was not a good fit. But I soon had children, finally, and I was happy with most aspects of my life (my job, my kids, my house) just not my partner.

Seven years into that marriage I had an affair. I fell deeply in love with another woman. That soon led to divorce, but, like a lot of affairs of this type, that relationship was not a great long-term fit either.

Now single and in my 40s, I found the freedom and sexual renaissance I had been seeking since I was 13. I had finally come into my own as a sexual partner, tons of women found me attractive, online dating had exploded onto the scene, I traveled often for work, and I could not become emotionally attached to any one woman even if I wanted to.

Let’s go back in time again. I was young for my class when I went to boarding school as a freshman, and my formerly all-boys school was in its first year of co-education. We had 50 boys and just seven girls in our class. In my mind, with so few girls to pursue, and nowhere else to turn, I spent my high school years over-aggressively chasing the opposite sex and feeling rejected when that didn’t work. I felt that no one wanted me. So when I found myself to be something of a hot ticket in my 40s, the pull was irresistible. I was the guy who could not say no.

Continue reading here

Stay tuned to this continuing series. Got a TOPIX? Write to me! Dish@PrimeCrush.com.

Tell Me More: Dish’s Personal & Practical Tips for Sexting Mastery (Part 2 of 3)

In Part 1 of Tell Me More, Dish shares an ode to sexting and its many uses, including how to make up after conflict. If you're new to it, we recommend you also read Foria’s ‘Totally Useful Guide to Sexting’ to get the 101’s of establishing expectations, consent, checking in and agreeing on what can (and cannot be done) with your sexts after the fact. Here Dish reveals more about her personal style and shares some sext snippets and sensual words to inspire your own sexting.

Start with Part 1 of Tell Me More: Dish’s Ode to Sexting {Reprinted in its entirety below}

Good sexting is really just showing you’re interested–especially interested–in your sexting partner. As I shared in Part 1 of Tell Me More, there are as many ways to be great at sexting as there are to be a great communicator generally, or for that matter to be a great flirt. You can call it a form of foreplay or you can simply think of it as a way to flirt using a lot of short, poignant words that takes your partner's preferences and attributes particularly into mind. It is not just for millenials, it need not be raunchy or even particularly explicit so get that formulaic thinking out of your head. Sexting – like other ways of showing you care for someone – is a superb additional form of expressing an interest.

Remember this from Part 1 of Tell Me More:

Think about the receiver (“your partner,” for these purposes) very specifically.
What do they do/like/feel proudest of about themselves and/or their bodies.
What can you think of with specificity that you’ve done together? What did they laugh at, enjoy, not like?
Pay close attention to how they respond by text–single words/one-liners or extended paragraphs–and consider whether you want to mimic them (to create or keep a rhythm going or want to break that up (to create abrupt excitement).
Notice whether they use visual words, sensual-sounding words, lots of active verbs or straightforward nouns. Those are clues to what they like “sextually” (and probably other things about “their language” for all kinds of communication).

Use:

The ellipsis (“...”) to strategically leave something to the imagination, catch a breath yourself, let your partner catch a breath or to create anticipation.
A strategic pause — maybe followed by “ahhh, had to catch my breath” — to create tension.
Words like "ummmmm" and "hmmmm" when you want to be more suggestive than explicit.

If you don’t know the person you’re sexting well, of course that means asking what could be an increasingly intense series of “what do you like” or “would you like {offer a suggestion}” series of questions. It could go like this:

“Imagine we’re sitting at a corner table of your favorite restaurant. How would it feel if I gently brushed my hand against your leg?”

And then it could be “Oh, you like that, huh? What if I rested it there for a bit, and then traveled up? And rested it there for a bit and… Well, you get the gist of where I’m going.”

You might want to test out whether they prefer for you to be the more graphic one or whether they want to get in on the action by saying: “And when my hand got hot, I mean really hot, what would you want me to do?”

Of course the above questions work just as well for somebody you already know. But if you know them — if they are a long-term partner, then you want to get very detailed about them. Here are some tips:

Compliment/talk about their characteristics (physical or otherwise) very specifically:

Say: Your skin is as pale and smooth as those leather gloves you put on to drive the golf ball, and I love how sensitive it is when I start running my fingers across your inner thigh. You twitch ever so slightly when you’re turned on.

Rather than: I love to touch your big cock / juicy vulva.

Say: I love how I can tell that you’re getting turned on by the way your breathing builds up, from deep and full to hot and needy. When you rolled me over I swear you were panting. Hungry.

Rather than: I love it when your hard cock gets so hard / your juicy vulva gets so wet.

Say: You tasted creamy and rich and tart and kinda sweet, kind of like the key lime pie we had in Sarasota last winter.

Rather than: I love your sweet cum.

Say: Let’s start by imagining that we are putting on some Marvin Gaye. Because I know you love Marvin Gaye.

Say: I picked up the sexiest, most literate collection of short stories I could find. Because I know your favorite thing is for me to read you very well-written smut. Here’s the first line: …

An exception to the “sext as an improv collab” (and a favorite type of sext personally) is the "drive-by sext” — where a reply isn't expected or required. It’s a powerful way to tell someone they are wanted while minimizing disruption, not imposing on them if it’s a bad time for them to sext back or just giving them the space to consider.

Reminder: Expectations. Sexting is asynchronous. When you’ve just “opened up a sext line” on your end, you never know what someone has going on in the moment on their end (work crisis, bad personal news or in line at the grocery store). You don’t know who is around them (professional colleagues, kids). Starting it up, it’s best to think of it as a “send it out, expect nothing back” thing. By all means try not to take it as rejection if they don’t respond quickly, or even that day. Just because you were in the mood in that moment doesn’t mean it was a moment that worked for them.

As the recipient of a sext that comes at a bad time for you, a good practice is to reply when you can with a simple: “Thanks for that - thoroughly enjoyed - caught me in a meeting and now I’m on the run.”

A great sext for extended foreplay is the “what you’re going to do to me / what I’m going to do to you” next time I see you sext.

A variation of the above is “what I did to you / you did to me” sext.

In Part 3 of Tell Me More, I’ll be offering examples of sexting scripts and sexy words to get your imagination flowing.

Did you know that there’s an app specifically for sexting? Amorus is a relationship intimacy app that provides tips and games to encourage more skilled, creative, and private sexting. We “hooked up” with its Founder Elizabeth Dell, read more here.

Other articles in our sexting CRUSH Letter spell out the 101’s of sexting: establishing expectations, consent, checking in and agreeing on what can (and cannot be done) with your sexts after the fact. We recommend you read Foria’s Totally Useful Guide to Sexting to start. Here Dish reveals more about her personal style and shares some sext snippets and sensual words to inspire your own sexting.

Dish’s Ode to Sexting

I love sexting. Giving it thoughtfully and receiving it joyfully, like it's a heaping bowl of creamy carbonara that we're sharing by handing it back and forth until we’re both sated.

It's its own language.

If you think of sexting as simply shooting over some dirty talk or an explicit photo by text, you’re not thinking big enough. I prefer to look at it as an additional, unique mode of verbal communication. And we need as many modes as possible to stay connected for the obvious reason that sometimes one works better than another to get through (or get by, after a conflict).

But in this piece let’s focus on the sexy text.

Can't Say It? Sext It.

Sometimes there are things you very much want to say – or should be saying – that for whatever reason you haven’t (or can’t) say in person or over the phone. (Like suggesting certain fantasies.) Or on the flipside and just as importantly - there are things you might think it would be easier for your partner to receive by text (because they’re less on the spot, get some time to pull their thoughts together before responding). The fact that it can be either asynchronous or synchronous (an active, engaged collaboration in real time) is, in my view, its great advantage. In one mode of communication, you can have the potential for immediacy and intensity, or the option to take time to pause and consider a response.

It’s in part because of this that sexting can allow you to be bolder, more daring or revealing or vulnerable than you’ve been able to be (at least with that partner) in person. You might find this surprising, but I'm kinda shy about live kinky talk. I’m working on that, but in the meantime I can initiate by sext things that are hard for me to say live. I'm still not very lewd by sext. I've never sent a nude pic, and don't want to receive any. Many who excel at sexting have a lot of fun with raunchiness. I applaud the bodaciousness, but truthfully I am more apt to want to get things started that will continue IRL (or pick up the phone) when it gets to that stage. Yet even without some of these more explicit things in my “sexting practice," it has had true, distinct value in letting me step out and be more daring (and vulnerable), all of which leads to my ultimate goal of creating greater intimacy.

The Reconnect Sext Is Often the Boldest Sext of All

Another really important relationship area where I’ve been more daring by sext than in real life is re-establishing closeness — or maintaining some thread of proximity — after an awful fight.

Other Useful Sexting ("Can't wait!")

A sext can keep things close with your partner while one of you is on the road; light up your (or your partner's) masturbation session or introduce a fantasy in a safe, low-key way. It can be foreplay — on a scale of warming things up to turning it on, and you can make it as hot as you want to start it out, and take it as far as you’d like to go.

I almost always send a sext of some sort to rev things up before a date (if it’s the first date, “can’t wait” or “really looking forward to meeting you in person to hear more about {your writing/son’s ski race/etc}” is enough. And it can be the difference between starting things IRL at a cold versus warm temperature.

I love the art of the sexy compliment, and of teasing. I am into a sensual "drive-by" sext (eg, no response required or expected) as a high-impact way to give my partner a shot in the arm without disrupting his day.

And it goes without saying that sexting has as important a place in intimate relationships that are just beginning as it does in ones that have been in place “forever” and through all kinds of things. I’d argue that good, thoughtful sexting is almost more critical for long-term partnerships — as a reminder that you appreciate and adore them (and don’t take them for granted), or as a post-conflict ice breaker.

Sexting is all-around highly useful and way under-utilized, so in Part 2 of Tell Me More we’ll dive deeper into some techniques and real-life examples from my life, as I’ve worked on mastering my own art of the sext. But here are the basics you need to know:

Basic Techniques & Tips

Good sexting is really just plain showing you’re interested, especially interested, in the person receiving your sext. There are as many ways to be great at sexting as there is to be a great communicator of any sort, but the “improv” model is apt:

Sexting is a collaborative act where the first rule of thumb is to take what your partner gives you, observe it closely, build on it, then volley it back.

Keep your partner specifically in mind:

think about the receiver (“your partner” for these purposes) very specifically
what do they do/like/feel proudest of about themselves and/or their bodies
what can you think of with specificity that you’ve done together - what did they laugh at, enjoy, not like
pay close attention to how they respond by text - single words/one liners or extended para's and consider whether you want to mimic them (to create or keep a rhythm going or want to break that up (to create abrupt excitement)
notice whether they use visual words, sensual-sounding words, lots of active verbs or straightforward nouns - those are clues to what they like “sextually” (and probably other things about “their language” for all kinds of communication

And here are some general tips:

the ellipsis ... to strategically leave something to the imagination, catch a breath yourself, let your partner catch a breath or to create anticipation
a strategic pause — maybe followed by “ahhh, had to catch my breath” — to create tension
"ummmmm" and "hmmmm" when you want to be more suggestive than explicit

The very best, sexiest words are “yes” (or “yesssss”) and “thinking of you.” Everyone loves to hear those. So if you can’t think of anything else to say revert to those, or some variation of those. They are the heart-and-soul and ultimate vibe of the sext. I include a list of sexy words and phrases in Parts 2 and 3 of Tell Me More but remember “yes” and “thinking of you” go very, very far.

But the most important thing to remember, and what makes sexting so powerful as a medium is that it is its own communication mode and it’s so much more than just sending a dick or tit pick. It’s a way to encourage intimacy — whether that is sexual intimacy or just saying sorry to your partner (or a best friend) after conflict.

A place to share loose thoughts & stray ramblings on what's happening.

Beautiful, inviting and finely curated, gotham is the cannabis store we needed.

I checked out the buzzy new store gotham on its opening day this week. And wow! I predict you're going to be hearing a lot more about this concept cannabis store in the East Village. Not only because it is one of the first stores in NYC to get a license to sell cannabis from the City's Office of Cannabis Management, but because it is a beautiful, sophisticated, upscale and cultured experience. Think Apple store meets John Derian meets Butterfield Market.

Founder Joanne Wilson is a retail veteran who knows how to put together all the pieces, from the visual space to the merchandising to the marketing. For anyone interested in her exhilirating journey in pulling her gotham project together, including being among the first to score a coveted cannabis license, Wilson shares her twisty story here. I had invested alongside Wilson in a very early cannabis start-up based in San Francisco almost seven years ago, so I know firsthand that she has been passionate about the space as an early mover.

gotham is as much a lifestyle and culture offering as it is about selling a well-curated selection of cannabis products. Walking into gotham feels like the pop of de-corking a fine bottle of champagne: fizzy, bright and electric with possibility. The staff is enormously friendly and well-educated about the cannabis product line. One shared a story about her trip to visit Marijuana Farms New York, one of the lines from an upstate farm that gotham carries. Everything gotham carries is premium, small-batch and artisinal, which makes the exploration of new products feel safe.

I went home with a lot of wonderful things to try, including the exquisitely packaged pre-rolls from Drew Martin (I am trying Be Bright and Be Open, because who wouldn't want to be?), and a selection of gummies from rose (delights and 1:1) and mfny (tangerine fritter (for arousal) and pillowtalk (for sleep)). I can't wait. Finally, a place where we can shop for cannabis that feels like it is designed to include cannabis users of all ages. gotham is an inviting place that I'll be going back to.

A closer look at the some of the gotham products.

I Don't Know How I Missed Easy, a drama-comedy series based in Chicago about real people in realistic love, sex and relationship scenarios that came out in 2016. But damn, I am enjoying it now. Quirky, immersive, funny, authentic, it tells the awkward and beautiful relationship stories of a series of people who feel real. The opening episode humorously and honestly confronts the fading sex life of a long-married middle-aged couple with kids. A recurring theme is the altogether common phenomenon of losing yourself - your sense of identity, interests, friends - after merging with another. I love this series all the more because it eschews the ubiquitous "rom com" picture of love, sex and relationships and instead reveals stories of love that help us realize that we've got is the real thing, afterall.

The 3rd Season of The Great Is Out. And I haven't watched it yet, but the trailer is delectable.

@devonshireofpalmbeach

@unapologetically_unattached

@markmanson

@charliemackesy

Song of The Week

Hypotheticals By Lake Street Drive

I am still in the early days of my go at online dating this time around, but already I've found myself right where this song is.

Obviously, we're at the beginning of something ...

And I just thought you should know

I've been playing out a lot of hypotheticals in my mind / I've been writing your name down next to mine / Been imagining all the things you and I could do ...

It's so easy to run away with things at this stage.

Lake Street Dive is a 2004 band that comes out of the New England Conservatory of Music in Boston. Influenced by classic jazz, 60s soul and rock and roll, you can hear it all in their songs. In addition to originals, they have done some great covers - Rich Girl is a favorite.

But right this moment I am stuck in hypotheticals, in song and in life.