Ask Isaac: I Want to Have a One Night Stand

Isaac also shared his thoughts about STDs, closure and Ashley Madison

Hello friend!

This is kind of a tough one for me because I’m not a fan of the one night stand. Making out with strangers? Great. But getting naked with someone who you’ve just met, then rolling around on a bed while they’re fumbling around down there or you’re fumbling around down there, neither of you really knowing how to make the other person feel good…it’s all kinds of awkward.

Then, there’s the dilemma of sleeping over or leaving in the middle of the night, or asking the stranger to leave if you guys hooked up at your place; not to mention how to behave toward each other the next morning. I could go on, but what you asked for were tips, right? SO:

1. Use a condom. For god’s sake, use a condom. According to Planned Parenthood’s website, “If you follow the instructions and use [condoms] every time you have vaginal, anal, and oral sex, there’s very little chance of pregnancy and your chance of getting or giving an STD is much lower.” Your health is worth so much more than checking something off of your bucket list.

2. Do the sex at your hotel (if on vacation)/house/apartment. It’s so much easier to relax on your home turf.

3. Communicate the rules of sleeping over (and amount of hang-time post-sex) before the sex happens. If you want your partner in one-night-standing to leave immediately after the act, explain that you have an early morning and need a solid night of solo sleep. But again — do this before. No one wants to be taken by surprise and kicked out at 3 a.m.

4. Communicate what feels good and what doesn’t! This person doesn’t know you, and you don’t know this person. Be sure to guide each other so that it’s a positive experience for both of you.

5. If you’re going to drink before, it’s important to know your body — drink water and keep your wits about you. There is nothing worse than waking up, hungover, next to a stranger who you don’t recognize. A stranger who has really bad morning breath.

Actually, worse is not recognizing the street you’re on. Worse than that is realizing you two didn’t use protection.

So bottom line: Stay safe.That’s the most important thing. And have fun! That’s important, too. Tell us how it goes. We’ll be here waiting for you!

Have a question for Isaac? Send it to with ASK ISAAC in the subject line.

Check out Isaac’s Instagram, Twitter and website; collage by Krista Anna Lewis; Isaac photographed by Melodie Jeng.


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