Advice

A Step-by-Step Guide to Parlaying Your One Night Stand into a Second Date

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You wake up next to a stranger. Surprisingly, you like what you see. Don’t panic. This CAN, in fact, happen on occasion. Unfortunately — and I’m not really sure what this says about our culture, but it can’t be good — you might be facing an uphill battle when it comes to ever again seeing this person whose uglies you just bumped. Which is really a shame, because chances are you rock.

Precedent dictates that you’ve got about a one-hour window before what’s-his/her-face flees your apartment (or kicks you out on the street). That means time is of the essence. Follow this simple step-by-step guide and you might just convince your new friend that you’re worth stumbling home with again in the future.

Plus: 9 Ways To Get Him To Leave Your Apartment The Morning After

First thing’s first: locate your underwear. Put them on.

Now that your immodest parts are under wraps, head to the bathroom as stealthily as possible. Be careful not to wake Sleeping Beauty. Once there, brush your teeth. If you’re not at home, forage for mouthwash or brush with your finger. Morning breath may be unavoidable, but it’s a massive obstacle to the morning-after make-out you are about to initiate …

That’s right: upon returning to bed, don’t be afraid to kiss her/him! Isn’t it insane that such a kiss can actually be really intimidating, considering the fact that you just slept together? Time to channel your inner Nike: Just Do It.

After playing kissy-face for a bit, you’ll want to share some good pillow talk. Rolling over and pretending to sleep is a surefire way to expedite your bed-partner’s departure. That moment when she/he wakes up and wonders “Where the f*ck am I?” is not a pleasant one. A good conversation will affirm that you are not an axe-murderer and cut the tangible tension that always hangs over a room laced with regret and the dewy afterglow of drunken sex.

Plus: 36 Reasons She Didn’t Hook Up With You Again, As Told By 36 Real Women

Guys: if you’re at your apartment, offer her a pair of gym shorts and a t-shirt. My experience tells me (not me personally; rather, some guy I know) that no girl likes to put the complexly strapped and debatably comfortable ensemble she wore last night back on in the morning, and if she does, she’ll probably make haste for the door soon after.

Now it’s time for the showstopper: make him/her breakfast. Or at least coffee. If you’re not at home, suggest going out some place. It worked for Seth Rogen in Knocked Up. Well, that plus the whole unexpected-pregnancy-equals-forced-obligation thing.

By now, so-and-so will probably want to get on with their day, so don’t overstay your welcome. No matter how golden of an impression you are making, you always run the risk of coming off as desperate or clingy. Secure the digits (I always doublecheck for fake numbers by dialing the number as soon as it’s dictated to me), express once more how great of a time you had last night, and then ride off into the sunset.

Plus: 10 Surprising Perks Of The One Night Stand

Of course, there is one more maneuver you can pull, but it’s certainly not for the faint of heart, as you’ll be risking the loss of one of your possessions. Yes, to those of you shaking your heads in disbelief, that’s exactly what I mean: intentionally leave something behind. Girls should try a pair of earrings or some other piece of jewelry, as long as it’s not an heirloom or something worth appraising. Guys have it tougher. Baseball caps are ideal; belts and undershirts will suffice in a pinch.

The work doesn’t end there, though. Send a text later in the day, a reminder that you’re still thinking about last night, rather than trying to purge the memory of it from existence. Try something brief and witty that refers to the previous night’s escapades (“My big toe is killing me. How’s your bedpost holding up?”).

Once you’ve reached out, put things on ice for a few days. I hate perpetuating hard-and-fast dating rules, but in this situation, three days does, in fact, seem like a good interim period before soliciting another hang-out.

Should she/he agree to see you again, congratulations! You just successfully parlayed a one night stand into a second date. There is one lesson left to consider, and it is perhaps the most important: temper your expectations. Just because you two got drunk and made some mistakes together does not automatically mean that the sex boundary has been permanently crossed. Assuming that it has could prove to be a huge turn-off and sabotage all the work you just did to put yourself in this position.

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