Five Date Ideas

More date ideas coming to my free Substack – On Sex & Donuts – beginning May, 2024!


Here are five a few of my more unique ideas! I originally posted this in 2023 plus two new dates finally added on 2.5.24!

This list provides you with some excellent insights and reading it will give you a sense of what I enjoy and inspire you to incept an adventure of your own. If you come up with an idea and are uncertain as to whether or not I’ll be game, feel free to send a PG rated email and inquire prior to screening & booking. 🥰

DREAMY (added 2.5.24) An example of a dreamy date can be found in a recent multi-day holiday experience with a new lover. He knew he’d be in Chicago for a finite time in December of 2023, was positive we’d get along swimmingly, and booked me for not one but two extended dates. An impassioned overnight, multiple sprawling suites, and an intimate dinner for two in an urban cabin.

Thought provoking conversation, scores of kinky toys he shipped to me ahead of time, and the Bordelle pictured below. It was a dream, and a well researched one a that. With every interaction, this man made it clear that he’d scoured every page of my site and blog. And when we met, he cited these 2 posts as being particularly informative:

Click to read about things I like.

Click to read about the types of men to whom I’m wildly attracted.


HANDHELD (added 2.5.24) We down a few wagyu hand rolls – or go deliciously wild and trust the chef – at Yokocho. At some point, I’ll tell you to check out the sexy red bathroom. (No, really.) Then after you do, we’ll talk about how we’d love to make out in there someday before heading to Emporium for some hot arcade action. You’ll kiss me before we go in to get our nostalgic fix. Then, later, we’ll hold hands and walk back to our suite at Nobu. (Notice I don’t suggest we actually dine at Nobu. Subpar doesn’t suit us.)


DRAMATIC Dinner at Sepia or Beatnik on the River before walking over to The Lyric to catch a show.


CIRCUITOUS We dress to the nines, meet a beloved dive, and ask our bartender to determine our dinner spot. Then at dinner, we ask our server where we should land for a nightcap / non-alcoholic night cap. No vetoing. We will commit ourselves to embracing the night with chance as our guide. Bonus points for doing this in your favorite domestic city or somewhere abroad.


SERENE Hiking, camping, lovin’ on each other and decompressing. This is a fabulous list of destinations. 


PAMPERED We book a suite at The JW Marriott, lavish ourselves with one of their extraordinary couples massages, then eat our fill of room service (and one another) before taking a nap.


ELEVATED Paragliding in Belize. Don’t worry, I’m not afraid of heights, and I own enough sunscreen to protect an entire desert island full of Irishmen. (View photos from a February 2023 bikini-clad FMTY are posted below.)


HILARIOUS As you’ve already ascertained via my gallery, I’m a huge fan of standup comedy. Is this something we have in common? Let’s go see one of our favorite comedians live and ugly laugh til we cry. (In 2021, a member of my inner sanctum flew me to Baltimore to see Last Podcast on the Left live and crash with him at The Four Seasons for a few days. ‘Twas a riotously funny and erotic dream.)


GREEN We stroll hand in hand through the botanical gardens as you tell me about your green thumb and I confess my that mine is black. Then back to the boudoir we go for something more salacious ahead of a couple of Fill Colinses at Aviary (make mine non-alcoholic, please) and dinner at Bloom Plant Based Kitchen.


BRUTAL We satiate my love of Brutalist architecture by setting out upon a tour of our city’s most iconic concrete monoliths, and we nibble and sip at assorted establishments along the way.


ADORED We grab some Pho at Sunda, Le Colonial or Pho 777 or before a day of luxury shopping. You indulge our mutual high heel and pretty dress fetish and I buy you something small, wife-proof, carryon ready and discreetly meaningful to commemorate our day together.


TRIUMPHANT We grab a couple of dogs at The Weiners Circle and plot our Florida getaway After all, you do have meetings in Tampa and I am overdue for a return visit to the near-ish by Dali Museum. 🙂


NERDY They really ought to hurry up and release the Venture Brothers movie because boy howdy do I have the best nerd date idea! We watch it while lounging naked in bed & eating a variety of Venture Brothers themed foods: vegan spring rolls, a block of Asiago cheese, grilled cheese sandwiches, tortilla chips & ranch, etc.

Unfamiliar with Venture Brothers? Let’s build a themed date around a nerdy movie or TV show we both love. 🙂


ATHLETIC We lift together in a well appointed hotel gym (I’ve kept a nationwide list!) and I teach you the importance of farmer carries. You, in turn, chide me for my disdain of the steady state cardio. (I do it every day and I loathe it every day.)