The Crush Letter No 153: Henry Lost His Dog, What Lydia Is Crushing On, Ask Dish

. 15 min read

I'm Dish and I write a weekly newsletter about life, love, and culture for those 50+. Because midlife and beyond is so much hotter than they said it would be. Hell yes, sign me up for the Dish.

Hello Crush,

Happy Easter!

Bunny's jumping with joy!

In This Letter. +My Friend Henry Lost His Dog. Will He Ever Love Again? By Dish Stanley Now he’s a widow too. A dog widow. +Another Podcast I Listened to While On My 17 Hour Flight from Auckland, NZ to NYC. By Dish Stanley On Marriage, from a divorce lawyer. +3 Things I'm Crushing On. From CRUSH Reader Lydia* Spring Edition! +Ask Dish: Answers to Your Stray Questions No, no, no, no. I didn’t have sex with them. +Social Media I Loved This Week. +Our Song of the Week I won’t fear love

My Friend Henry Lost His Dog. Will He Ever Love Again? By Dish Stanley

My friend Henry’s dog Hogan died.

It happened last week, the day after I returned from New Zealand. I knew Hogan wasn’t doing well when I left so I sent Henry a text the day I got back.

”Hi, how’s Hogan? (I’m back from NZ.)” I wrote.

”Hogan passed away,” Henry responded. “It was his time.”

“I’m so sorry! When? You took such good care of him.“ I replied.

“Yesterday,” wrote Henry.

“Oh gosh. Can I take you out to dinner tomorrow or Sunday?”

“Sure. Dinner Sunday.” (He’s taciturn. More on that later.)

But let’s back up. Let me tell you about Henry and Hogan.

Henry and I are platonic friends but I originally met him last April through the online dating app Bumble. He is first rate. I mean absolutely first rate. He has all the character qualities you’d want in a romantic partner (or friend) (integrity, kindness, self-awareness, a good sense of humor - I could go on) and all the other traits that characteristically draw a long line of potential female romantic partners (he’s tall, wealthy and swears he’s a great cook). (I’m sorry to be so blunt but there’s no point to this whole exercise if I’m not going to be honest.)

Despite all that, inexplicably and unfortunately, I didn’t have romantic feelings toward Henry. “Would you consider a friendship?” I asked.

“Sure,” he said after an awkward, lengthy pause. “You’re the most interesting person, male or female, I’ve met in a decade. Let’s try.”

“Thank you,” I said.

(As a related tangent, I was on Bumble for one week last April. After a lot of sifting, I ended up meeting two men IRL. They both turned out to be really excellent people. Utterly first rate. A year later, I am friends with both of them. More on that, if you’re interested, in “Ask Dish,” below.)

A couple weeks after Henry and I agreed to try to be friends, we were going out to dinner. He had made the reservations and called to tell me how to get there. “It’s tricky to find. It’s a tiny Italian place and the chef cooks straightforward red sauce Italian for five tables of two a few nights a week, and you‘re served whatever he is cooking. By the way, you eat everything, right? When you get off 95, you know how if you go left you see a small unmarked road? You go down that …”

”Ummm, yeah, this is not going to work out,” I laughed. “I mean, I do eat everything! But I get lost going to my own bathroom,” I admitted.

“Right. Come to my house then. It’s easy to find, and I’ll drive.”

As he was letting me through the front door, Henry said “That’s Hogan on the floor. He’s 14 and having some issues getting around, so Tracy comes to do acupuncture treatments on him once a week. ”

Tracy administering acupuncture on Hogan. (And that’s not my leg.)

As we headed out to dinner, I pointed to something that looked like a super-duper high-tech mini bed, placed in front of the floor-to-ceiling window next to the front door. “Wow. Impressive. What’s that?” I asked, pointing to the whole get-up.

”Henry likes to sit in front of that window in order to see what’s going on, so I had that bed installed for him. I put in an electrical outlet so it could be heated because it’s more comfortable for his arthritis.” 

I put my hand on it, and sure enough, it was ever-so-tenderly-warmed-up. I wish I had a picture of the bed for you, CRUSH Readers, but I’ll just say that it was lined with a soft pile and was so comfortable looking that I was tempted to skip out on the ”secret IYKYK Italian place” and crawl into Hogan’s bed right then and there.

Henry got Hogan when Hogan was two months old. He was named after the great golfer (and gentleman) Ben Hogan. Henry was a Portuguese Water Dog and, unlike any other dog I’ve ever met, instead of coming up to greet (and sniff) you when you entered his home, would stay seated and wag his tail sweetly. He just sort of expected you to go to him, but you could tell he felt sheepish about it because he was raised with proper manners. (It was due to his arthritis, I think, his whole coy thing.)

Here’s a better picture of Hogan.

Henry sent me this picture of him feeding Hogan sushi.

Henry lives by himself. His family lives in Virginia, where Henry grew up (and went to college and business school). Which (to generalize) might explain why Henry is so poised and well-mannered. (I can’t remember ever meeting a guy from Virginia who’s not a gentleman.)

Henry laughs warmly when you say something funny, and also cracks a low-key joke now and then. He listens carefully and acts as if everything you say is important to him (he has three older sisters!), nods as he follows along, and responds in a deliberate, thoughtful way, using the fewest possible words. His manner, even when he talks about Hogan, is stoic and unsentimental.

So when I was at his home the night of the IYKYK Italian dinner and he went upstairs to grab something, I was surprised that Tracy (the acupuncturist) began to bubble over effusively about Henry. “Henry is one of the kindest men I’ve ever met,” she said. “I used to drive an hour each way when I worked for an alternative vet practice and I’m a single mom, so that was tough. Henry suggested I start my own business as a visiting acupuncturist, and then helped me with the company formation, filling out the filings and paperwork and showing me how to do my books. He explained what were deductible business expenses and how to file my taxes. I now have a better lifestyle, get to see my son’s games and make more money. Even after all that, he insists on paying in full for every appointment. Do you have a dog with any aches, by the way?”

We all know men who are deeply emotional but don’t gush (the way I do) about the people they love, their kids, their friends, their partners. Not even their dogs. My brother - who is as stoic a guy as you’ll ever meet (I think I may have mentioned that he was a Green Beret?) came home one day a few years ago to find that his black lab Ranger had died. My mother happened to be dropping off his daughter just then and told me that he burst into tears, got down on the floor, laid next to Ranger and sobbed uncontrollably for a half hour. He didn’t get off the floor for another hour. I’d already heard this startling description from my mother by the time I talked with my brother, and all he said, in a muttering-under-your-breath-voice was “Yeah, he was 15. It was expected.” And I’m close to my brother.

In other words, you can’t be fooled by a man’s cool temperament where his dog is concerned.

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Another Podcast I Listened to While On My 17 Hour Flight from Auckland, NZ to NYC. By Dish Stanley

Well, as you can imagine, I had a lot of time on the round-trip flights to and from New Zealand (over 32 hours of flying time) to catch up on things I’ve been meaning to listen to (and other content). I’m still recommending things I listened to on those flights.

On Marriage, from a Divorce Lawyer.

Listen/Podcast. Modern Wisdom hosted by Chris Williamson: James Sexton, A Divorce Lawyer’s Perspective on Love & Marriage (Episode 3/14/2024 #757)

James Sexton is a divorce lawyer and the author of If You’re In My Office, It’s Already Too Late (2018). I thought this conversation had a couple of good reminders for all of us in or looking for relationships, and an interesting take on prenups for those getting married.

The biggest take-away for me was the importance of developing, early in a relationship, the skill of having hard conversations. None of us wants to have an uncomfortable conversation with our romantic partners - we want to laugh, have a calm dinner, watch a movie together, etc., but having important conversations is an act of love. It is giving the relationship the respect it deserves. The respect of putting the effort and discomfort into doing what’s necessary.

If you want to have a long-term, strong, happy relationship with somebody, you have to be able to say things like “What happened was not okay with me, and I need to talk about it.”

One way to get comfortable initiating these conversations is to take the perspective that our desire to walk into conflict on an issue is an indication of how seriously we take the relationship. One way to get comfortable (and even appreciative) when you’re on the other side is to recognize the show of respect that this effort demonstrates. On the flipside, an inability to discuss difficult things is a red flag that communicates that a robust, healthy relationship is not a priority, not worth the hassle. A successful relationship requires work, you want to see your partner demonstrate a willingness to do the work required of a successful relationship.

Remember that it is so much easier to do the work of staying happy while you are in a relationship, then it is to become miserable with somebody and try to crawl back to happy again. What “do the work of staying happy” means, in large part, is the willingness to address conflict areas early, when they arise.

Pre-nups. Related to having tough conversations, Sexton is an advocate of prenups. Prenups are protective! How do you raise them? Say “We’re going to have to have hard conversations, and I want us to know how to do that. I want this to be forever, if I didn’t I wouldn’t marry you. But if it doesn’t last forever, what do we owe each other?“ Another way of looking at it is that a prenup is saying “I don’t want you to be in this relationship because you’re afraid that you won’t be able to survive financially if you’re not here … a prenup will spell out how we will fairly split assets so that we can each go on if the marriage is not working.”

Love is never permanently gifted, it’s loaned. And that’s a good thing. Continue to put effort into your relationship and walk the line.

Ask Dish: Answers to Your Stray Questions

From the sublime to the ridiculous, I get a lot of random questions. I answer some of them here. Got a stray question? Submit it using this link.

"Hi Dish! I really appreciated reading the responses to the most recent Ask Dish about finding friends to do things with on week ends when you are solo. Follow-up on that. Can you give more detail about the “wonderful, cool men” you said you met while dating but ended up as friends with. Had you had sex with them at that point? How does it work in terms of who pays, etc? Is it really tension-free? Have you ever had a situation where one of the guys you become friends with in this way comes back and says he is in love with you, and can’t be friends any more? I see your point about how they are the most obvious pool of people available to do things with, but I’ve never done this. Thanks. I love The Crush Letter! Cheers, Tricia"

[Here are the relevant portions of my previous Ask Dish response - to bring all CRUSH Readers up-to-speed:}

[I IGNORED the advice that a lot of dating coaches give that you shouldn’t waste your time becoming friends with people you meet on dating apps with whom you aren’t a romantic match. “Focus on the search for your match", they say. I don’t think their advice is targeted to people at our stage, who can find it difficult to find friends to do things with. So, on a few occasions, when I’ve met men with whom there wasn’t a romantic match but we seemed to have the same interests, I asked them if they’d consider a friendship. If you consider who is in the potential pool of people available on week end nights to do things with (so very small), you pretty quickly get to a place where you see that essentially they’re an obvious source, if not the most obvious source, of company. You usually have a sense at that point of whether they were good company and how they like to spend their time. Over the last five years, I’ve made four cool, wonderful male friends this way — with most, I have casual, periodic get-togethers, playing golf or tennis or going out for a drink, dinner or movie. One has become a closer friend … Interestingly, the friendships have endured as/when either of us has found a romantic partner.

Pro tip: For me, in order for this to really work without drama, it has to be super clear that it‘s a “straight-up friendship” because I don’t want to get ‘hung up’ on a friends-with-benefits or other situationship, which would derail my openness for a committed, exclusive romantic partner. If you want a script, here’s a text I’ve sent:

“If you would consider a platonic friendship I would be up for {checking out a restaurant, etc, [based on whatever that particular guy and I had in common, note that I purposely give a specific suggestion of the kind of thing I’d be interested in]}.“ If they say they would be open to it, then before we make a plan I send a text that looks something like this (only the first time): “Sure, I’d love to. Not to be presumptuous and with apologies if this is unnecessary, since we’re just going to be platonic friends I am still actively out dating, etc. If we’re on the same page then sure, I’d love to check out ___ on Friday.”]

Dear Tricia:

No, no, no, no. I hadn’t had sex with them. Although to be honest there is one in particular that I would have really (really) wanted to (he turned me down, which can dull an urge pretty effectively). I’m talking here about men who I’d had maybe one or two initial meetings with at that point, where we hadn’t had sex because, remember, the romantic feelings weren’t there for one or the other of us. That’s the reason we (collectively) are in this predicament; someone (at least one of us) didn’t have sexual feelings. This wouldn’t work for me with men who I’d had sex with. That’s a whole other thing. I don’t think there is anything wrong with mixing sex and friendship (just like I don’t think there’s anything wrong with sex on the first date) (conceptually or morally, in both cases), but it’s rife with the potential for misunderstanding or heartache or both, so it could ruin the friendship and you’d end up without that person in your life entirely. So you just have to assess the risk/reward there on a case-by-case basis.

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For Spring! Three Things I'm Crushing On: From CRUSH Reader Lydia*

Downy Wrinkle Releaser Spray. This is a miracle product. Don’t question it, just order it. Unless you like to iron (which, who does?). I wear a lot of linen and if you wear a lot of linen (and why wouldn’t you, with this product) then you’ll need this. You don’t have to iron - just spray and pull the fabric and the wrinkles relax instantly!

Mirth Bottoms/Pants. So comfortable and easy. As carefree as sweatpants, less ubiquitous than white jeans and just as stylish. I have them in white and oatmeal for summer! Black for fall!

Hourglass Ambient Lighting Palette.This is a MUST have. So natural. The perfect “no make-up/make-up.” It’s not cheap but it lasts forever.

Anything else you’d like to tell us?

I love all the recommendations from The Crush Letter - everything from what to read or watch, to how to let go of friends (The Friend Edit piece by Dish was sooooo helpful). Keep it coming.

Want to tell us what you're currently crushing on? We would love to share it. Let us know here!

Social Media I Loved This Week


Song of the Week

Fumbling Towards Ecstasy by Sarah McLachlan

Sarah McLachlan is going on tour. It is the 30th anniversary of the release of her Fumbling Towards Ecstasy album and she is going to play the album in full. For a certain woman of a certain age (I am one), scoring tickets to this is going to make for a very especially special, and especially ethereal, night. We’ll be possessed. Because your love is better than ice cream. Better than anything else that I’ve tried.

She’ll be joined by Feist.

Live from her 1999 concert film "Mirrorball"

Hope that you have a wonderful Easter if you celebrate it. Otherwise, just an altogether wonderful week end. Thanks for being here. I love you.

Dish Stanley XO,

Re-Reading Erotic Lit Classics: Reviews By Christian Pan
In this series Christian Pan re-discovers classic erotic literature from a current perspective. Re-Reading Erotic Lit Classics: Delta of Venus by Anais Nin. Reviewed By Christian Pan The French-Cuban-American writer Anais Nin is one of the more complicated literary figures from the previous century, especially in relation to her contributions
Hot Thots. By Dish Stanley
A periodic column where Dish lets off steam. It Takes Time (and Tennis?) To Really Know Somebody. Have you ever met somebody and felt, instantly, as if you knew them all your life? Right. Me too. Perhaps they remind you of somebody else you love. Or loved, and still long
Things I Overheard On My 17 Hour Flight from Auckland, NZ to New York City. By Dish Stanley
“I’m 64 and I’ve never been to New York. I’ve wanted to go my whole life! Can’t wait to try my first In-N-Out burger.” “Oh my god. What happened to Meg Ryan‘s face?” {Ryan’s latest rom com was an ‘in-flight entertainment’ offering} ”Honey. I

If you love me as much as I love you (and I really do love you!), then please help me grow by forwarding this {love} Letter to a friend! And I'd love to have you join us on instagram.

The Crush Letter
The Crush Letter is a weekly newsletter from Dish Stanley curating articles & intelligence on everything love & connection - friendship, romance, self-love, sex. If you’d like to take a look at some of our best stories go to Read Us. Want the Dish?


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