Picture the two of you alone together: Friday to Sunday, mostly naked most of the time. A dirty weekend should be two solid days of fun, sweaty, naughty, delicious isolation. Your girlfriend is onboard for the good time. Also, she wants to be romanced, indulged, and to walk into work Monday six inches off the ground sporting a glow her co-workers can’t quite place.
With more than my share of raunchy retreats, I’ve learned one true thing: You can’t have memories unless you make them—and a really wild weekend is a good time to do it. Here’s how:
How to have a dirty weekend getaway with your girlfriend
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1 OF 10
1 of 10
Define your terms
A dirty weekend can happen at home but shouldn’t. Ditch your routine and visit some other city, splurge on a fancy hotel, check into a budget motel, or pitch a tent in the woods. The only rule: no double dipping. It cannot be coterminous with any other activity.I had an ex who brought me along as his guest to lectures, college reunions, weddings, and the Big Game. It was never dirty. Those were just trips together. He married someone else.
2 of 10
Do your research
One woman’s “dirty” is another girlfriend’s “creepy.” We all have notions of what constitutes an erotic adventure, so get some intel about her tastes, preferences, and titillations ahead of time. My most recent rendezvous—a college friend, a boutique hotel—started weeks before, with flirty texts subtly sounding out the ground rules. He found my boundaries and cranked up the heat.So ask: What drives her wild? Then deliver.
3 of 10
Make a plan
A girl’s least favorite sentence is “I dunno, what do you want to do?” I will always be thankful to the ex who perfected this recipe, in which the guy: 1) Chooses the hotel and the restaurant. 2) Offers two options for an activity—sunset sail or concert tickets? Wine tasting or World of Warcraft?—so she feels consulted; and 3) Should she suggest a third thing, is willing to throw his entire plan away and do whatever that thing is.Treat the plan like your puppy: If you don’t pay attention and feed that sucker, it will die.
4 of 10
Consider backups
Planes get missed, picnics rained out, hot tubs stew up weird bacteria. An actor I briefly dated got shy in the sheets and our bawdy holiday morphed into a monologue of Maoist self-reproach. What he didn’t know: He could’ve rescued the night with a little creative thinking—say, paying more attention to me.So game out a Plan B in case of emergency—not just because it’s good to have one, but because having one tamps down the angst of delivering on a dirty weekend.
5 of 10
Bring equipment
Like the good scout you are, be prepared. To the obvious supplies of birth control and lube, add a selection of thoughtful gifts. For this dating columnist: champagne, dark chocolate, roses. But I’m easy. For a more imaginative woman, try hedonistic toys from your favorite adult shop or go for provocative outfits (lacy lingerie, sexy nurse, Pikachu).
6 of 10
Drop out
This is an order: Put down your phone. Avoid work e-mails. Log off Skype, Slack, and WhatsApp. Leave all your screens at home. As I learned on a recent weekend on Lanai, the hottest gift you can give is time away from anything that breeds anxiety.Hotels, by nature, help: Towels pick themselves up off the floor, room service delivers breakfast, stained sheets get magically replaced, and rude noises are only heard by strangers.
7 of 10
Stay on target
Naughty weekends are meaningless. I once brought a boy to a BBQ competition, and when we weren’t out eating, we were otherwise occupied. We didn’t have time for profound talks about life goals, where the relationship was heading, or, heaven forfend, marriage proposals. We were busy.You really have only one job.
8 of 10
Pick your moments
Breakfast and bedtime are easy opportunities for keepsake flashbacks. I flew 10,000 miles to a dirty week in Papua New Guinea, and while I’ll forever consider our escapade under a full moon at high tide an all-time erotic apex, I was equally charmed by the sweet details and jewel-like tableaus that seem like rituals in retrospect: He made me breakfast every morning. Every night before bed, we’d wind down with a G&T or a bowl of weed.Any ritual built on two nights is a layup.
9 of 10
Keep the peace
Don’t fight, obviously. But if you do, give in. You can talk about it later if you must, but for the weekend, simply capitulate: She’s right. You’re wrong.Don’t do what one guy I was with did and spend an entire weekend arguing about smuggling contraband kosher brisket into Turks and Caicos.Just suck it up and forget about it. Please.
10 of 10
Remember: it’s not about you
Improper assignations work best when you make her feel attended to, cherished, and spoiled. (My favorite pampered weekend: an oyster dinner in suburban Connecticut, an unremarkable hotel, and unforgettable sex; lather, rinse, repeat.)And here’s the special sauce: If you take care of her, she’ll take care of you back. That’s the beautiful circle jerk of love. Once you make it all about her, it’s really all about you.A dirty weekend is easy if you keep the stakes low: It exists for sex, nothing more, nothing less. That being said, do it right and the goodwill it spawns can last for weeks, even years.You both deserve a two-day horizontal timeout right now.So go have one, all dirty weekend long.
A dirty weekend can happen at home but shouldn’t. Ditch your routine and visit some other city, splurge on a fancy hotel, check into a budget motel, or pitch a tent in the woods. The only rule: no double dipping. It cannot be coterminous with any other activity.
I had an ex who brought me along as his guest to lectures, college reunions, weddings, and the Big Game. It was never dirty. Those were just trips together. He married someone else.
Do your research
One woman’s “dirty” is another girlfriend’s “creepy.” We all have notions of what constitutes an erotic adventure, so get some intel about her tastes, preferences, and titillations ahead of time. My most recent rendezvous—a college friend, a boutique hotel—started weeks before, with flirty texts subtly sounding out the ground rules. He found my boundaries and cranked up the heat.
So ask: What drives her wild? Then deliver.
Make a plan
A girl’s least favorite sentence is “I dunno, what do you want to do?” I will always be thankful to the ex who perfected this recipe, in which the guy: 1) Chooses the hotel and the restaurant. 2) Offers two options for an activity—sunset sail or concert tickets? Wine tasting or World of Warcraft?—so she feels consulted; and 3) Should she suggest a third thing, is willing to throw his entire plan away and do whatever that thing is.
Treat the plan like your puppy: If you don’t pay attention and feed that sucker, it will die.
Consider backups
Planes get missed, picnics rained out, hot tubs stew up weird bacteria. An actor I briefly dated got shy in the sheets and our bawdy holiday morphed into a monologue of Maoist self-reproach. What he didn’t know: He could’ve rescued the night with a little creative thinking—say, paying more attention to me.
So game out a Plan B in case of emergency—not just because it’s good to have one, but because having one tamps down the angst of delivering on a dirty weekend.
Bring equipment
Like the good scout you are, be prepared. To the obvious supplies of birth control and lube, add a selection of thoughtful gifts. For this dating columnist: champagne, dark chocolate, roses. But I’m easy. For a more imaginative woman, try hedonistic toys from your favorite adult shop or go for provocative outfits (lacy lingerie, sexy nurse, Pikachu).
Drop out
This is an order: Put down your phone. Avoid work e-mails. Log off Skype, Slack, and WhatsApp. Leave all your screens at home. As I learned on a recent weekend on Lanai, the hottest gift you can give is time away from anything that breeds anxiety.
Hotels, by nature, help: Towels pick themselves up off the floor, room service delivers breakfast, stained sheets get magically replaced, and rude noises are only heard by strangers.
Stay on target
Naughty weekends are meaningless. I once brought a boy to a BBQ competition, and when we weren’t out eating, we were otherwise occupied. We didn’t have time for profound talks about life goals, where the relationship was heading, or, heaven forfend, marriage proposals. We were busy.
You really have only one job.
Pick your moments
Breakfast and bedtime are easy opportunities for keepsake flashbacks. I flew 10,000 miles to a dirty week in Papua New Guinea, and while I’ll forever consider our escapade under a full moon at high tide an all-time erotic apex, I was equally charmed by the sweet details and jewel-like tableaus that seem like rituals in retrospect: He made me breakfast every morning. Every night before bed, we’d wind down with a G&T or a bowl of weed.
Any ritual built on two nights is a layup.
Keep the peace
Don’t fight, obviously. But if you do, give in. You can talk about it later if you must, but for the weekend, simply capitulate: She’s right. You’re wrong.
Don’t do what one guy I was with did and spend an entire weekend arguing about smuggling contraband kosher brisket into Turks and Caicos.
Just suck it up and forget about it. Please.
Remember: it's not about you
Improper assignations work best when you make her feel attended to, cherished, and spoiled. (My favorite pampered weekend: an oyster dinner in suburban Connecticut, an unremarkable hotel, and unforgettable sex; lather, rinse, repeat.)
And here’s the special sauce: If you take care of her, she’ll take care of you back. That’s the beautiful circle jerk of love. Once you make it all about her, it’s really all about you.
A dirty weekend is easy if you keep the stakes low: It exists for sex, nothing more, nothing less. That being said, do it right and the goodwill it spawns can last for weeks, even years.
You both deserve a two-day horizontal timeout right now.
