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“Uh oh!”… When Sex Goes Sideways

Think about your sex life as The Amazing Race For Pleasure.

Make sure you look all the way down this email, {FIRST_NAME Lover}.

Right now, I have nine ideas captured in a list on my phone called “Sexual Bucket List.” Every time I think of something new I want to try sexually, I take note because I know I’ll forget in the heat of the moment.

Variety and novelty keep sex hot between long-term partners. When you try new things together — you fuel new relationship energy — even if you’ve been together for thirty years like my husband and I.


Right now, I have an extensive list. Some line items are sexy adventures, like making love in the rain or trying the new Manta men’s pleasure toy while orally pleasuring my partner. Yet others, like a discussion around different ways we can enjoy morning sex: Can we brush our teeth first; how will I be warmed up enough to enjoy intercourse if we don’t have a lot of time for foreplay; and how do I keep my day’s action items out of my head enough to focus? 

Sometimes, my partner generates new ideas. Together we are a fountain of sexy fun, always coming up with things we want to try. My guy thinks of things that would never occur to me, and vice versa. Sharing fantasies is one of the best parts of a couple’s play. 

When you make a Sex Life Bucket List, there are three categories of ideas:

A: This is something I want to try.

B: It’s not on my list, but I’m in if my partner wants to try it!

C: This is not for me right now (but my sexuality is constantly evolving, so I keep my options open).

When you try new things, you aren’t good at them yet. See that I wrote “spanking lesson,” not “spanking.” That’s because my intention for the date is to have an erotic playdate where I coach my partner by giving me a spanking. I want to feel my way through and ask him to try a lot of things: best spanking position, hand vs. paddle vs. flogger, warm-up little soft spanks, spanks on different areas of my butt, harder spanks that are not slaps, smooth rubs to spread the sensation, what to do if a spank is too firm and hurts (because I want to spank for sensation, not pain), aftercare needs… and whatever else occurs to me at the time. He will want more feedback than I would typically provide if we had experienced together with spanking.

That’s what’s excellent about erotic playdates. If I just asked him to spank me, I probably wouldn’t like some things because we need to practice. Erotic playdates are sexual adventures where you try new techniques together. They leave room for learning. You’re just “trying things,” so you don’t feel bad about it when it doesn’t work out perfectly.

It’s best to take that attitude into everyday sex as well. “I’m just trying things” is a good response when your partner says, “Ew! What are you doing?” That sends a signal that everything is ok and that your contraction or feedback is just that, feedback — NOT failure in any way.

If things don’t go off as planned, or an unplanned situation happens, and somebody gets upset, talk it out. What specifically triggered the upset? How can I prevent this from happening again? What outcome were you expecting, and what was wrong with what occurred? Get the details because what you imagine is the issue is likely not it. Find out where it went sideways and talk through the particulars. That way, you can avoid making the same mistake twice. This kind of communication hygiene paves the way for much less stress talking about anything that needs to be said regarding your sex life.

Whether it’s a technique, a new toy, a new location, or a new partner, consider yourself a lifelong sexual learner. Your sexual maturation is a facet of your personal growth. When you have a growth mindset about your sexuality, it creates space for imperfection.

Often, the best memories a couple has are when sex went sideways. His penis popped out. There was menstrual blood on his face. You couldn’t get the toy turned off in the middle of an intense orgasm. They over-imbed and fell asleep. The bed broke (again)! She rode you so hard you lost your erection because you were afraid she’d break your penis. These are just everyday experiences that you may ultimately remember with humor.

When you get the perspective that is trying new things means you’re a beginner, it removes much of the performance pressure. Laughing and having fun, being extra communicative, and treating your sexuality like a life adventure captures a growth mindset. Think about your sex life as The Amazing Race For Pleasure. You are in it together to win and have a grand journey. 

As an intimacy expert, I’ve realized that over the last twenty years my fans want permission, inspiration, and education. Inspiration takes the form of sexy ideas lovers can try together, and solo experiences singles can enjoy keeping them sexually vital. Though I’ve created hundreds of techniques that transform having sex into making love, my sexy date night ideas continue to be massively popular. Bedroom boredom is only inevitable if you aren’t trying new things together. Couples that play together stay together, especially in the bedroom. 

The significant categories of new adventures could include new sex positions, sex in new locations, learning new sex techniques together such as having an Expanded Orgasm practice, becoming a multi-orgasmic man, or trying Tantric sex, role play, incorporating others into your play, and trying sex toys, lingerie, and sexy shows, combined with sexy dancing and photo or video shoots. Your sex life can only evolve if you allow yourselves to be imperfect beginners. Your sexuality is a gift that can give you lifelong pleasure and vitality. 

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