Intimate questions answered with
grace and confidence - Part three

SEXUAL ISSUES AND CONCERNS FOR SINGLE WOMEN IN 50s & 60s

Q: Re-entering the dating scene seems nearly impossible, dating sites are scary these days. Any ideas?

Getting back into dating can feel totally overwhelming—especially with how different things are these days. I get it, dating sites can seem scary and the whole idea might feel like a lot, but it’s absolutely doable. You’ve got this, and there are ways to make it easier and even fun. Start by focusing on you. Do things that make you feel happy and confident, whether that’s picking up a new hobby, getting out with friends, or treating yourself to something you love. When you’re feeling good about yourself, that energy attracts the right kind of people.

Think about joining a group or trying an activity where you might meet new people naturally. It could be a book club, a cooking class, or even volunteering. These kinds of settings are great because there’s no pressure—it’s just about connecting with others who share your interests. Also, don’t forget about your friends and family! Let them know you’re open to meeting new people. Sometimes the best connections happen through someone you already trust. They might know someone amazing who’s just waiting for the right introduction.

If you’re curious about dating apps but feeling nervous, start slow. Try ones that are more user-friendly and thoughtful, like Bumble or Hinge. Set boundaries for yourself, take breaks if you need to, and treat it like just one way to meet people—not the only way. And hey, it’s okay to laugh at how weird modern dating can be. Focus on connection over perfection. Don’t stress about finding “the one” right away—just enjoy meeting people and having fun conversations. Let things unfold naturally. And if apps aren’t your thing, check out local events or travel groups for singles in your age group. These can be such a low-pressure way to meet like-minded people while doing something fun.

Dating is an adventure, and it doesn’t have to be scary. You’ve got so much to offer, and the right people will see that.

Q: I'm craving  some sort of emotional connection.  I miss that in my life. Is it wrong to hope or am I setting myself up for constant disappointment?

Of course you’re craving emotional connection—it’s one of the most human things ever. And no, it’s not wrong to hope for it. Wanting love and connection is beautiful and shows you’re open to it. But I get it—after disappointments or feeling alone for a while, it’s scary to hope because, what if it doesn’t happen? Here’s the truth: hope isn’t setting yourself up for disappointment—it’s keeping the door open for good things to come your way.

Connection Comes in Many Forms

Emotional connection doesn’t have to mean romantic love right away. It can come from close friendships, meaningful conversations, or even just building a stronger bond with people already in your life. Sometimes those connections are just as fulfilling and can ease the loneliness while you figure out what you want next.

Build a Life You Love

Hope doesn’t mean waiting around for someone to swoop in and change your life. It’s about believing you’re worthy of connection while building a life that makes you happy. Then, if someone amazing comes along, they’re just adding to the goodness that’s already there.

Take Small Steps

If you’re ready, start small. Maybe join a class, pick up a new hobby, or attend events where you can meet like-minded people. You could even try a dating app—no pressure, just as a way to explore what’s out there. It’s all about enjoying the process and being open to possibilities without putting too much pressure on yourself.

It’s Okay to Feel Nervous

Feeling nervous or cautious? That’s normal. But don’t let fear shut you off from the chance for something wonderful. Yes, there’s a risk of disappointment, but there’s also the potential for joy, and you’re absolutely worth that risk. Take it slow and follow what feels right for you.

Be Kind to Yourself

Most importantly, be kind to yourself. You deserve connection, love, and all the good things, whether they come from a partner, a friend, or just deepening the relationship you have with yourself. Hope isn’t setting yourself up for failure—it’s believing that you’re worth the effort and the possibilities.

Q: HELP. There are no good men left...so what now?

I totally get it—dating can feel so discouraging, especially when it seems like all the good ones are taken or nowhere to be found. But trust me, there are good men out there. They might not always be obvious or easy to find, but they’re out there. Let’s figure this out together.

First off, it’s not about how many people are out there—it’s about finding the one person who fits you. You don’t need a ton of “good men,” just the right one for your life. Instead of thinking, “There are no good men left,” try saying, “I just haven’t met the right one yet.” It’s a small shift, but it can open you up to seeing possibilities.

Good men aren’t always in the most obvious places. If dating apps feel overwhelming, look for other ways to meet people—through hobbies, volunteering, local events, or even through friends. Sometimes the best connections happen when you’re just living your life and not actively looking.

Take the pressure off yourself to find “the one” immediately. Just focus on meeting new people, having fun conversations, and seeing where it goes. Even if someone doesn’t turn into a partner, they might add something valuable to your life—or lead you to someone who will.

Think about what really matters to you in a partner. Are you looking for someone kind, funny, adventurous, or thoughtful? Being clear on what you value will help you recognize the right fit when it comes along—even if it doesn’t look exactly how you expected.

And hey, sometimes the right person might not be what you pictured. Be open to surprises. People can come from all kinds of backgrounds and bring something unexpected into your life. Staying open to different personalities and experiences can lead to wonderful connections.

In the meantime, focus on building a life you love. When you’re happy and confident on your own, that energy shines—and people notice it. Plus, you’ll attract the kind of person who values and complements the amazing life you’ve built.

The fact that you’re even thinking about this shows you’re ready for something meaningful. You deserve someone who sees your worth and values everything you bring to the table. If you want tips for meeting people, navigating dating apps, or just need a little encouragement, I’m here for you. You’ve got this, and the right person is out there waiting for someone like you.

Q: I never explored toys....is it time?

If you’re curious about toys, then yep—it might be time! Exploring something new can be super fun and empowering, especially if it helps you reconnect with yourself and discover what you enjoy. There’s no “right” time to start—if you’re feeling curious, that’s your sign.

If you’re new to this, start small. A little bullet vibrator or an external massager is a great way to dip your toes in. They’re simple, easy to use, and perfect for exploring without feeling overwhelming. It’s all about figuring out what feels good to you.

Take your time—this isn’t something you have to rush. Play around with what feels comfortable and see what you like. There’s no “right” way to do this, so just enjoy the process and treat it as an adventure.

If you’re feeling a little unsure, check out some beginner-friendly toys online or visit a store if you’re feeling brave. Some places are super welcoming and have staff who can guide you through your options without it feeling awkward.

Toys aren’t just about pleasure—they’re about getting to know yourself better, building confidence, and even just having a little extra fun. Plus, they can help you relax and relieve stress, which is always a win.

And hey, if you try something and it’s not for you, that’s totally fine too. This is all about you and what feels good in your body and your life. If you’re ready to explore, go for it! 

Q: I feel guilty and 'not so good' about self pleasure, is it normal? is it healthy? Is it beneficial?

First off, let me say—you’re not alone in feeling this way. So many of us have been taught to feel weird or guilty about self-pleasure, but here’s the thing: it’s totally natural, super healthy, and honestly, kind of awesome once you let yourself embrace it.

That guilt? It’s probably coming from old messages you’ve picked up over the years—society, family, or just general taboos around sex. But there’s nothing wrong with exploring your own body and figuring out what feels good. It’s your body, and you deserve to feel good in it.

Self-pleasure is actually really healthy. It can help you relax, improve your mood, and even make it easier to fall asleep. Plus, it’s a great way to get to know yourself better, which can make you feel more confident—whether you’re single or with a partner someday.

It’s also just...fun! It’s a way to take time for yourself, connect with your body, and let go of stress. Think of it as self-care, but with a little extra sparkle. And the best part? There’s no right or wrong way to do it—it’s all about what feels good to you.

If you’re struggling with guilt, try reminding yourself that your body is yours, and there’s nothing wrong with enjoying it. Start small if you need to, and let yourself explore without judgment. It’s not about hitting any goals—it’s about enjoying the journey and feeling good.

You’ve got this, and you deserve all the joy and connection that comes with knowing yourself.

To be continued on part four…