How to Role-Play in Bed Without Feeling Like a Clown
Illustration: Olivia Fields

How to Role-Play in Bed Without Feeling Like a Clown

Just play your part and watch the magic happen

Every week that I write Dear Level, I usually ask my fiancé his thoughts. My partner is super open and has very few hang-ups about anything; if I want to talk about anything involving sex, he’s always game.

Until now.

Today’s topic, ladies and gentlemen, is role-play! Going all out. Getting into character — and sometimes costume — and putting on a performance worthy of a Pornhub Award. (Yes, there are really Pornhub Awards; no, you don’t want to be a judge.)

Feeling randy and have a little time to get creative? Boom. Grab one of your scenarios. Your partner will know something’s coming. But they won’t know what exactly.

In an episode of the sitcom The Good Place, after Eleanor reveals that she has a fantasy of being with a letter carrier, her partner, Chidi, indulges her by showing up in a postal uniform. Hat, shorts, the whole nine. The scenario was played up for laughs — well, kinda — but it made me wonder: How many of us are fantasizing about the letter carrier, the high school cheerleader, the ride-share driver? As usual, my research began with my pre-husband.

Me: Have you ever had a woman dress up for you?

Partner: Yes.

Me: Did you like it?

Partner: It was cool.

Me: Where do you stand on dress-up role-play? Is that something you’d add to our life?

Partner: I mean, maybe? I don’t know. It’s not something I’m personally seeking.

Me: So, it’s something that just needs to happen out of the clear blue sky?

Partner: Or not. It can be planned out, too.

Me: Come on, I need more words!

Partner: You need better questions.

Great talk. Thanks.

As a plan B, I reached out to friends for more insight. And for this week’s Dear Level, I’m sharing what I learned about y’all this week! (Well, most of you.)

  • Even if it’s not their thing, some dudes are down to role-play just to make a partner happy. “My wife has asked me to be more aggressive,” says a late-forties film director. “Like, a lot more aggressive. It’s not really my thing, but I know she likes it so I go with it.”
  • I’ve learned that some of you don’t mind “silly” role-play and fantasy. “My girl asked me to put on her thong once,” says a thirtysomething student. “It was more ridiculous than anything else, but somehow it was fun.”
  • Gender-bending is definitely a thing. More than one guy told me about switching roles. “It started with me wearing a dress as part of a Halloween costume,” says a late-forties teacher. “But after the party, I left the dress on. I’m super masculine so I think my girlfriend liked the dynamic of seeing me so different. It was cool.”
  • Role-play isn’t always about putting on a character; it can be super subtle. “My girlfriend and I often do the do-I-know-you? We meet somewhere and pretend we’ve never met,” says a thirtysomething attorney. “When the people at the bar see how we’re interacting — as strangers — it’s a turn-on.”
  • Some of you are a little worried about some fantasies when they stray into more taboo areas. “My wife has straight-up control and ‘ravishing’ fantasies. I can’t quite go there,” says one person. “It makes me super uncomfortable.”
  • Most men’s dress-up fantasies hew to the classics. When I asked how they’d want their partners to dress up, I got: cheerleader, tennis player, maid, attorney, judge(!!). And one lone request for a veterinarian. Oddly specific, and I have no idea what that costume would be, but no judgment!

The key to role-play? Go ahead, guess. (Hint: I riff about it every week.) That’s right: communication. If you’re into the idea, share it with your partner. For many people, requests from a partner are special in and of themselves. It feels good to make your partner feel good.

Once you’re both on board, come up with several role-play scenarios you’d both be interested in. Write them on small bits of paper, add them to a box or a jar, shake it up, and store it somewhere. Feeling randy and have a little time to get creative? Boom. Grab one of your scenarios. Your partner will know something’s coming. But they won’t know what exactly. So then there’s still surprise although we know everyone’s on board. Hope you’re ready for some improv!

So, I took this conversation back to my beau. I’m thinking maybe I should follow my own advice for once. It’s worth a shot.

Me: Alright, I’m done with my story. Do you have any fantasies?

Partner: Not any I’m telling you while you’re working on Dear Level.

There you have it. Keep it private. Keep it fun. I’m off to see if I can get my hands on a plumber’s uniform.