How To Have Successful Casual Sex Everyone Feels Good About

"Oh, that's so easy," you may say. Did you see the "everyone feels good about" part?
Publish date:
June 4, 2014
casual sex, hookups, fwb, M

"I am not DTF," I clarified to a friend recently. "Well, I mean, I suppose I am DTF -- but I'm like a super picky DTF. I'm SPDTF."

Then I laid out to my friend my magical formula for casual sex that everybody can feel good about. Which keep in mind, I've used exactly twice now, but I still think that's enough to prove it's a winner.

Step 1: Make it clear in your dating profile that you are open to a purely hookup scenario.

This may seem obvious -- but for a long time, I actually didn't say anything like this. Then I realized, the truth of the matter is: I don't even want to date most of the guys that I meet for a dinner date. So I usually make it coffee. And even then, it can often feel like the most arduous job interview ever -- or like an unpaid consulting gig. I'm watching the clock the whole time, and at 45 minutes in, I find some excuse to leave. So I tried to be more realistic. I wrote on my Tinder "Looking for a long-term serious thing but not averse to a good FWB situation since work takes up the majority of my time." There we go. And, presto. I've just saved myself hours and days of figuring out what page everyone is on. Sure, I absolutely want love. Sure, I absolutely want a great relationship. But if I don't find that -- man, does getting the D from someone who knows how to give it feel freaking awesome.

Step 2: Be safe and also only meet people who you actually want to meet. Vet accordingly.

I like Skype and FaceTime for talking to someone ahead of time to see if you're on the same intellectual wavelength. That may not be important to some people, but I find myself attracted to personality and intelligence over all else. Looks are great, but there has to be that X factor of mental spark at play. Talking on FaceTime also allows you to see someone in their office setting. Unless there were some elaborate long-game machinations at work where someone has rented out an office, hired actors to play their co-workers, etc., this is a nice way to be able to guarantee that -- take for example, in my case -- an editor is really an editor.

Step 3: When you do chat, bring up the sex thing in a coy but direct way.

My line that I just used successfully (and which I meant): "I have a lot of writing that needs to get done but part of me feels like hooking up might be a stress reliever." The response I got back from the dude: "Um? If I can be of service?" The next time me and this dude hooked up it was also a good callback. He arranged it very quickly with a text: "Any desire for a stress relief today?" Answer: "Yes, please."

Step 4: For your first get-together, meet at a bar or coffee shop near your place.

Suss out potential attraction in the next 30 minutes. If you're both game, you're not far from home.

Step 5: In your super-sped-up "date," make sure there is a basis of respect underneath -- for later.

I honestly think this is the main factor where people can go wrong. (Or where I've gone wrong, anyway.) Something casual can be so great and refreshing -- but ONLY if you feel good about it afterward. For me, I know I feel good when it's two people essentially going to the happy sex gym together. What ruins it for me is when I can tell that after all is said and done, the guy thinks I'm some less-than discardable slut. (Mainly, this has happened to me with a few guys in their 20s. So, good job, thirty-something guys.) But you can tell what someone's philosophy toward women is through a brief conversation ahead of time. Be frank, and you'll get a frank response. "So what do you think of the fact that I'm just interested in hooking up with you?" If he responds with something like, "Hey, man, I suppose it takes all kinds," then, ew. If he says, "Yeah, I get it, I'm so overloaded with work I have zero time to date right now, too," then ding ding ding this could be your guy.

Step 6: Set the fun casual sex mood with the right music and mood lighting.

You don't want, like, a bunch of candles. One is perfect. As for music, I'm actually really curious as to everyone's music for sex recommendations. I need to synch my music on my damned iPhone so I don't have a ton of it available right now (shouldn't it be in the Cloud? IDK) -- just some random records on there, here and there. Because of this, I went straight to the most moody thing I could think of, and started up the "Drive" soundtrack. Except that when I listened to it, I realized just how ethereal everlasting death love the entire thing is. Not the right mood. Not the right mood at all. But as I was browsing through albums, I realized -- yes! -- The Strokes is kind of the perfect background sex music. Jangly, fun, sexy, catchy, no big. I think Bowie is probably a pretty solid choice, too. Evocative, more conceptual, not too serious.

Step 7: Be prepared to call out how this is awkward so that everything becomes a whole lot less awkward.

When you're at your place, say something like, "Want a glass of water?" Not, like, "What was your last relationship like?" Or, "Do you really think anyone who voted for Nader cost Gore the election in 2000?" It's easy to slip into more serious kinds of questions as they're a natural part of conversation, but for this scenario, keep it in the moment and superficial. "Is this candle okay?" "Do you want to take off your coat?" "I like your gingham shirt." Anything, but -- "Tell me about your hopes and dreams and do you think the world as we know it will even exist 20 years from now and what will that mean for our children's children anyway?" No. Talk about the dumb candle. "That candle sure is on fire, right?" [Removes a piece of clothing.]

Step 8: Make a move if the other person doesn't.

Kiss! Slow and hesitant is sexy. But just do it. Just kiss him. Or let him kiss you. Are you attracted? Was the kiss okay? Unless the kiss is awful, I say give it a good one to two minutes to figure out what the attraction level is. Some guys kiss like their tongue is doing gymnastics -- or like they're auditioning for where they might kiss later -- which isn't really my thing, but it's not terrible. I think it can work if the overall chemistry is good enough. The first two minutes will tell you what you need to know if you want to go further. [Removes a second piece of clothing.]

Step 9: There's no shame in calling it all off.

I've sent people home with cab fare money when I didn't feel it. Like I said, I'm SPDTF. Of course, the guys have refused the cab fare money, but, you know, it's a nice little button to put on the whole experience. "I do not want you. Here is $20 because I feel bad you took a cab. Oh, I can keep it? All right. Anyway. Goodbye forever."

Step 10: If you are going to do the deed, obviously be prepared for safe sex and communicate the fun stuff.

Condoms. You gotta have 'em. Now, for the fun stuff part: I love psychological teasing and languid touch. Pretty much anything that is the opposite of frenzied jackhammering. Usually if there is a chemistry match, you don't need to say some of the basics as it becomes more like a dance, an ebb and flow, but don't be afraid to communicate what gets you off. Not too much, but just enough words to make it as great for both of you as possible.

Step 11: Speaking of words, less is more.

Honestly, what do you have to say? Are you really interested in dating this person? Well, then you might be in for a world of hurt because your partner is probably just assuming this is only about the sex. Don't mistake that oxytocin sexytime rush for actual love or pair-bonding. I love when two people are on the same page about something. Make sure this is the case with your FWB situation, otherwise it will become your Friend Who (is a) Bummer situation.

Step 12: Get in, get out.

Kiss goodbye, tell them to have a great day, say it was fun, whatever. Of course, intimate post-coital conversation can assist in leading to something that could spring from the purely physical, but if that's going to happen, then it will happen. If you push it, you're just going to get hurt. If you know exactly what your situation is, you'll feel good about it. I honestly think that is a big mistake that a lot of guys make with women -- is feeling like they need to create some Potential Boyfriend Illusion pre-sex to give the woman a nice cozy feeling, when really that's just a crappy bait and switch. All the two of you have to do is be direct and honest. Are you suddenly wanting something more than casual sex? Cool. Again, just be direct. You have nothing to lose! (Except for a FWB! But that's a risk worth taking!)

But back to the whole music to listen to during sex question, anyone have any good recommendations? Rolling Stones, perhaps? White Stripes? "Some Kind of Wonderful" soundtrack? What you got?


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