Middles & Teen Regressors Module, Part 9: 20 Dates for You and Your Middle

Good Afternoon Friends,

We’re back with another section in this “Middles and Teen Regressors” series. I hope you all have been enjoying it. I was curled up the other night pondering dating. When you’re in a D/s relationship, dating can take many forms. If you have an adult baby, perhaps you take them to a trampoline park, or to ride on a carousel. Littles would enjoy being pushed on the swing at the local playground, or to take in a matinee movie at the local cinema. But what about Middles? What would they like to do for dates? I compiled 20 dates that are perfect for you and your middle to enjoy. Whether you identify as a Middle, or you slip into middle space every now and then, this list will surely have a date for everyone to enjoy. Are you ready to get started? Then, let’s dive in. ❀

20 Dates for Dominants and Their Middles to Enjoy:Β 

  1. Roller Skating: Never underestimate this inexpensive date. While roller skating may seem to be “out of style”, this iconic date will have you and your middle giggling as you wobble around the rink together. Experience not required. πŸ˜‰
  2. Drive-in Movie Theater: I’ll let you in on a little secret. If you ever want to go see a movie, check out a drive-in movie theater first. Why? Because they are cheaper and you can bring your own food! Pack a picnic dinner and off you go!
  3. U-Pick Farms: If you find a local farm that offers u-pick times, seize the day, my friends. Whether it’s apples in the fall, strawberries in the summer, or blueberries in the spring, there is always something to pick and turn into a delicious treat with your little one.
  4. Coupling Outfits: This trend actually began in South Korea. Couples wear matching outfits to symbolize that they are taken to one another. You can actually get quite trendy with it! Google it for yourself! πŸ˜‰
  5. Amusement Park: Your middle will squeal and grin as you take them on roller coasters, bumper cars, and Ferris wheels. Win them a plushie and eat a fried funnel cake together at your local amusement park.
  6. Cooking Together: This is probably my favorite type of date…. hands down. Cooking with your partner is so sensual, fun, and the food always comes out better. Turn on some tunes, grab a glass of your favorite beverage, and you’re ready to go.
  7. Mani/Pedi’s: Never let people tell you that a man shouldn’t get a mani/pedi because that is totally bollocks! Spoil your middle with getting their nails and toes done, while you get your nails freshened up, massaged, and filed. You both will feel like a million bucks afterwards.
  8. Spa Date: This is an amazing date that I’ve personally experienced in Middle Space. Grab your middle and head to your local spa. You can even sneak in some discreet touchy-touchy time in a private hot-tub. πŸ˜‰ Trust me.
  9. Go See a Play: Take your middle and go see a local theater performance! While the cinema is nice, seeing a play live or a musical, can be loads of fun. If a play isn’t your thing, see what other performers are coming to your local performing arts center.
  10. Window Shop at the Mall: This date is sure to put your middle in the head-space and it’s totally FREE too! (Assuming you don’t buy anything, and we all know that passing that dipp’in dots cart is nearly impossible! But I digress lol).
  11. Go for a Drive (and Let Your Middle Drive!): Let your Middle take a walk down memory lane as they be the one to drive you around! Crank up the tunes, put a fuzzy steering wheel cover on your car… and go! πŸ˜‰
  12. Wash the Car Together: Spray each other with the hose. Get soapy and wet as you do a mundane task like washing your car. Bring your Middle outside and let loose with your fun energy. No doubt you two will be laughing in no time.
  13. Attend a Concert: There are so many fun concerts to attend with your Middle. Let them choose which band or artist to go see. Then make a night out of it. (Don’t forget to pick up a souvenir!).
  14. Swimming: Splashing around in the pool with your Middle is a great way to beat the heat, while smushing close as a D/s couple. Lay side by side tanning, and then take a cool dip together as you splash around.
  15. Be a Tourist in your Town: This is such a fun date activity to do with your sub! Pretend that you’re a tourist in your own town for one day. Pick out a restaurant you’ve never been to. Visit an attraction or museum you’ve never seen. Take the day to explore your own town in a way you’ve never discovered before.
  16. Game Together: I love video games. And your Middle will get an absolute thrill out of gaming with you too. There are apps galore that are perfect for Middles. I also recommend hopping on Steam to find cheap and/or free games to play on the PC.
  17. Take a Dance Class Together: You don’t need to be experienced to take a fun dance class with your Middle. Salsa in your heels. Try a zumba fitness class! Whatever gets you moving and grooving… do it together. You’ll make priceless memories.
  18. Painting: Check out your local art studio and see what “Paint with Me” classes they have. Or, find a local pottery studio and recreate “Ghost” as you and your Middle cuddle and create a work of art together.
  19. Open mic night at a Coffee house: Relax to the sounds of local poets, writers, and the like as you snuggle up with coffee, tea, and cocoa.
  20. Take in a Baseball Game: I just had to tack this one on the list because being from The ATL (woot woot!) I can attest that a Braves’ game, (or any baseball game!) is soooo fun to attend, watch, and see. Chomp down on hotdogs and overpriced ice cream as you do the wave with the crowd. πŸ˜‰

Alright my friends, that’s it from me for this post. I hope you all enjoyed it. If you did, hit that like button and let me know. Smash that follow button if you’re new around here, to stay updated on the latest posts and I will see you back here for the next topic!

Much love,

~Kitten/Punkin Xx


  1. All great ideas, Punkin. Although, I must admit, mani/pedis are not my thing and matching outfits would interesting (to say the least). No matter how hard I try, I just can’t wrap my head around that one. Lol

    Liked by 1 person

      1. Ok. Those are definitely more tasteful than what I was imagining. Just don’t put me in a track suit, daddy don’t do track suits. The plaid was nice though. I can get behind that.

        Liked by 1 person

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