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• Orgasming during masturbation is different than orgasming with a partner.

• Many people who can orgasm alone struggle to orgasm with another person.

• In order to orgasm you have to be able to relax and be present.

• Give yourself and your partner time and patience as you learn the skills needed to orgasm together.

HOUSEKEEPING

• I have an exciting announcement! Join me on July 24th at 8 pm ET / 5 pm PT for a Live Power Hour all about boundaries. You’ll get an email asking you to join me at the time of the talk. If you can’t make it live, submit a question in advance to be answered during the live talk. You can email me at caitlin@caitlinscouch.com.

• This talk is for paid subscribers. For just $5 per month, you get access to my live talks, the full archive of posts, the Paid Member Vault, and more.

The Post:

Some people can orgasm through masturbation but struggle when they’re with a partner. If that sounds familiar, you’re not alone, and there is nothing wrong with you.

Orgasming during masturbation is entirely different than with a partner. When you’re alone, you can focus, there’s no pressure, no anxiety, fewer distractions, and fewer worries. You know your body, and you know what you need. For many, insecurities surface when a partner is present, and it can be difficult to relax and focus. There are far more distractions when you’re with your partner than when you're alone.

This doesn’t mean you can’t orgasm with a partner. It means there are different skills needed to achieve orgasm when you’re having sex with another person. And it means you and your partner need time to practice those skills, just as there was a time when you had to learn how to orgasm through masturbation.

These are the three main skills you need so you can orgasm with a partner:

Learn to relax.

Stress and anxious thoughts don’t lead to orgasm. Most people have busy, stressful lives and often find it hard to relax. Relaxation is one of the keys to orgasm, so it's important to learn how to turn things off, get present, and relax your body.

To strengthen your ability to relax, you can tend to your nervous system on a regular basis with simple daily practices like exercise, for example. Regularly moving your body helps you better handle stress and anxiety, as well as increase your capacity for it, so you don’t get overwhelmed or distracted easily. You can also learn to use relaxation techniques in stressful moments. For example, to lessen anxiety and distracting thoughts in any given moment, you can learn to use deep breathing techniques to calm your body and to stay present. There are many strategies to increase relaxation, but the important thing is not to wait for it to happen naturally. Learn to make it happen, or you could be waiting for a long time.

Improve concentration.

To reach orgasm, you have to be able to focus on sensations and fantasies. If your mind is wandering all over the place, you're not feeling pleasure. If you're not feeling pleasure, you're not going to orgasm.

A regular meditation practice strengthens your ability to focus. It also teaches you how to recognize when your mind has wandered and to bring your attention back to the present moment, again and again.

You don’t have to meditate for hours a day to strengthen this skill. You just have to do it for a few minutes at a time with regularity. Over time, you'll be able to use the skills you learned through meditation to help you orgasm with your partner.

Tell your partner what you need.

You know what you need to orgasm when you masturbate. Your partner doesn’t know until you tell them. If you’re afraid to tell your partner what you need, it will be hard to orgasm with them, so communication is key.

You can start small by telling them one thing that will help increase your pleasure. Or, you can share your needs by writing them down, if it feels easier. When telling your partner what you need, be specific about what you want more of, rather than telling them what you don't want. Knowing what you don't want doesn't help them know what you do want.

Keep in mind that whenever we start doing something we’re not used to, it feels scary or awkward. Communicating about sex is no different. But the more you do it, the easier it gets. And when you orgasm with your partner, it will be worth having pushed through the awkwardness.

When you practice these skills, you’ll set yourself up for success because you’ll be able to be relaxed, focused, and present. Additionally, you’ll be able to communicate your needs to your partner, giving them the opportunity to learn how to meet those needs.

Make sure you practice being patient with both yourself and your partner, as learning to orgasm together takes time. Embrace feelings of awkwardness because any time we learn a new skill, it feels awkward until it gets comfortable.

Approach this with a curious mind, eager to embark on the journey. Don’t think of orgasming with your partner as a matter of success vs. failure, as that puts unnecessary stress on your orgasm. Remember that it’s about exploring and enjoying each other, not winning or losing.

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This blog was originally published on Psychology Today.

• A 50-year-old woman wants to meet the guy she’s been messaging with on a dating app, but she’s worried he has the wrong impression of her because they talk about sex a lot.

• Boundaries can be set at any time, regardless of what was said before.

• Pros and cons of talking about sex early on.

• The way someone behaves is a reflection of who they are, not you or your worth.

HOUSEKEEPING

• I have an exciting announcement! Join me on July 24th at 8 pm ET / 5 pm PT for a Live Power Hour all about boundaries. You’ll get an email asking you to join me at the time of the talk. If you can’t make it live, submit a question in advance to be answered during the live talk. You can email me at caitlin@caitlinscouch.com.

• This talk is for paid subscribers. For just $5 per month, you get access to my live talks, the full archive of posts, the Paid Member Vault, and more.

THE POST:

Dear Caitlin,

I’m over 50 and met a man who is also over 50. There is a very strong attraction. We started talking via chat about sex about a week and a half ago. We have not made arrangements to meet, but we find our conversation about sex is more interesting than, What are you doing and How is your day. He gives compliments and so do I. Because we met on a dating app I know there are others he maybe talking to, but everytime I have a conversation I wanna hold his attention and leave him wanting more later. In my opinion that keeps him attracted. However, I wanna be DREAM GIRL status and not THOT status cause we started off talking about sex. Please help. 🙏🏾

R.K.

Dear R.K.,

It's easy to go from light flirting to heavy sexting when you first start talking to a new person on a dating app. Like you said, you’re attracted, it’s new, fun, and exciting. However, once the conversations are all about sex, it changes the dynamic and makes a relationship less likely to develop.

First of all, your focus becomes about sex, rather than getting to know each other. If you’re looking for a hook-up, that’s fine. If you’re looking for a relationship, you need to get to know each other and see if you enjoy talking and spending time together. Conversations about sex might feel more interesting with this person, but you want to find someone you enjoy talking to about a variety of things.

Second, expectations change. If you start out talking about sex, when you meet, the expectation is to continue talking about it more. The more you talk about it the more turned on you get, and the more likely you are to have sex before getting to know each other. This is how a lot of situationships get started.

Could you do both—talk about sex (or start having sex) and get to know each other at the same time? Of course, that’s possible, but it’s the exception not the rule, especially with heterosexual pairs.

The good news is, there is still time to change course because you haven’t met and you haven’t had sex yet. To do this, you have to let this man know you’re not comfortable talking about sex all the time so early on because you’re looking for a relationship and you want to get to know him better. Let him know you enjoy talking about sex with him, and hope at some point you’ll go back to it. But for right now, you’d like to put the topic aside. If he agrees to do that and respects your boundaries, you can get to know each other and develop a connection. If he doesn’t want to put it aside or agrees to but then doesn’t respect your boundaries, he’s showing you who he is, and he’s not the right person.

If things don’t go well, it’s important that you don’t beat yourself up for talking about sex early on. People often think that if they hadn’t, things could have worked out. In reality, if this person isn’t willing to put it aside and get to know you, he probably isn’t looking for a relationship regardless of what he said. Someone who is looking for a relationship will be fine with getting to know you and respecting your boundaries is a green flag.

I hope this helps!

Xo,

Caitlin

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Mantras for connecting to your inner sex goddess. Click below for a list of mantras that will connect you with your inner sex goddess. Download either a PDF or a phone background to remind you how amazing you are every time you unlock your phone. Check out the I AM SEXY MANTRAS!

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If you're struggling to find an amazing partner & create the relationship you long for, it's not because something is wrong with you. Most likely, you're unknowingly getting in your own way.

With this list, you will see 10 possible ways you're getting in your own way and what the solutions are. Once you know how you're getting in the way of creating the relationship you want, you can start doing things differently so you can move forward & build the future you dream of. Check out 10 DATING MISTAKES THAT ARE KEEPING YOU SINGLE, today!

Start sating NO with confidence and clarity! Your first dose of empowerment is waiting for you. These skills will elevate your sense of self-love and help you create the healthy relationships you wish for.

I've been a therapist in private practice for over a decade. In that time, it became clear to me that most people were not taught how to set healthy boundaries-the number one skill needed to create healthy relationships! Check out 12 WAYS TO SAY NO WITHOUT THE GUILT, today!

None of us were taught how to create the amazing relationship we want, so it makes sense that it can feel impossible at times. After all, what do you do well that you were never taught how to do?

The good news is, now you can get the relationship education you need. Once you learn the key relational skills and practices, both you and your relationship will change for the better. You will go from feeling lonely, resentful, & helpless, to feeling loved, empowered, & deeply connected to your partner - even if your partner isn't doing the work with you. Check out, 10 SECRETS TO A HAPPY AND HEALTHY RELATIONSHIP, today!

After working with hundreds of couples for over a decade, I found that the happiest, healthiest couples have specific habits that keep their relationship loving, romantic, and thriving. Whether there are issues in your current relationship or you want to prevent issues down the road, practicing these 10 HABITS OF HAPPY COUPLES, will make a world of difference.

As you know from experience, the online dating world is a total shit show. You have to learn how to work it or it will chew you up and spit you out.

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A list of potentially non-sexual pleasurable experiences you can try as part of your journey toward changing your relationship to pleasure. You can do something on this list, or let the suggestions spark new ideas to try.

Try to do something pleasurable every day as a form of self-care and self-love. Check out your guide today.

Watch the replay of Caitlin's Q&A all about boundaries.

A list of journal prompts to sit and reflect. All about identity awareness, self- acceptance, and self-empowerment. Click here to download the guide. Grab a notebook, or print off the guide and find a quiet spot to reflect.

A list of potentially non-sexual pleasurable experiences you can try as part of your journey toward changing your relationship to pleasure. You can do something on this list, or let the suggestions spark new ideas to try.

Try to do something pleasurable every day as a form of self-care and self-love.

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Most people want a relationship, but are you sure you're really ready for one?

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Take this quiz to find out your Unique Argument Style! Stop having painful fights and start having better arguments that bring you closer.

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After working with hundreds of couples for over a decade, I found that the happiest, healthiest couples have specific habits that keep their relationship loving, romantic, and thriving. Whether there are issues in your current relationship or you want to prevent issues down the road, practicing these habits will make a world of difference.

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None of us were taught how to create the amazing relationship we want, so it makes sense that it can feel impossible at times. After all, what do you do well that you were never taught how to do?

The good news is, now you can get the relationship education you need. Once you learn the key relational skills and practices, both you and your relationship will change for the better. You will go from feeling lonely, resentful, & helpless, to feeling loved, empowered, & deeply connected to your partner - even if your partner isn't doing the work with you.

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Start sating NO with confidence and clarity! Your first dose of empowerment is waiting for you. These skills will elevate your sense of self-love and help you create the healthy relationships you wish for.

I've been a therapist in private practice for over a decade. In that time it became clear to me that most people were not taught how to set healthy boundaries-the number one skill needed to create healthy relationships!

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If you're struggling to find an amazing partner & create the relationship you long for, it's not because something is wrong with you. Most likely, you're unknowingly getting in your own way.

With this list, you will see 10 possible ways you're getting in your own way and what the solutions are. Once you know how you're getting in the way of creating the relationship you want, you can start doing things differently so you can move forward & build the future you dream of.

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Learn to communicate better with this healthy communication checklist. Learn new communication skills so you can stop fighting when you talk about tough topics, and so you can feel more connected in general.

Download Now

Are you tired of talking about self-love, but not actually feeling self-love?

Are you frustrated because you understand why you don't believe you're enough as you are, yet you still feel unworthy?

If you're tired of talking about self-love, and you're ready to start actually loving yourself and knowing your worth, you need Ten Ways to Start Loving Yourself Today.

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• The things that fostered desire in the past stop working as your life and relationship progress.

• Sex has to be good so it's worth having when you're tired and have a lot of other obligations.

• Communicating your needs is necessary to have better sex.

• If you don’t prioritize pleasure outside of sex, you won’t prioritize it in a sexual context.

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THE POST

Do you ever wonder why you never feel like having sex anymore? If you used to feel desire in the early years of your relationship, but now it’s the last thing on your mind, it’s possible you aren’t having sex worth having.

In the beginning of your relationship, everything was new and exciting, being desired was a turn on, and knowing how happy sex made your partner motivated your inner people pleaser. Those are great reasons to have sex. However, as time passes and the relationship progresses, those reasons become less effective. The relationship isn’t new anymore; being desired starts to turn you off because it feels like pressure, and having sex because you know it makes your partner happy isn’t enough of a reason when you’re exhausted from life’s increasing demands. For these reasons and more, what initially fueled your desire no longer works. That’s not because something is wrong with you or your relationship. It’s because you’re at a different stage of your life.

Now, you need different reasons to have sex. One of those reasons needs to be that the sex is worth having, despite all your other obligations and regardless of how exhausted you are. If it’s not that good, you won’t prioritize it, and you won’t feel desire.

While there are many ways to have better sex, there are two key factors that make it possible. First, you need to ask for what you want. If you don’t feel comfortable asking, it won’t get better. People pleasers often struggle with this because they are highly skilled at caring for others, but less skilled at asking for what they want and receiving it. If you’re not used to asking for what you want and receiving it, it will feel awkward and uncomfortable at first. Try to hang in through the discomfort that comes with the process of change. Give yourself time to practice, and eventually it will feel easy.

The second key factor that makes it possible to have better sex is your relationship to pleasure. It’s hard to have sex worth having if you don’t value pleasure. Sometimes we don’t value pleasure because we were taught it’s not important. In a society like ours, which prioritizes productivity, it makes sense that many people deprioritize pleasure.

Some people struggle to prioritize pleasure because they believe their value comes in their ability to please others. They don’t feel worthy unless they can make others happy. When your worth depends on pleasing others, you spend your life seeking ways to give pleasure rather than receiving it. Just as asking for what you want is a skill you can hone, so is receiving it. Give yourself time to practice receiving so that, over time, it will feel good.

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To begin addressing your libido struggles:

1. Explore your relationship to pleasure. What messages did you get about pleasure? What was modeled for you? What would you like to believe about pleasure? What do you feel when you hear the word pleasure? How do you feel when you say it? You can journal about these ideas or discuss them with your therapist.

2. Start prioritizing pleasure in non-sexual contexts. If you don’t prioritize pleasure outside of sex, you won’t prioritize it in a sexual context. Notice how you feel on days you’ve prioritized pleasure. Do you feel more energy? Less energy? What else do you notice?

3. Practice asking for things and receiving. Start asking for things you want or need in non-sexual contexts first. For example, ask for help and let others help you. Let others go out of their way for you. Notice how it feels to receive. Notice how it feels when you ask for something and don’t get it. Let these practices be uncomfortable until they feel more familiar. When you feel ready, ask your partner for what you want in a sexual context. Feel free to start small. Continue to practice asking and receiving until it feels easier.

While there are other ways to have better sex, asking for what you want and being able to receive pleasure are always necessary. Pleasure is essential for overall wellness, so it’s important to work on having more of it in your life. Plus, life is short, and you deserve it!

This blog was originally published on Psychology Today.

POST SUMMARY

People pleasing isn’t always a bad thing. In a healthy relationship, it feels good to please our partners. When we go out of our way for them and it makes them happy, it also makes us happy. It becomes unhealthy when no matter what you do, they’re never pleased, or if you measure your worth based on pleasing others, or if you consistently abandon yourself for someone else. This post will show you how to be a healthier people pleaser. You’ll learn:

• How to recognize when your desire to people please is unhealthy for you

• What to do instead

• How to elevate your self-esteem without needing approval from others

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THE POST

My mom once had an aide named Lucy who seemed really cool. She was friendly, funny, and helpful. Over time, however, I noticed that Lucy took time off whenever I visited my mom. At first, I thought she wanted time off when I was there, so my mom wouldn’t be alone. But helping my mom and taking care of my family was a lot for me, so I decided to ask my mom about it.

My mom hadn’t noticed the pattern, but when I pointed it out, she decided to talk to Lucy about it. The problem wasn’t just that it was hard on me to take care of everyone, but also, my mom couldn’t spend time with Gabby (my daughter) without Lucy there to help. Gabby and my mom wanted to spend time together, so Lucy needed to be there for our visits.

After speaking to Lucy, my mom found out that Lucy didn’t like being there when we visited. She said there were two reasons. First, she didn’t want to be a babysitter. Second, it bothered her that we were messy. My mom told her she needed help to take care of Gabby, and that was a non-negotiable for her. If Lucy wanted the job, that was part of it. It was only a couple of times a year, so Lucy conceded (round of applause for my mom setting a boundary👏).

While Lucy’s attitude toward my daughter bothered me, I put those feelings aside because my mom is hard to please, and their relationship was mostly good. I didn’t want to come between them.

As far as being messy, I agreed with her. I fully admit that being neat and tidy isn’t my strong suit and never was. So, I agreed to be less messy and to honor her specific requests for how she wanted things done while we visited.

During our next visit, I was a temporary neat freak. You couldn’t tell that there were three additional people in the house. My mother commented on how shocked she was, and my husband said he didn’t know I had that in me. I was careful to put the towels where she wanted them, not to leave a dish out, and to make sure everything was exactly as we’d found it.

Then, on the last day of our visit, my daughter was playing and made black marks on the floor. Lucy, exasperated, said, "Look at those marks on the floor!” and ran into my mother’s room in a tizzy to tell her about them. I jumped up, worried the marks were permanent because Lucy was so upset, and began wiping them up. They came out easily. That’s when I realized that Lucy was an unpleasable person.

Trying to please unpleasable people is a painful journey that never ends. No matter how hard you try, it’s never enough. Eventually, resentments build, you abandon yourself more and more, and your self-esteem takes a nose dive.

Once I realized that no matter what I did, Lucy would find something to complain about, I stopped trying so hard. I felt sad about it. I wished she weren’t so unhappy when we visited. I could have let my sadness lead me to work even harder next time, but there would always be something. So instead, I let myself feel sad and didn’t try to fix it. Then, I got clear on what I thought was right in the situation. I wanted to be the kind of guest who I’d want in my own home. Going forward, as long as I met my own standards and did what aligned with my values, I felt good about it and good about myself. When Lucy complained, I let it go in one ear and out the other. I chose to make my own voice the loudest, not hers.

From then on, I felt more relaxed on our visits because I knew my standards and could meet them. If I continued trying to please Lucy, I’d feel anxious, never knowing where she’d move the goalposts.

Unpleasable people complain because that’s how they are. It’s a thought pattern and a habit for them. Someone who finds things to complain about or criticize will always find those things. That’s why it’s important to stop taking it personally.

If you’re a self-proclaimed people pleaser, make sure you’re not trying to please someone who is never satisfied. If you’re in a relationship where you never feel good enough—this could be your partner, parent, boss, friend, etc—there’s a good chance the problem is the person you want to please, not you. The first step in changing this painful dynamic is to recognize it. If you realize that you can’t please the person no matter how hard you try, get clear on your own standards. If they criticize you, think about whether or not you agree with their point. If you do, let it inform you of your own values and change the way you do things going forward. If you disagree, keep doing things your way. No matter what, don’t let their criticisms inform you of your worth. Your worth isn’t in question, nor is it dependent on what this person thinks of you or getting their approval. Remember, only you have the power to define your worth.

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• Pleasure is necessary for overall health and wellness

• Your relationship to pleasure in general (not just sexual pleasure) impacts how you feel about sex

• Not prioritizing pleasure in your life contributes to feeling exhausted and unhappy

• New resource available for paid subscribers in the Paid Member Vault

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Pleasure is necessary for your health

Pleasure is key to our overall health, but most people, especially women, have complicated feelings about it. We’ve been conditioned to believe that pleasure isn’t important. We feel guilty about putting ourselves first and prioritizing our pleasure. We’re taught that rest should be earned and pleasure is gluttonous, bad, and even sinful. We’re told to be productive above all else, and that our productivity correlates to our worthiness. That means prioritizing our pleasure comes last if it makes the list at all.

The problem is, when we don’t make pleasure a priority, we create an imbalance between the energy we expend and the energy that nourishes us. As a result, we feel less happy, we’re more exhausted, we’re less productive, we’re less able to manage stress, and we're less healthy. We’ve been told we don’t need pleasure, but if we want to thrive, we do.

Prioritizing pleasure is a powerful form of self-love and self-care. We need pleasure to nourish us and to give us energy. Just as we get injured when we overwork our bodies and don’t rest and recover, we get ill when we focus on our to-do lists and productivity and don’t replenish with pleasurable activities.

If you’re tired of feeling unhappy, exhausted, and drained, and you want more energy and to feel healthy, it’s time to change your relationship to pleasure.

Pleasure and Sexual Desire

If you don’t prioritize pleasure in general, it makes sense that you don’t prioritize sexual pleasure. If you don’t prioritize sexual pleasure, it makes sense that you don’t feel desire for sex. It all connects back to your relationship to pleasure in general. If you struggle with low libido, addressing your relationship to pleasure in general can help.

Changing your relationship to pleasure

The first step to working on your relationship to pleasure is to start prioritizing non-sexual pleasure on a daily basis. Non-sexual pleasure can be physical, emotional, intellectual, spiritual, and relational. What you experience as pleasure is deeply personal and varies from person to person. You may already know what you find pleasurable, or you might have no idea. Regardless of where you are with your relationship to pleasure, going on a pleasure exploration journey can help you discover what you find pleasurable and help you see the value of bringing more pleasure into your life.

To help you discover what gives you pleasure and explore the experience of pleasure in more ways, I created The Non-Sexual Pleasure Exploration Guide. I provide specific examples of pleasurable activities in each category for you to try. You can download this guide and access all the guides in the Paid Member Vault on the Caitlin’s Couch Substack when you become a paid subscriber.

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In this heartfelt episode of Caitlin’s Couch, Caitlin shares a deeply personal story that sparked an essential lesson on the power of appreciation in relationships. After a long and difficult chapter supporting her husband through a decade-long PhD journey, a simple yet emotional moment of genuine gratitude from him reminded her just how impactful heartfelt appreciation can be. Caitlin breaks down why appreciation isn’t just a “nice to have,” it’s foundational to intimacy and connection. She introduces a practical, 3-step process for expressing appreciation in a way that truly makes your partner feel seen, valued, and emotionally connected. Whether you're in a long-term partnership or just beginning one, this episode will leave you reflecting on how you give and receive love and how to do both more meaningfully.

Key Takeaways:

• Appreciation is foundational, not optional in a thriving relationship.

• Emotional expression and specificity are what make appreciation land.

• Many people struggle with expressing and receiving appreciation, but it’s a skill that can be learned.

• Feeling truly seen can be healing, even if we didn’t know how much we needed it.

If you enjoyed this podcast, check out these related posts:

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Disclaimer

Key Takeaways:

1. The Reality of Long-Term Relationships & Intimacy – Sex in a committed relationship evolves from the early days of passion and novelty to something that requires intention and effort.

2. Maintaining Connection Between Sexual Experiences – Connection isn’t just about sex itself; what happens in between is just as important.

3. Bridging the Gap in Different Connection Styles – Some people need emotional closeness before being available for sex, while others need sex to feel emotionally close. Understanding and balancing these differences can lead to a stronger relationship.

Resources Mentioned:

• Read Caitlin’s latest Psychology Today article on maintaining connection: Simple Non-Sexual Daily Practices for Maintaining Intimacy

• Listen to the latest blog post from Modern Sex, Caitlin’s blog on Psychology Today:

• Listen to and read more content on Caitlin’s Substack:

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The relationship & sex education you didn't know you needed.

By Caitlin Cantor, LCSW, CST, CGT

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