Jessa-fy my relationship
December 29, 2013 5:44 AM   Subscribe

What fun, romantic, slightly edgy things could I do with my boyfriend? Things are really good between the two of us, and we are not particularly "edgy" people. He is extremely sweet and actually a bit of an introvert. But we often joke that deep down inside, he has a part of him that wants to be wild and carefree, and flirt with danger. We refer to this as his "inner Jessa" after the obnoxious character on the series Girls who lives for the thrills and doesn't care what people think. What surprises could I spring on him that will appeal to his inner Jessa? What have you done for your boyfriend/girlfriend along these lines? It should be something fun, unconventional and maybe slightly transgressing society's accepted boundaries.

Ideas I had so far:
1. Wake him up at 7am, wrap him up warm, book a taxi and take him to this multi-storey carpark with an amazing view from the top, and watch the sun rise over the city with a hot drink. We will have to charm the security guard into letting us go up there but I think it's doable (and that totally adds to the Jessa-ness).
2. Dress the two of us up smart and go to a fancy reception where we don't know anyone, get drunk off the free wine, convince people that we are important diplomats, cause some mild trouble.

Note: I do realise it's kind of lame to plan this kind of faux-spontaneous fun, but I don't know, this is something he has hinted he would enjoy. I'm not really up for anything that could actually get us in trouble or hurt anyone. We don't have cars, or much money to spend, but slightly splashing out (for example, the taxi to the car park) would still be very much in the Jessa spirit of things.
posted by creeky to Human Relations (18 answers total) 36 users marked this as a favorite
Check out some things from this Askme.
posted by EmpressCallipygos at 5:48 AM on December 29, 2013 [1 favorite]

This isn't helping your question, but for the love of little kittens DO NOT DO number 2. Weddings are enough of a costly nightmare without having to deal with gatecrashers trying to have a whimsical fun time at your wedding.
posted by nerdfish at 6:30 AM on December 29, 2013 [13 favorites]

Go white-water rafting.
posted by herox at 7:37 AM on December 29, 2013 [1 favorite]

Isn't this what outdoor sex is for?

Fwiw, I don't think #2 is referring to a wedding reception.
posted by gaspode at 7:42 AM on December 29, 2013 [13 favorites]

Urbex! Cheap and doesn't need to be hardcore to be exciting, just jumping over a fence in an abandoned lot to see what's there will give you a thrill.
posted by Tom-B at 7:44 AM on December 29, 2013 [1 favorite]

I think you should aim for 'real fun' like go rock-climbing together (take a class), or go bowling (maybe use fake french accents or something to be 'zany'). It's hard to set up a romantic comedy-type sitution. I think it's better to do something active with a tiny risk element that will make you both feel a little bit excited and more bonded. (I'm not saying anything else as I see previous comments were deleted!).
posted by bquarters at 7:45 AM on December 29, 2013 [3 favorites]

Dress up and go to some posh hotel bar separately, and meet each other as though you were strangers in some film noir. Make up fake names and histories, and possibly accents, for yourselves. Then go have hot sex in a hotel room (or a handy broom closet or back alley or wherever you like).
posted by orange swan at 7:51 AM on December 29, 2013 [8 favorites]

Round where I live there are lots of old decaying industrial areas which are fun to explore and sometimes even have walking trails. They are pretty good for the kind of exploring which is a bit off the beaten track but not really actually dangerous unless you want it to be.
posted by emilyw at 7:51 AM on December 29, 2013

Dress up and go to some posh hotel bar separately, and meet each other as though you were strangers in some film noir. Make up fake names and histories, and possibly accents, for yourselves. Then go have hot sex in a hotel room (or a handy broom closet or back alley or wherever you like).

Was going to suggest exactly this. Alternatively, you go rent a hotel room. Have the room key couriered to him at work with a note saying "12pm," (or whenever he has lunch). Be waiting in whatever state of (un)dress would get you both happiest. Dirty nooner ftw.

Then pull a Mad Men and stay until he's done work, fuck like bunnies all evening.

Road trip. Obviously. Pick a weekend, get in the car, and just go somewhere. My freakin' toaster has GPS now I think so it should be impossible to get lost. Don't pick a destination, just drive, and flip a coin or something when you hit intersections. See what happens.
posted by feckless fecal fear mongering at 8:09 AM on December 29, 2013 [3 favorites]

Check out the Wikipedia article for experimental travel, and follow some of the links. Contains ideas like:

"Alternating Travel - in which a tourist leaves their front door, turns right, turns left at the next intersection, turns right at the next, and so on, alternating each direction, until they are unable to continue because of an obstruction."

"Cecitourism - in which a tourist is blindfolded and allows a friend to escort them through the city."

"Erotourism - in which a couple travels separately to the same city and then tries to find each other."

You can do most of this stuff in your own town, no expensive travel required. Or you can go to the train station, pick a train to anywhere, and spend the day there.

(This might be more Kirsten Dunst in Elizabethtown than Jessa in Girls, but then, Jessa is kind of an asshole.)
posted by Mender at 8:14 AM on December 29, 2013 [14 favorites]

Rent a treehouse, or get private access to one for a day and a night; somewhere rural, not urban or suburban. Definitely away from the sounds of people e.g. cars, industry, voices; somewhere rural, the more isolated the better. Preferably one with an open roof i.e. not a boxed-in room, where you can see the sky, clouds, the stars and planets come out as dusk falls.

Take a picnic, plenty to drink, a few blankets and pillows, some candles, massage oils, sources of warmth for the evening and night. Leave all your Internet gizmos and devices behind (but paper and pencils for writing and drawing, the odd book or two, are fine). Now relax and have treehouse sex; totally indulge and lose yourselves in each other, give yourselves up to each other, several times. There is just you, your lover, and nature. Nothing else and no-one else matters for the time you are there.

I can assure you, once you have made love - with the right other person - to psithurism, with a big blue sky overhead that changes to a star-filled canopy as you enjoy each other, outdoor sex will become a major desire, a more intense aspiration, of your lives.
posted by Wordshore at 8:38 AM on December 29, 2013 [5 favorites]

Yeah, the easiest (and perhaps most fun) way to indulge this impulse in a guy is probably through small sexual adventures.

In the middle of a boring movie at a theater, whisper in his ear that you want to meet him in the unisex bathroom outside. Start something in the car while he's driving and see how he reacts. Go out to dinner and reveal to him in the middle of the appetizers that you aren't wearing underwear.

I may be getting a bit crude, haha, but if you do stuff like that 9/10 guys are gonna unleash their "inner Jessa", guaranteed.
posted by johnpoe50 at 9:25 AM on December 29, 2013

I still giggle about the time that my friend and I hopped a fence into an over-the-top decorated yard at Halloween so we could smoke a joint in a fake graveyard. This works right now since a lot of people still have Christmas decorations up...
posted by Juliet Banana at 9:29 AM on December 29, 2013 [2 favorites]

I have an old friend who is somewhat of a Jessa-type, though much less of an asshole. As far as I can tell, the main trick of her escapades seems to be going out and talking to strangers, which leads to meeting interesting people/hearing about events/invitations to parties, as well as being okay with mild trespassing. So you can try to plan something specific or you can just go out exploring and try various combinations of 1) talking to strangers 2) exploring places you probably shouldn't be, but wouldn't get in real trouble for. In high school these places might be abandoned buildings, constructions sites, cool views technically on people's property, skinny dipping in public lakes. After college it became going to parties without invitations ("See those people there, let's check it out"), using roof decks/swimming pools in hotels without being a guest, befriending wealthy people for experiences, etc. As a more anxious person, doing these things were alternatively exciting/scary, but it certainly stretched me to see that mild breaking of societal rules/adventuring tends to have very little consequences. I may have run away from a few places, but I never got into any real trouble. If either of you have a friend like this, it might be better to accompany him/her somewhere and so to get some of this energy/style vicariously? Otherwise I do like the idea of creating characters for yourselves that do this stuff, where mild mannered creeky and boyfriend might not.
posted by amileighs at 9:38 AM on December 29, 2013 [2 favorites]

If you can get past the Insane Clown Posse association and ignore the many quests that will get you beaten up or arrested, the role playing game Morton's List would be perfect, I think.
posted by Juliet Banana at 10:49 AM on December 29, 2013 [2 favorites]

Pool-hopping! Climb fences, dart through bushes, tiptoe into backyards and outdoor community centers, and slip in to the water on a hot summer night. Bonus points for skinny-dipping, of course.
posted by thinkpiece at 12:05 PM on December 29, 2013

Go to a strip club together. Do some research online to find out which ones are nicer establishments and couple-friendly. Sit up at the stage and tip generously, both of you. Get a couples lap dance while you're there. Make sure to bring lots of 1s, 10s and 20s for tipping and buying dances. Dress cute and wear sexy underwear. Check into a motel on the way home and have sex. (Or don't... I think we actually stopped at a Denny's for pie on the way home.)

Go to a BDSM club. Dress to fit in. Soak up the atmosphere, maybe do a little public fooling around (make sure to follow the rules of what activities are permitted.) Chat with some folks. Enjoy the sort of people-watching you don't see every day (respectfully, of course.) Bring a few mild toys to try out. Maybe a rubber whip or a thin paddle. Check out the playroom, if there is one. Let him tie you up and whip your tits. Or tie him up and whip his tits. What happens at the club, stays at the club.

Our local dungeon hosted an open party on Halloween a few years ago, so we dressed up and went. It was great fun, we met some interesting people, saw some things we can't unsee (and I honestly feel like I can say I've now seen EVERYTHING thanks to that night.) It was fascinating and fun and felt like a great adventure for a mostly-vanilla couple from the 'burbs.
posted by Serene Empress Dork at 5:26 PM on December 29, 2013 [1 favorite]

Response by poster: Thanks so much for all the ideas! Some of these are great - looking into Urbex, this would definitely work. Treehouse idea is great. The more role-play-related ones could also be really fun.

And yes, to clarify, of course I wouldn't dream of going to someone's wedding reception - I meant corporate-type drinks receptions. Although I'm sure the real Jessa wouldn't hesitate.
posted by creeky at 4:00 AM on December 30, 2013 [1 favorite]

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