DEAR ROCKY LOVE: Prepare for casual sex

By on October 14, 2014
Rocky Love

Rocky Love

Dear Rocky Love,

I’m a recently divorced woman in my early 40s. I’m not ready to be in a relationship again, but a woman sometimes has needs that can’t be taken care of through the whole DIY mode. I met a guy who seems to be in a similar space. We had coffee, and he’s nice and attractive.

I figure he may soon invite me back to his place, and I’d love to go. I’ve been out of the dating pool for so long, I don’t know if there’s some sort of protocol about staying the night, or leaving by a certain time. Do I wait for an invitation to stay? Would it be presumptuous if it turned out that I had a toothbrush in my bag?

Once we are at his place, I have a bit of an intimate question: Do we need to use a condom for a blowjob? Sorry to be so graphic, but honestly, I’m feeling out of my depth. Is that sort of thing considered safe these days?

— Signed, Back in the Dating Pool

Dear Back in the Dating Pool,

Thank you for writing! I love letters like this because you break the ice about some important issues.

Let’s tackle the etiquette questions first. From your letter I get the sense that, for you, staying the night would be part of a complete date, and that even though you don’t want a relationship, cuddling up and sleeping together would enhance the fun. I say, forget the concern about protocol — I don’t think there is such a thing when it comes to casual sex. You two get to make up your own rules based on what makes you both comfortable and happy. For your first date involving sex, I’d suggest making the decision about staying the night together in the moment. He might bring it up. Or you can. You might want to see how the sex goes first because, who knows, maybe you’ll want to go home. Either way, keep it light and playful. Rocky Love is a fan of direct communication, but there’s no reason that communication can’t also be flirty and gentle.

As for the toothbrush, sure, bring one. You’ll be glad to have it if you do stay the night. But a word of caution — don’t brush your teeth before sex. That may sound counterintuitive, but that’s where the safer oral sex question comes into play. Brushing your teeth can open tiny abrasions in your gums, making the risk of HIV transmission higher. Here’s what my favorite sexual health resource, Planned Parenthood, has to say about oral sex and safer sex:

“When it comes to HIV, oral sex is safer sex than vaginal or anal intercourse. But other infections, like herpes, syphilis, hepatitis B, gonorrhea and HPV can be passed by oral sex. Use condoms or dental dams to make oral sex safer.”

I think one of the best things we can do to maintain our sexual health is talk to partners and potential partners. Also, get tested for the full range of sexually transmitted diseases. Ask Mr. Nice and Attractive if he’s been tested recently. Ask if he’s ever had an STD. Yes, these are seemingly far more awkward questions than “Should I bring a toothbrush?” But knowledge is definitely power when it comes to sex, allowing you to make informed decisions about what level of risk you’re willing to take. For more information and ideas on how to have that conversation, visit Whatever you decide, remember there are all kinds of sexy things you can do with someone that don’t include any exchange of body fluids. Who knows, maybe jumping back in the dating pool is going to expand your sexual repertoire in some very creative ways.

— Have fun and be safe, XO, Rocky Love

Dear Rocky Love is an advice column on dating, sex and relationships in the Tetons.Send your letters c/o JH Weekly, PO Box 3249, Jackson, WY 83001 or email:

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