Who's the Boss?
by Dave

Man kissing woman's shoulder
Ok, so this one has nothing to do with bad 80's TV but it's still a lot of fun. Who's the Boss is about control - one of you having complete control of your date and the date. What does that mean? It means that one of you will be in charge of everything – where you go, what you eat, what you do, what your date wears, everything. Ok, now I know a few of you are thinking, "Ewww...is this one of those weird sex dates?" No, that's not the point. It's more about pampering someone you care about and giving them the opportunity to get exactly what they want for a night. Who hasn't dreamed of being king or queen and laying down the law? If the fun on this date seems a little one-sided, don't worry, you'll switch it up next time so that the other person has a chance to be the boss. Plus, when the evening's over your date will definitely want thank you for it! (in case you're wondering, never ever suggest this to someone who's not a boyfriend, girlfriend, or spouse, because you will come across as sooo creepy.)

This date is best when everyone gets into the spirit of their roles without taking things too seriously. Here are a few thoughts to help you get in character, and remember, don't get tweaked, it's only a game.

The Boss
I like to think of the boss as 'The man'. We all know 'The man', right? Rich, captain of industry, large and in-charge, and all that. Well, that's the boss. They don't ask for things and never raise their voice, orders are carried out because that's just the way it is. Before a date, the boss will let their companion know exactly how to dress, from clothes and hair down to little details like perfume or cologne, shoes, makeup, and even undergarments. They may also have a list of tasks to be completed before the date starts. For example, a late-night at the beach might require a blanket, wine, and a favorite dessert. The boss will expect these items to be ready before the date begins. Pulling off the role of the boss is all about attitude. When the boss is ready for another piece of chocolate, they don't ask for or demand it, but instead mention "I'll have more chocolate now" and wait for it to be served. It's good to be the boss.

The Bossee
Conditioned to do as they're told by years of working for the man, a bossee carries out orders without question or hesitation. If informed they'll be watching The Notebook that evening, a bossee knows better than to object or even wince, though the pain will certainly be great. Instead he may utter a "Very good" or even suck up to the boss a little by saying "Nice choice". While the movie plays the bossee will be happy to give the boss a foot massage and keep her glass filled, focusing on the boss' comfort. The bossee's job is to make sure things go smoothly for the boss.

So those are a just few directions to go with the characters, but the mood of the date is really up to you. Use your imagination and go for anything from being hand-fed grapes while the bossee fans you to blowing up the baby pool for a little Jell-O wrestling. Sit down ahead of time and kick around ideas about fun ways you'd like to approach the date, but ultimately it's up to the boss to come up with a good plan. The boss has the fun of getting their way all night so it's their job to make the date exciting for the bossee by keeping them on their toes. If you're the boss, don't share specifics ahead of time, let the date unfold as it goes and the bossee will enjoy it more. Remember, with all of that power comes responsibility. If the date's a dud, it's on you.

The most common way to handle this date is to let someone be the boss for an afternoon or evening. Sure you could do it for an entire day or switch the day up and each take half, but it may get a little old if you drag the theme out for too long.

The last, but possibly most important, point to talk about is ground rules, plenty of ground rules. Bosses can get carried away so you'll need to have a way of letting them know they're out of line without ruining the fun. The boss should also remember that this date is supposed to be enjoyable for both of you and pay attention to signs that the bossee is getting upset or annoyed and take a timeout to talk it over. After that, think about things like what behavior is allowed in public, off-limit clothing or activities, and issues concerning physical intimacy. Good communication ahead of time makes it a better date for everyone!

Ideas for Bossing

Dressing your Date

  • Clothing
  • Hair style
  • Make-up
  • Jewelry
  • Facial hair or other
  • Nails
  • Shoes
  • Cologne or perfume
  • Underwear or lingerie
  • Costumes?

Get Pampered
  • Receive a foot, full body, or hot stone massage
  • Let the bossee bathe you in a tub with salts, oils, or bubbles
  • Manicure or pedicure
  • Have them feed you grapes or chocolate by a fire
  • Plenty of candles and music
  • Jacuzzi

Physical Intimacy
  • This can be one of the best parts of the date, get creative!


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