It's Christmas: give him the gift of naughty and nice.

December 12, 2008 5:48 AM

A dare: help a friend be naughty.

My friend J and his wife C are very, very close and have the type of marriage people envy: deep friendship, crazy good sex, infinite trust, beautiful children, and a bond for which an appropriate positive adjective fails me. In short, they are the best of friends. I am fortunate in that they share a great deal of their personal life with me.

Here's the dare: wife C is known for being extremely eagle-eyed and knows the most random minutiae of husband J's life, without even making an effort. They got the whole mindreading thing goin' on. They have made a bet with each other, the bet being that J in no way could ever do anything behind C's back without her knowing about it. In short, he has to do something clandestine and she has two weeks to identify what it is he's done.

So. J and I have been trying to concoct a plan for J to do something mildly naughty behind C's back to see if she'll figure it out. So far, we've only come up with semi-lame ideas like his sneaking to a stripclub during his lunch hour. ::yawn:: Given the, um, wide variety of wild in their sexual life, this is hardly sneaky or naughty enough to merit anything beyond a giggle from C.

For what it's worth, I'm pretty sure J's on the losing end of this bet. But I would like to give C a good run for her money. What kinda naughty, clandestine thing can J do to win this bet? Bear in mind I can serve as accomplice, the event can be - but doesn't have to be - sexually oriented (but that seems to be the direction our ideas are taking), and both J and C are extremely liberal souls who have infinite trust for each other. Any ideas?

posted by December to human relations (24 comments total)

Get him to make out with a guy.
posted by gadha at 5:58 AM on December 12, 2008

Do a George Castanza style underwear portrait. Mildly naughty (if you can call it that?) and will bring a lot of laughs to the table as well. Bonus points if you have have it done as a velvet painting.
posted by Mastercheddaar at 6:01 AM on December 12, 2008 [9 favorites]

Have him get a small, out-of-the-way tattoo. Ideally, behind his own back.
posted by Clyde Mnestra at 6:37 AM on December 12, 2008 [2 favorites]

Employ misdirection. Use one of your semi-lame ideas in conjunction with whatever real plan you settle on. Make it relatively easy for C to discover the semi-lame plan, so that when she does she thinks she has figured it out. For example, have a bunch of his friends go out to a strip club at some point and tell them all to drop hints to her that he went with them. But while they were at the strip club, he was getting that velvet painting done, or stealing a street sign, or whatever.
posted by googly at 6:39 AM on December 12, 2008 [4 favorites]

Take a cell phone picture of himself with his member in his hand in front of her parents' Christmas tree.
posted by headspace at 6:41 AM on December 12, 2008 [13 favorites]

This question is somewhat pointless without knowing any details about J because essentially you want J to do something out of character to win this bet.
posted by the_ancient_mariner at 6:47 AM on December 12, 2008

They must have family photos displayed around the house, right? How about photoshopping (or re-photographing) something naughty into it? I'm thinking a little visible nip, or replacing a snowman's nose with a dildo or something. Something that is not apparent at a glance, but would be impossible to miss if you actually looked at the picture.
posted by Rock Steady at 6:55 AM on December 12, 2008 [3 favorites]

Thanks, mariner. Here's J: early 40s, Army but not overly macho about it, highly intelligent, great sense of humor, attorney, very family oriented, faithful, liberal despite being military, frisky, blunt, athletic, and, admittedly, somewhat dorky with no game (his words).
posted by December at 6:59 AM on December 12, 2008 [1 favorite]

Something a little risque: You could set up a friend-affair. Get J to spend a significant amount of time over the two weeks with buddies; lunch hours, phone calls, text messages, emails, etc. Could be doing whatever; getting drunk at a bar, playing video games, etc, as long as it's not working and not hanging out with the wife. The take home point is that he *could* sustain an affair if he wanted to.
posted by craven_morhead at 7:06 AM on December 12, 2008

This is somewhat hard without knowing their routine/habits etc.

A picture of him in her underwear while she's sleeping the background.

How to get her underwear: from the fresh laundry pile (or some such) or straight from the dryer at some point.

For the photo: turn OFF the sound on the digital camera!
posted by Brandon Blatcher at 7:12 AM on December 12, 2008

He should buy a kit he can use to make a model of his own penis, make one, then check into a hotel one day and spend his lunch hour passionately making love to his own cloned genital organ.
posted by ShameSpiral at 7:23 AM on December 12, 2008 [2 favorites]

Have J start wearing C's panties. If he can go through her entire supply without her noticing, he wins.
posted by robocop is bleeding at 7:34 AM on December 12, 2008 [4 favorites]

J should do nothing out of the ordinary. Nothing at all. C will drive herself nuts trying to figure out what he's done, but she'll never find the evidence because there won't be any. In two weeks, when she finally admits her failure, J can inform her how he managed to deceive her so successfully, and he will win the bet.
posted by Faint of Butt at 8:17 AM on December 12, 2008 [12 favorites]

jeez, you guys are missing the point. what he needs to do is something to her behind her back, not himself. what he should do is plan some kind of adventure or getaway for her. lots of bonus points for things that require a lot of prep, like skiing/equipment or int'l travel/passport. maybe yoga class or something, too.

or, if it has to be him: have him do toastmasters and get her to come to the final speech he does. or maybe a martial arts class.

nthing the misdirection idea suggested by headspace.
posted by lester at 8:17 AM on December 12, 2008 [4 favorites]

Dye his pubes and he doesn't put out for 2 weeks.
posted by Ironmouth at 9:22 AM on December 12, 2008

Whatever you do, make sure you have one of his friends call the house when she's there leaving a message for him that the tests are back from the lab. And he should get in touch with them immediately. Just for misdirection.

I'm not totally sure what you mean by "naughty", though from your example it seems to be something a husband would traditionally get busted for. (But won't by his super understanding wife.)

If that's the case I suggest he takes out a craigslist personal and meets more than one respondent. (Meet, not "meet" or "meat") Make sure not to use his real name and make an email account just for that.
posted by Ookseer at 11:28 AM on December 12, 2008

Have him create a match.com profile and go on 1 date.
posted by 517 at 1:27 PM on December 12, 2008

Have him hire a masseuse to give him a massage in his own house.
posted by 517 at 1:30 PM on December 12, 2008

Ok, when you were describing their marriage and your relationship to it I had to doublecheck my friend hadn't gotten a metafilter account. And my husband's initial is J also, so it keeps throwing me. So I'm trying to put myself in C's position and think of what my husband could do behind my back that would really shock me and impress me.

Going on dates, definitely. I would have a hard time believing he was able to pull off actually meeting someone for a date. Professionally shot nude photos would also be a good one, but that depends on whether your friend is normally exhibitionist at all. Leaving the state to do something naughty and not raising suspicion. (Depending on how big your state is, I guess.) I also like the wearing her panties for the entire two weeks idea. Or alternately wearing some other outrageous article of lingerie for two weeks: pantyhose, garter belt and hose, bustier?

Anyway, if I have any more brainstorms I'll let you know.
posted by threeturtles at 2:18 PM on December 12, 2008

The thing about going on dates with others is that the others are expecting a real date. That isn't really fair to them.
posted by Ironmouth at 2:45 PM on December 12, 2008 [6 favorites]

Options that popped into my mind:

1- Nail the [of legal age of course] babysitter. That'll show C what she gets for upsetting the trust applecart.

2- Have him arrange a "date" with someone in his life that C trusts, and who is NOT an option for real dating. Like his brother or mother or boss or something. Go on the "date". See if C can figure it out.

3- Plan a surprise party for C. This is lame, but it's the least apt to cause marital trouble, and most apt to make C's day. If birthdays or anniversaries aren't nearby, make it a Christmas party.

If I were in J or C's position, I wouldn't like this idea one bit. This seems like the kind of thing that comes back to bite them. It just doesn't seem like proving that one partner could violate trust and not get caught, or proving that the other partner can't do *anything* without getting caught, is going to end well.
posted by gjc at 9:15 AM on December 13, 2008 [1 favorite]

I think the pantyhose idea is great. Although, the wife will probably be on the lookout, so if she notices all her pantyhose are suddenly missing, J loses. He should go out and buy several pairs for himself (Bonus: they'll fit better!) and wear them every other day or so. As long as he undresses himself those days and keeps his pantyhose separate (and hidden) C shouldn't be able to figure it out.
posted by Night_owl at 1:04 PM on December 13, 2008

Have him arrange a "date" with someone in his life that C trusts, and who is NOT an option for real dating.

I like this, but make it a series of "dates," phone calls, emails, etc.

Like his brother or mother or boss or something. Go on the "date". See if C can figure it out.

And for extra bonus points -- C's mother.
posted by Rock Steady at 6:47 AM on December 15, 2008

Take a sneaky voyeristic photo of C, have it turned into a really nice oil painting, sell the painting for a lot of money, and then use the money to for a surprise weekend vacation. Optionally, have more than one painting so as to increase the chances of selling one, and so that she will have a keepsake to remember the time she challenged her eagle-eye :)
posted by nnevvinn at 10:59 PM on December 22, 2008