Musings + Essays
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10 Things I Love That I Shouldn’t.*

By: Jen Shoop

This week, I came across this old post from 2018 (…!) and almost didn’t recognize myself in it. I mean — I still love some of these things, but not all of them, and I try to avoid the word “should” as much as I can nowadays. I would never title a post this way in 2025. (What good has “should” ever done? It’s a guilt-inducer, a shame-chute. And nothing grinds my gears more than someone telling me: “you should have done x”!) But the past is a foreign land; they do things differently there. And 2018 was pre-Bethesda, pre-COVID, pre-Hill, pre-second-apartment-in-NYC, pre-coming-into-my-own-at-40. So much has changed. One of Landon’s mentors talks frequently about how things tend to happen in clusters of four year periods, which she calls epochs, and I find the concept interesting. I often contemplate where I might be within an epoch. Am I at the start of a new one with the book deal? Am I in the middle of things with the blog in full swing? I don’t know, but I can say that this post was over an epoch ago, and it reads that way.

But, we are in constant re-writing. And we are always raising future versions of ourselves. I am confident that Jen at 50 will have an entirely different tack. This reminds me of a time in college when an old friend told me: “You’ve changed so much,” and it had the slightest underbelly of insult. I didn’t know how to respond then, but all these years later, I wish I could go back and say: “Isn’t that the point?” It’s a beautiful thing, to realize you’ve changed for the better.

Anyhow, if I were writing a list along the same lines of my 2018 one, here’s how it might run:

10 Weird but Harmless Things I Love

+Eating the best bite of something first. (My husband is the opposite! He will literally eat his way around a sandwich so that the last bite is the best.)

+Going to bed with wet hair. (Still a favorite “bad girl behavior.” I pay for it in the morning but damn does it feel good.)

+Bird-watching — I can’t not comment on a bird. God forbid one lands on a branch outside my studio. The funny thing is: I don’t even know much about birds. I would consider myself a pre-amateur bird enthusiast. Usually when I’m into something, I’m all in, but this is just a situation of fuzzy wonderment. Funny enough, when I went to find a photo for the top of this (edited) post, I searched for “birds” in my Apple photos library, and I took this one in 2013, when I lived in Chicago and took much fewer photographs of my life. Not much has changed, I suppose. Once a bird enthusiast, always a bird enthusiast.

+Drinking iced lattes all year round. (My sister has described this behavior as unacceptable.)

+Needing to use a word the week I learn it. I collect words in my journals, and sometimes write exciting new discoveries on individual post-it notes on my desk. I am literally vibrating with energy until I find a way to work the newcomers into an essay.

+Reading my Kindle in bed with the lights out. Why the lights out, I don’t know — I could easily have the light on and a better reading experience. But it feels one step closer to sleep, one bridge closer to comfort.

+Room temperature foods. I mean, of course I like the things that are meant to be hot hot (i.e., soups), but I have no prohibitions against room temperature foods. Grilled asparagus? Fried chicken? Charcuterie? A pasta salad? Love all of these things at room temp.

+Eating cherries and savoring the pits for a long time. This one is, admittedly, very weird.

+Wearing socks to bed. I know there are sock-in-bed haters out there, but my feet are always freezing!

+Deferring substantive conversations until I’m sitting. Landon really got me on board with this one. Sometimes we’ll be flitting around the kitchen, and we’ll start talking about something more substantive, and one or the other of us will say: “Wait! Let’s sit and talk.” I find it much easier to really focus and think carefully this way. It also makes the conversation “the thing.” I’m not shoe-horning it into my day, around chores and errands. I’m sitting and making the conversation the main course.

Now your turn — what weird but harmless things do you love?

******

My original (2018) version of the list:

10 Things I Love But Shouldn’t (2018 Edition)

+Going to bed with wet hair.

+Buying toiletries in bulk ostensibly to appear to be a prepared adult but principally in order to line them up in neat rows in the cabinet. 

+Falling asleep with the TV on.

+”Accidentally” eating the fatty bits of pork or steak.

+Long showers.

+Bad chick lit.

+Cheetohs.

+When plans fall through.

+Apple juice (“but it’s just sugar!”).

+Any and all fruit candy — including and especially Now&Laters, aka cavity-inducing, tooth-cap-removing industrial runoff.

What are your guilty pleasures?

*”If everyone is thinking alike, someone isn’t thinking.” — Patton

Shopping Break.

+Love this popover dress and eyelet shirt at J. Crew.

+Wow – the print on this chic top. (Also available in shorts.)

+OMG! Splendid is offering an extra 60% off their sale section here. Lots of great buys, but do not miss this $52 cardigan (orig $188). Love it in the cactus color. And I hate to be the devil on your shoulder, but this white gauze set is next level in terms of fit and comfort. Get it in the white! Layer the pants over swimwear, with tanks, etc — or wear as a set for summer travel days, lounge before bed, etc!

+If you like the look of my raffia Freda Salvador flats, you might like this similar pair for $130!

+Speaking of raffia…I’m in love with this Loewe clutch. It is SO GOOD. I can’t unsee it. Out of my budget for what it is but…someone please buy.

+Another fun statement necklace for summer – this one from Tuckernuck. Love the fish beads! (Similar picks here.)

+Speaking of bold jewelry, I’m in the market for a big cuff. Love this one from Lizzie Fortunato in either tortoise or lilac.

+This overnight tote is so charming!

+A good ($15) look for less for my Varley shorts.

+Other things I’m loving at Target: this striped dress, this nap-dress-coded patterned mini, this striped terry polo.

+Nano-trend I’ve been noticing: denim jackets with military-inspired details, like this Nili Lotan.

+Excuse me, but Tod’s handbags are so chic…! I love this, this, this!

+Love all the bold patterns and colors from Cala de la Cruz!

+Amazing pareo – under $100.

This post may contain affiliate links. If you make a purchase through the links above, I may receive compensation.





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Anne
Anne
15 hours ago

It’s always hilarious to me how many Chicagoans drink iced coffee year-round. I’ve noticed this in a friend of mine too who lived there.

When I’m reading on my Kindle, nothing is better than reading with the lights out and then rolling over in bed and falling asleep with the Kindle in bed. Why I won’t extend the arm out and put it on the nightstand I don’t know, but there’s something satisfying about it.

MK
MK
6 years ago

Guilty pleasures! Oooh, my biggest one is definitely Instagram [insert teeth-gritting emoji here]. The Screen Time monitor on iOS has been a total game-changer, though! And I have to say, I’m with you on the necessary interludes of bad chick lit in between more substantive fare.

Re: pajamas, I have heard great things about Lake and may try them out this holiday season. I tend to just sleep in (un-matching) soft cotton t-shirts (loved the garment-dyed options that J.Crew have had in the past) and thin sweats (favorites are a black cupro pair of joggers from Anthropologie and tapered cotton sweats from Muji). I’ve also been intrigued by the Lunya sets and will let you know if I try them!

I Love Mr. Mittens = so tempting!

trackback

[…] week Jen had a really fun post up about her guilty pleasures… things she loves but shouldn’t. I loved the post so much – and there were a lot […]

Rachel Kravitz
Rachel Kravitz
6 years ago

I dont think we should feel guilty about any of our pleasures. I wanted to share an article I wrote about it this summer. (not plugging any blogs or anything, Ive written 2 articles….)
http://www.jewishwomentalk.com/2018/06/26/on-guilty-pleasures/

Rachel Kravitz
Rachel Kravitz
6 years ago

So I wrote an article this summer about not criticizing our entertainment choices. Since you put “bad chick lit” on your list, I felt compelled to share http://www.jewishwomentalk.com/2018/06/26/on-guilty-pleasures/

trackback
6 years ago

[…] 7. Debating creating my own “guilty pleasure list.” […]

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[…] this guilty pleasure list. Maybe I’ll write […]

Stephanie
Stephanie
6 years ago

I love eating the “extra” frosting whenever I bake a cake.

Cait
Cait
6 years ago

I ordered some Rothys and absolutely love the look, feel, comfort, etc, and love that they’re vegan. I have had a big problem with them retaining odor though- even after washing in the machine according to instructions. It’s now at the stage (only 3 months after getting them) that I feel like I need to wash them after every wear- and this is not a problem I’ve had with other shoes, including other vegan & washable shoes. It was such a shame- the first few weeks in, I was all ready to buy out the whole range!

Cynthia
Cynthia
6 years ago

I’ve also heard great things about Rothys. I’m thinking of getting a pair to switch into as the night lingers under a long gown dressy wedding. I’m loving the grey zebra and the camo -not for the wedding, but everyday!
I love the fur sleeves on the jacket but here’s my problem…you wear it once and everyone likes it. You wear it again and everyone says, “oh, I’ve seen her in that before”. Better to stick with a stable Glen plaid you can wear again and again and not be remembered for the wrong reason!
Xxoo

Hannah
Hannah
6 years ago

if you’re looking to try a new brow crayons, after much trial-and-error, I’ve committed to the Anastasia products! for natural lines, the Brow Wiz pencil is fantastic, and for a deeper fill, the Brow Definer is awesome. I am also a convert to their brow gel – holds up super well with no residue.

Sarah
Sarah
6 years ago

I love the $1 Elf clear mascara for my eyebrows. You’ll never go back!

Betsie
Betsie
6 years ago

I own the knit your love cardigan in bubblegum pink and as cute and cozy as it is, the yarn sadly didn’t hold up. After only one wear, it looked old. Just thought I’d share. So in this instance the splurge may be worth it.

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